Chatham, VA Vacation Rentals

Explore 14 vacation rentals, homes, and villas in Chatham, VA for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Free Parking and Family-Friendly Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $126 per night and featuring up to 6 bedrooms and 4 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

14 Vacation Rentals in Chatham

Peaceful Chatham Home w/ Grill & Deck

Chatham, VA, US
3 Bedrooms 6 Guests
Aug 25 - 27
$150 night

22 Mi to Caesars Virginia Casino | Dog Friendly w/ Fee | Washer/Dryer Indulge in a memorable stay at 'A Hidden Gem,' a 3-bedroom, 2-bath vacation rental in Chatham! Boasting a ranch-style design, this home offers a front porch and deck ideal for enjoying morning coffee or sunset cocktails. Fire up the grill for a barbecue feast, or cozy up by the fireplace with loved ones. If you feel like exploring, consider taking a day trip to explore Smith Mountain Lake! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed KITCHEN - All major appliances, including dishwasher - Keurig coffee maker, toaster - Cooking basics, spices, trash bags/paper towels, dishware & flatware INDOOR LIVING - Smart TV w/ cable - Dining table OUTDOOR LIVING - Private deck, gas grill - Dining area, fire table - Fenced-in backyard GENERAL - Central heating & A/C - Washer/dryer, iron/board - Linens/towels, complimentary toiletries, hair dryer - Free WiFi - Keyless entry FAQ - 2 exterior security cameras (facing out) - Pet fee (paid pre-trip, dogs only, 1 max) ACCESSIBILITY - Single-story home, 1 minor step to enter PARKING - Driveway (2 vehicles) -- THE LOCATION -- - Quiet, rural location near hiking, hunting, & fishing - 7 miles to White Oak Mountain Wildlife Management Area - 22 miles to Caesars Virginia Casino - 34 miles to Smith Mountain Lake State Park - 18 miles to Danville Regional Airport, 66 miles to Roanoke-Blacksburg Regional Airport, 90 miles to Raleigh-Durham Int'l Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - The single-story home requires 1 minor step to access - Your safety matters. This property features 2 exterior security cameras: 1 camera is located on the front porch facing the front yard, and 1 camera is on the back deck facing the backyard. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion while guests are in residence

Stay Near Averett & Caesars! Cozy Home w/ Patio

Danville, VA, US
2 Bedrooms 4 Guests
Aug 24 - 26
$126 night

Single-Story Home | Fenced-In Backyard | 3 Blocks to Third Avenue Park Roll the dice on a getaway filled with easy fun and together time. Located within 5 miles of Caesars and Averett University, this Danville vacation rental is a convenient home base for sports weekends, college events, and lively nights out. When it’s time to slow things down, curl up in the reading nook, enjoy a cold drink on the patio, or walk to Third Avenue Park for a relaxed family day. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 2 twin beds INDOOR LIVING - TVs - Workspace - Reading nook - En-suite bathroom OUTDOOR LIVING - Backyard - Furnished patio KITCHEN - Refrigerator, stove/oven, dishwasher - Drip coffee maker (coffee provided), toaster, microwave - Cooking basics, dishware/flatware, trash bags/paper towels - Dry bar w/ seating GENERAL - Free WiFi - Central A/C & heat - Hangers - Linens/towels, shampoo, hair dryer ACCESSIBILITY - Single-story home, 4 steps to enter PARKING - Driveway (2 vehicles) - Free street parking (first-come, first-served) -- THE LOCATION -- - 3 miles to Danville Mall, Crossing at the Dan, Averett University - 5 miles to Caesars Virginia - 5 miles to Ballou Park: splash pad, nature trails - 17 miles to Virginia International Raceway - 54 miles to Piedmont Triad International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story home requires 4 steps to enter

Our Point of View - Lakefront home with hot tub, pool table, dock - dog-friendly

huddleston, va, US
3 Bedrooms 6 Guests
Aug 26 - 29
$678 night

As far as vacation destinations go, it’s hard to beat a trip to Smith Mountain Lake. Providing visitors with an area that’s as scenic and tranquil as it is packed with potential for outdoor adventure, you’ll want to make the most of every moment you’re here. Enjoy accommodations that bring the beauty, comfort, and luxury you deserve by booking into Our Point of View during your stay. Be prepared to marvel at the incredible views! While the option is available to spend long days at the lake swimming, paddleboarding, or boating, you’ll be just as inclined to indulge in the many comforts of this luxurious home while you’re here. The wraparound deck makes the exterior of Our Point of View just as inviting as the interior. Spend time lounging under the sun or sipping something savory when the day ends and the stars come out. Beautiful hardwood floors provide the common thread throughout this open-concept home design. A step into the living room brings guests face-to-face with impressive vaulted ceilings and floor-to-ceiling windows, and a large sofa that’s settled wonderfully in front of a towering stone fireplace. When you’re in the mood for a movie night in, the living room is equipped with a large TV and access to high-speed internet. You’ll also find a pool table and a ping-pong table for a little friendly family competition! A dining room table sits directly behind the living room and enjoys equally stunning mountain and water views for an unforgettable mealtime experience. The kitchen is perfect for summoning up culinary creativity with the help of meticulously maintained brick-tile flooring, stainless steel appliances, and long countertops that extend to a sprawling central island. No matter what bedroom you choose in Our Point of View, guests will enjoy the added benefit of deep-pillow and all-new mattresses, and often, private deck access. Each bedroom also has a great view of the lake and mountains! When it comes to keeping clothes clean and packing simple, make the most of the in-home washer/dryer during your stay. Time spent outdoors is essential when visiting Smith Mountain Lake, and when you stay at Our Point of View, you can truly enjoy the beauty of the great outdoors without having to travel far. The exterior deck includes a gas grill that makes it simple to enjoy an open-air meal, while the private hot tub delivers the ideal space to end each and every day on a relaxing note. THINGS TO KNOW Max occupancy is six people over the age of two years old (county and state law). There is no use of the boat lift or slip. Bring your own boat fenders and life vests. Dock Details: Limit 1 boats can be docked during stay. Electrical outlet(s) BOAT LIFTS ARE NOT FOR GUEST USE. You must be 25 years or older to rent this property.

‘Queen Anne Manor’ in Old West End w/ Elevator

Danville, VA, US
6 Bedrooms 12 Guests
Aug 25 - 27
$425 night

Prime Location on Danville's 'Millionaire's Row' | Outdoor Entertainment Space | 5,000 Sq Ft Step into a bygone era of elegance at this historic Danville vacation rental! Spend your afternoons admiring the soaring ceilings and your evenings strolling past the gas-lit lamps of Main Street to a riverfront bistro. This massive manor offers a storied sanctuary where Virginia's architectural heritage comes to life in every room. Your chance to own the 'Row' for a week is here — book now! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 king bed - Bedroom 3: 1 king bed - Bedroom 4: 1 king bed - Bedroom 5: 1 queen bed - Bedroom 6: 2 twin beds INDOOR LIVING - Multiple living & dining areas - 4 entertainment areas, board games, books - TVs in each bedroom - Historic furnishings & decor throughout - Wine fridge - New appliances throughout, Smart thermostats OUTDOOR LIVING - Private upper & lower decks w/ outdoor seating & dining - Partially covered patio, gas fire pit (propane provided) - Backyard w/ gazebo & outdoor seating - Gas grill (propane provided) - Front porch, rocking chairs KITCHEN - Refrigerator, stove/oven, dishwasher - Drip & Keurig coffee makers (starter coffee provided) - Blender, toaster, microwave - Cooking basics, dishware & flatware - Trash compactor GENERAL - Free WiFi, keyless entry - Central A/C & heating - Washer, dryer, laundry detergent, iron & board - Linens & towels - Complimentary toiletries, hair dryer, hangers - New wiring, plumbing & 2 tankless water heaters FAQ - 2 exterior security cameras (facing out) ACCESSIBILITY - Exterior steps required for entry (step-free entry upon request) - 3-story home - All bedrooms on 2nd floor - Elevator available PARKING - Driveway (2 vehicles) - Rear driveway (4 vehicles) - EV charger (available upon request) - Street parking -- THE LOCATION -- - Nestled on 'Millionaire's Row,' one of the most prestigious historic corridors in the South - Located in the Old West End Historic District within walking distance of Danville's thriving and evolving River District - 4 blocks to Danville Museum of Fine Arts and History - Walk to Danville River District: breweries, dining & shops - 1 mile to Averett University - 2 miles to Caesars Virginia - 32 miles to Martinsville Speedway - 52 miles to Piedmont Triad International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking anywhere inside the home - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 3-story home requires exterior steps to enter; however, step-free access can be accommodated upon request. All bedrooms are located on the 2nd floor, but an elevator is present on-site - Your safety matters. This property features 2 external security cameras located on the front door and back door facing the front porch and driveway. These cameras are outward facing and do not look into any interior spaces; they record video and audio when motion is detected

Lake Haven - 5 Bedroom w/ Hot tub and Private Dock

penhook, va, US
5 Bedrooms 14 Guests
Aug 23 - 26
$691 night

Welcome to Lake Haven, our cherished family home nestled in scenic Penhook, a place where family and friends gather and serenity meets. In our retirement, my husband and I decided to take on a massive renovation project. We wanted to create a place for our family and friends to have great times and make fun memories, but then we agreed that we should share it with others so they could enjoy it, too. With a lot of hard labor, long days and nights, and with help from our family and friends aged 2 to 72, we did it! It took two years, but what a labor of love - and well worth it. At Lake Haven, expect a warm and inviting space for all ages. Fall in love with being outside. Lake Haven is situated on a large, private flat lot, providing easy access to the lake and our newly constructed dock. The flat yard makes playing outside games fun and easy. Soak and relax in the hot tub, roast s’mores over the fire pit, take the kayaks out for a tour of the lake, or sunbathe on the lounge chairs on the upper deck. The dock is the cherry on top, with plenty of room to relax in the shade or watch the sun rise and set on the water. Take advantage of the coffee maker, blender, and fridge, and enjoy a cup of coffee or a cocktail. Jump off the floating dock or the water trampoline, or throw in your line to see what you catch. And bring your boat - Lumpkin Marina is less than a mile away for food and gas. Rainy day? No problem. Head inside, where you can get a view of the lake from every room. Head for the game room for some foosball, shuffleboard, or darts. There are also plenty of board and card games to play at the round table, or enjoy the big game on the large-screen TV. If gaming is your thing, check out the Nintendo in the bunk room. Head downstairs and make cocktails at the bar or snuggle up with a good book near one of two fireplaces. With two separate family rooms and two separate gaming/bar areas, there is plenty of room for everyone. There is a fully stocked kitchen upstairs with double ovens to accommodate all the cooking you want to do for a large group, as well as a kitchenette downstairs for extra fridge space. There is a local grocery and convenience store nearby for minor groceries and seasonal items you may have forgotten. The closest chain grocery stores are Food Lion in Gretna, as well as Kroger and Walmart in Rocky Mount. There are several nearby restaurants as well for dining in or carry-out. Smith Mountain Lake is nicknamed the "Jewel of the Blue Ridge", with 580 miles of shoreline. It has become one of the most popular recreational lakes in Virginia - a hub for boating, wakeboarding, water/jet skiing, kayaking, and fishing. With mountain views, the changing of the leaves in the fall, and large families gathering for the holidays, any time of the year is a great time to join us for a slice of lakeside paradise at Lake Haven, where every moment is cherished, and memories are made to last.

Danville Retreat w/ Hot Tub & Cozy Fireplace!

Danville, VA, US
4 Bedrooms 10 Guests
Aug 24 - 26
$273 night

Escape to the charming city of Danville and make unforgettable memories at this spacious 4-bedroom, 4-bath vacation rental. Built in 1907, this beautifully restored Victorian home boasts old-world details with new amenities and a location that puts you just minutes away from top area attractions. Take the kids to the Danville Science Center, explore restaurants and breweries around the River District, try your luck at Caesars Virginia Casino, or tour the Danville Museum of Fine Arts and History! -- THE PROPERTY -- 3,200 Sq Ft | Restored Victorian Home | Quiet Neighborhood | Furnished Porch Bedroom 1: Queen Bed | Bedroom 2: King Bed | Bedroom 3: King Bed | Bedroom 4: 2 Twin Beds | Game Room: Queen Bed | Additional Sleeping: Pack ‘n Play INDOOR LIVING: Smart TVs w/ NFL Sunday Ticket, gas fireplace, game room w/ foosball & poker tables, wet bar, board games, multiple living rooms, formal dining room OUTDOOR LIVING: Large private deck, outdoor dining tables, hot tub, gas grill, outdoor seating, unfenced backyard KITCHEN: Cooking basics, Keurig Duo coffee maker, high chair, coffee grinder, dishwasher, stove/oven, refrigerator, microwave, Crockpot, dishware & flatware, spices, toaster, ice maker, water filter GENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, central heating & air conditioning, in-unit washer & dryer, laundry detergent, hair dryer, iron/board, trash bags & paper towels FAQ: 3 exterior security cameras (facing out), stairs required for access PARKING: Driveway (1 vehicle), free street parking -- THE LOCATION -- CULTURE HUB: Danville Museum of Fine Arts and History (0.2 miles), River District - local restaurants, breweries, entertainment (~1 mile), Danville Science Center (2 miles), Caesars Virginia Casino (2 miles), Blandwood Museum (47 miles) NATURE'S PLAYGROUND: Anglers Park (5 miles), Dan Daniel Memorial Park (6 miles), Gateway Gardens (45 miles), Smith Mountain Lake State Park (54 miles), Falling Creek Park (68 miles) GREEN OASIS: Greensboro Botanical Gardens (48 miles), Greensboro Arboretum (48 miles), Tanger Family Bicentennial Garden (48 miles) THRILLS: Cotton at Riverside Mill (1 mile), Carrington Pavilion (1 mile), JTI Fountain (11 miles), Leesville Lake Marina & Grill (42 miles), Greensboro Science Center (46 miles) AIRPORTS: Raleigh-Durham International Airport (71 miles), Roanoke-Blacksburg Regional Airport (78 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Your safety matters. This property features 3 exterior security cameras. These cameras are outward facing and do not look into any interior spaces. Camera 1 is a doorbell camera on the front door facing the front entry, camera 2 is located on the front porch facing the porch and side yard, and camera 3 is located on the back of the home facing the back deck and hot tub. These cameras actively record video and audio when motion is detected and will be turned on during your stay - NOTE: This property requires stairs to access

Lake Allure - Private Dock, Indoor Pool, and Hot Tub

huddleston, va, US
4 Bedrooms 6 Guests
Aug 24 - 27
$517 night

Allure — A Stunning Lakefront Escape on Smith Mountain Lake Discover Allure, a private, pet-friendly lakefront retreat offering breathtaking views of the Smith Mountain Lake Dam. Featured on the SML Charity Home Tour, this showstopping home perfectly blends comfort, style, and lakeside serenity — making it the ideal getaway for families, friends, or couples seeking a luxurious escape. The Home Spread across three spacious levels, Allure features 4 beautifully appointed bedrooms and 4 spa-inspired bathrooms, comfortably accommodating up to 6 guests (per Bedford County regulations). Relax in the inviting living and dining areas, or unwind in cozy reading nooks surrounded by a curated library and board games for all ages. You’ll also find a private office for those who need to work remotely, a fitness area, and plenty of thoughtful touches that make this home as functional as it is elegant. Outdoor Living Step outside to experience true lake life. The home’s private dock sits on a quiet cove — perfect for swimming, kayaking, floating, fishing, or simply soaking up the sun. Bring your own boat or tie up a rental from one of the nearby marinas; with an average depth of 16 feet, you’ll have deep, calm water right at your doorstep. After a day on the lake, relax in the hot tub, enjoy dinner from the gas grill, or swing gently on the patio overlooking the water. Location Allure is conveniently located just minutes from Smith Mountain Lake State Park, waterfront restaurants, and marinas. Whether you’re looking for outdoor adventure, dining on the water, or a quiet retreat, everything you need is within easy reach. Amenities: Private Dock Hot Tub Pool Kayaks Grill Hotel-quality linens and towels Washer/Dryer High-speed WiFi Onsite parking Pet Friendly (2 dogs max, 50 lbs each) Casago Hospitality Enjoy your stay the Casago Way — with flexible check-ins, contactless arrival, and concierge-style hospitality. The fully stocked kitchen includes convenient extras like foil, storage bags, paper products, dish pods, and propane. Every Casago home is professionally cleaned and sanitized to CDC and VRMA standards, with additional supplies provided for your peace of mind. Good to Know Non-smoking property No events or parties permitted Boat lift not available for guest use Exterior cameras (driveway and waterfront only) for security Guests are responsible for pet cleanup and damages Pets must be leashed outdoors and not left unattended indoors unless crated No pets on beds or furniture; please dry wet pets outside before entry

Doc Side - Serene lakefront home with dock, hot tub, pool table & beautiful views

huddleston, va, US
3 Bedrooms 6 Guests
Aug 23 - 26
$192 night

If you’re looking for a serene and calming vacation, look no further than this lovely lakefront getaway! This home boasts a dock, so feel free to rent a boat and sail across the pristine waters of Smith Mountain Lake. After a fun-filled day, simmer down in the private hot tub with a couple of drinks in hand. Just across the cove lies Parkway Marina, where you can rent a boat and take your group across the glimmering waters. You’ll be an easy drive from Ramulose Ridge Vineyards, where you and your guests can taste some delicious local wine and even take some home for yourselves. Also within a short drive is ’the Bridge,’ with tons of restaurants and eateries right at your fingertips. Hop into your favorite swimsuit, then take a dip in the refreshing waters of the lake to cool off. Return home to unwind in the spacious living area and lie down for a quick nap. You’ll be provided with your own gas grill, so throw some patties on for some classic American barbecue when you get hungry. In the evenings, challenge your loved ones to games of nine ball at the private pool table inside. There’s a little something for everyone at this incredible home! Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. A limit of one boat can be docked here during your stay. There are electrical outlets. The boat lifts are not for guest use. All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Permit number: MP-000089-2026 You must be 25 years or older to rent this property.

Jewelbox Cottage - Dog-friendly Lakefront home with private dock, canoe & SUPs

huddleston, va, US
3 Bedrooms 6 Guests
Aug 23 - 26
$216 night

Looking for a waterfront cottage on a flat lot? This whimsical lakefront home is mere steps from the lake, with no steep hillside to trek down to the water. The sand beach allows for children and adults to walk right in, play on the shore, and easily launch canoes and paddleboards. You’ll love the private dock with a slide and jumping platform. Relax on the porch with rocking chairs to enjoy the sunset over the lake. Your magical outdoor dining area in a shaded lush garden includes a large table with plenty of seating and serving room on a cobblestone patio set under evening twinkle lights. Ready for family fun, your three-bedroom, two-bath home has a large mudroom/laundry room and a firepit with ample Adirondack chairs overlooking the lake. Paddleboards and a three-person canoe await you, with adult life jackets. There’s also a ping-pong table as well as fishing rods and supplies. Inside, the sparkling full kitchen boasts stainless steel kitchen appliances, a long center island table, plus a dining table for your meals. Extras include a slow cooker, mixers, ample tableware and serving ware, and all the gadgets for easy meal prep. The newly completely renovated bathrooms feature natural stone and river rock shower floors and rainfall shower heads. The great sectional sofa and lovely wooden beams complement the main living area with plenty of ceiling fans throughout. The high-speed WiFi is wonderful here - the best on the lake and perfect for video streaming, work from home, and social media. Flick on the smart TV with a DVD player to stream all your favorite shows. This home is stocked with movies, books, and games for the whole family for hours of enjoyment and family fun. THINGS TO KNOW Max occupancy is six people over the age of two years old (county and state law). There is no use of the boat lift or slip. Bring your own boat fenders and life vests. Dock Details: Limit 1 boat can be docked during stay. No electrical outlets. BOAT LIFTS ARE NOT FOR GUEST USE. Permit number: MP-000383-2025 You must be 25 years or older to rent this property.

Lake Reflections - Lakefront with private dock, & Fire pit

huddleston, va, US
4 Bedrooms 4 Guests
Aug 23 - 26
$326 night

Welcome to Lake Reflections, your peaceful waterfront escape on beautiful Smith Mountain Lake. This charming pet-friendly home (2 dogs max, 50 lbs each) offers 2 bedrooms and 2 baths, cozy interiors, and stunning lake views that set the scene for the perfect family getaway. Step outside to generous outdoor living spaces and a gentle walkway leading to your private dock, where you can relax by the water, fish, swim, or launch your boat rental for a day of exploring the lake. With an average water depth of 14 feet, this spot is perfect for soaking up those classic SML moments. You’re also just minutes from Smith Mountain Lake State Park, marinas, boat launches, gas docks, restaurants, and more. Inside, you’ll find inviting comfort and convenience throughout—including a well-stocked kitchen, hotel-quality linens, fast WiFi, and a washer/dryer. Evenings are best spent around the fire pit, sharing stories under the stars as the lake reflects the night sky. With thoughtful Casago touches—contactless check-in, concierge-style service, flexible stays, and CDC-standard cleaning—you can relax the moment you arrive. Home Information Sleeping Setup (Max Occupancy: 4 — required by Bedford County): 1 King 2 Queen 2 Twin Amenities: Private dock Fire pit WiFi Hotel-quality linens and towels Washer/dryer Onsite parking Pet friendly (2 dogs max; pet rules apply) Well-stocked kitchen with essentials (foil, bags, trash bags, detergents, paper products, propane, etc.) Policies: Non-smoking home No events or parties 2-dog limit; no other animals Boatlift not available for guest use Pets must be leashed outdoors, crated if left alone, kept off furniture, and dried before entering Additional cleaning fees apply for pet hair, odors, or damage Exterior cameras monitor driveway and waterfront for security Experience Smith Mountain Lake the Casago Way — clean, comfortable, and truly relaxing.

Lake Pleasant - Lakefront, Private Dock, Game room

huddleston, va, US
4 Bedrooms 4 Guests
Aug 21 - 24
$339 night

Lake Pleasant Welcome to Lake Pleasant, a tranquil waterfront retreat tucked into a quiet cove on beautiful Smith Mountain Lake. Perfect for a peaceful couples’ getaway or a small-family escape, this inviting 4-bedroom, 2.5-bath home blends comfort, privacy, and lakeside charm. Step inside to soaring ceilings, abundant natural light, and serene water views that greet you from the main living areas. The comfortable furnishings, warm design, and spacious layout make it easy to relax, recharge, and settle into lake life. Enjoy memorable meals on the upper or lower decks, unwind with a good book, or gather in the game room for friendly fun. Just steps from the home, a gentle path leads you to the private dock—your launching point for swimming, floating, paddling, or simply soaking in the peacefulness of the cove. Bring your own boat or tie up a rental, or take the provided paddle boat for a scenic cruise. Average water depth at the dock is 7 feet. Located only minutes from Smith Mountain Lake State Park, marinas, gas docks, and local restaurants, this home offers both seclusion and convenience—perfect for enjoying the best of SML. Beds: King, Queen Occupancy: Limited to 4 guests per Bedford County regulations Amenities Fire pit Hotel-quality linens and towels Paddle boat Private dock Onsite parking WiFi Washer/dryer Spacious decks with lake views Enjoy SML the Casago Way Flexible stays Contactless check-in Concierge-style service Well-stocked kitchen with essentials: foil, storage bags, dish pods, trash bags, paper products, propane, and more Professionally cleaned and sanitized per CDC and VRMA guidelines Notes All Casago homes are non-smoking No pets or ESAs allowed (ask us about pet-friendly homes) No events Boat lift not available for guest use Exterior cameras (if present) monitor driveway and waterfront only

Otter Crossing - Spacious dog-friendly house w/fire pit, deck, patio & grill

huddleston, va, US
3 Bedrooms 8 Guests
Aug 21 - 24
$371 night

Escape to this stunning lakefront house in Huddleston, VA, where you’ll be greeted by breathtaking views and a serene atmosphere. Nestled on the shores of the lake, this unique property offers a tranquil retreat with a stone paver path leading to a private dock where you can enjoy the calm waters for kayaking and swimming. The house boasts unique mantels and tree trunk supports in the basement bar area, adding a touch of charm to your stay. Inside, you’ll find a well-appointed home with all the amenities you need for a comfortable vacation. Relax in the cozy living room or whip up a delicious meal in the fully equipped kitchen complete with modern appliances. Enjoy your morning coffee on the balcony overlooking the lake, or grill up some BBQ on the patio while taking in the mountain views. The sunroom has two live edge bar tables with stools perfect for sipping coffee and taking in the views. This family-friendly house offers plenty of entertainment options, from board games to Netflix streaming on the TV. The spacious deck is perfect for outdoor dining or simply soaking up the sun. Bring your own wood and enjoy an evening relaxing around the fire-pit. With multiple bedrooms including a queen bed and twin bed, there’s plenty of space for the whole family to unwind after a day of exploring the area. Located near golf courses, wineries, and restaurants, this lakefront retreat is the perfect home base for your Huddleston getaway. Whether you’re seeking a relaxing escape or an adventure-filled vacation, this house has something for everyone. Book your stay now and experience the beauty of lakeside living in Virginia. Permit number: MP-000549-2025 You must be 25 years or older to rent this property.

The Lodge on Smith Mountain Lake - Lakefront cabin w/ dock, hot tub & pool table

huddleston, va, US
4 Bedrooms 8 Guests
Aug 21 - 24
$1,152 night

This new vacation rental, with all new furniture, offers all the comforts of home in a lodge-style setting. An oversized covered porch, with ceiling fans and a dining area, stretches from one end of the home to the other, overlooking the clear waters of Smith Mountain Lake with a fantastic view of Smith Mountain. Outside, you have an easy path to the shoreline with an oversized private dock in a quiet cove. Guests can enjoy two kayaks and a paddleboard to explore the cove and beyond. A firepit area allows for continued enjoyment of the view or for making s’mores. A hot tub, beneath the covered porch, allows for more relaxation while enjoying the view in any weather. The rental is close to Smith Mountain Lake State Park for great hiking, camping, and use of their beach. You’ll have easy access to launch your boat or watercraft from Parkway Marina just down the street. There is plenty of room to tie up a boat from the floaters, with a jet ski ramp also available. The Lodge at Smith Mountain Lake is laid out wonderfully for a vacation rental. You enter into the open and inviting great room with a stone fireplace, wood beams, and floors. From the great room, you step out onto an oversized, covered porch with million-dollar views of the lake and mountain. The layout offers plenty of seating around the fireplace and TV. You’ll also find a well-equipped kitchen, a breakfast bar, and a large farmhouse dining table for meals. The primary suite is located on the main level, with views of the lake and mountain. The sliding doors from the en suite walk out to the covered porch. Upstairs, two large bedrooms are offered, each with a private bath and views of the lake and mountain. The fourth bedroom is located on the lower level and offers lakefront views and a private bath. Also on the lower level is the game room which has a pool/ping-pong table, a fireplace, a TV, games, an extra refrigerator, and seating for the group. High-speed Xfinity WiFi is provided for both work and play. THINGS TO KNOW Max occupancy is eight people over the age of two years old (county and state law). There is no use of the boat lift or slip. Bring your own boat fenders and life vests. Dock Details: Limit 1 boats can be docked during stay. Electrical outlet(s) BOAT LIFTS ARE NOT FOR GUEST USE. Permit number: MP-000385-2025 You must be 25 years or older to rent this property.

Vacation Rentals in Chatham by Amenities & Features

Get to Know Chatham

Chatham, Virginia, is a charming small town that offers visitors a slice of classic Americana with a touch of Southern hospitality. Nestled in Pittsylvania County, Chatham's appeal lies in its rich history, picturesque landscapes, and a tranquil atmosphere that provides a respite from the hustle and bustle of city life. History enthusiasts will appreciate Chatham's well-preserved architecture and historical sites. The Pittsylvania County Courthouse, a stately Greek Revival structure, stands as a testament to the town's past. The Chatham Historic District, with its beautiful homes and buildings dating back to the 18th and 19th centuries, offers a delightful walk through time. For those interested in the educational legacy of the South, Chatham is home to Chatham Hall, an all-girls college preparatory boarding school with a stunning campus and a reputation for academic excellence. Hargrave Military Academy is another notable institution, emphasizing leadership and character development in its storied setting. Nature lovers will find solace in the scenic beauty surrounding Chatham. The nearby Smith Mountain Lake and its state park provide opportunities for boating, fishing, and hiking, while the Dan River is perfect for a leisurely day of kayaking or canoeing. The region's rolling hills and lush farmland offer picturesque drives and the chance to visit local vineyards and sample some of Virginia's fine wines. Agriculture plays a significant role in the area's culture, and visitors can experience this firsthand at local farmers' markets and seasonal festivals that celebrate the town's agricultural heritage. The Chatham First Saturdays Farmers Market is a great place to mingle with locals and enjoy fresh produce, homemade goods, and artisanal crafts. Chatham's dining scene, though modest, reflects its Southern roots with comfort food staples and friendly service. Local cafes and restaurants serve up dishes that are sure to satisfy those looking for a taste of the South. Each year, Chatham hosts events that bring the community together, such as the Historic Chatham Cavalier Cup Polo Match and the Pittsylvania County Fair, offering fun for the whole family. In essence, Chatham, Virginia, is a destination that promises a peaceful getaway with a touch of history, nature, and Southern charm. It's a place where visitors can slow down, enjoy the simple pleasures, and leave feeling refreshed and connected to the heart of rural Virginia.
Chatham, Virginia, experiences a humid subtropical climate, which means you can expect hot summers, mild winters, and precipitation spread throughout the year. The weather patterns here are typical of the mid-Atlantic region of the United States, offering a full four-season experience that can be both diverse and pleasant. The summer months, from June to August, are warm to hot with average high temperatures ranging from the mid-80s to low 90s Fahrenheit (around 29-34°C). Humidity can be quite high during this time, which can make the heat feel more oppressive. These months also see the most precipitation, with occasional thunderstorms that can provide a refreshing break from the heat. Autumn, from September to November, brings a welcome change with cooler temperatures and less humidity. The highs range from the 70s in early September down to the 50s by late November (around 21-15°C). This is a beautiful time to visit as the leaves change color, creating picturesque landscapes that are a delight for photographers and nature lovers alike. Winter, from December to February, is generally mild compared to more northern regions. Average high temperatures hover around the upper 40s to low 50s Fahrenheit (around 9-12°C), with lows dipping into the 20s and 30s (-6 to 2°C). Snowfall is possible but not as heavy or frequent as in more northern states. This season is quieter in terms of tourism, offering a peaceful experience of the area's natural beauty. Spring, from March to May, sees a gradual warming with temperatures ranging from the 50s in early March to the 70s by late May (around 10-21°C). This season is marked by blooming flowers and the reawakening of the local flora and fauna. Rainfall is moderate, and the weather can be quite pleasant, making it a great time for outdoor activities. The most popular time to visit Chatham is during the spring and fall when the weather is most comfortable for exploring the outdoors and enjoying the natural beauty of the region. These seasons offer a delightful mix of pleasant temperatures, lower humidity, and the visual splendor of the changing seasons. Whether you're looking to enjoy the vibrant fall foliage or the fresh blooms of spring, these are the ideal times to experience the best of Chatham's climate.
Chatham, Virginia, may not be the first destination that comes to mind for a cultural enthusiast, but this charming small town in Pittsylvania County offers a quaint and intimate experience of the arts, history, and local customs. Begin your cultural exploration at the Chatham Hall, an Episcopal girls' boarding school with a historic campus that dates back to the 19th century. The school often hosts arts events and speakers that are open to the public, providing a glimpse into the educational culture of the region. For a deep dive into local history, the Pittsylvania County History Research Center and Library is a treasure trove of genealogical records and historical documents. It's an excellent resource for those interested in the area's past and the stories of the people who have shaped it. Art enthusiasts will enjoy the Chatham First art initiative, which aims to beautify the town with public art. Stroll through the town to see murals and sculptures that add a touch of creativity to the local landscape. While Chatham may not have large art galleries, the community's commitment to the arts can be seen in these public displays and in the local businesses that support regional artists. Live music can be found at local venues and events, particularly during the summer months when outdoor concerts and festivals bring the community together. The town's proximity to Danville, just a short drive away, expands the options for live performances and cultural events. Chatham's local customs are best experienced during its annual events, such as the Historic Chatham Cruise-In, where vintage car enthusiasts gather to showcase their vehicles, evoking a sense of nostalgia and community spirit. The Chatham Sartomer 5K race is another local tradition, bringing residents and visitors together in a celebration of health and community. For a taste of local cuisine, visit the Chatham Farmers Market, where you can sample fresh produce and homemade goods that reflect the agricultural heritage of the region. The town's restaurants and cafes also offer Southern hospitality and the chance to enjoy regional dishes in a cozy setting. While Chatham may offer a more subdued cultural experience compared to larger cities, its charm lies in the personal connections you can make with the arts, history, and customs of this Southern community. It's a place where culture is lived and appreciated on a human scale, inviting visitors to slow down and savor the richness of local life.
Chatham, Virginia, may not be the largest town on the map, but it offers a quaint and charming experience for families traveling with children. This small town is nestled in Pittsylvania County and provides a peaceful retreat with a touch of history and nature that can be enjoyed by all ages. One of the main attractions in Chatham is the Chatham Hall, a historic girls' boarding school with beautiful grounds that can be admired during a leisurely walk. While the school itself isn't a playground, the surrounding area offers a serene environment where children can enjoy the outdoors. For a dose of history, the Pittsylvania County Historical Society operates several museums in the area, including the 1813 Clerk's Office and the 1853 Callands Clerk's Office and Jail. These sites offer a glimpse into the past and can be educational for older children interested in history. Outdoor enthusiasts will enjoy Chatham's proximity to the scenic Staunton River State Park, which is just a short drive away. The park offers a variety of activities including hiking, fishing, and boating. Children can explore the playgrounds, splash in the swimming pool, or participate in the park's nature programs. The town also hosts community events throughout the year, such as the Chatham Cruise-In, where families can view classic cars and enjoy the festive atmosphere. These events often include activities specifically for children, like face painting and games. For a sweet treat, families can visit the local ice cream shop or one of the charming cafes in town, which often have kid-friendly menu options. The small-town feel of Chatham means that these establishments are welcoming to families and provide a cozy spot to relax and refuel. While Chatham may not have the large-scale attractions of a big city, it offers a gentle pace and family-friendly atmosphere that can be a welcome change for those looking to escape the hustle and bustle. Its natural beauty, historical sites, and community spirit make it a pleasant stop for families with children seeking a quieter adventure.
Chatham, Virginia, nestled in the rolling hills of Pittsylvania County, is a serene destination for outdoor enthusiasts and nature lovers. This quaint town and its surrounding areas offer a variety of natural wonders and activities that allow visitors to connect with the great outdoors. One of the highlights near Chatham is the Smith Mountain Lake, a sprawling reservoir that is a haven for water sports enthusiasts. With over 500 miles of shoreline, it's perfect for boating, fishing, kayaking, and paddleboarding. The lake's clear waters are also ideal for swimming during the warmer months. For those who prefer land-based activities, the nearby Smith Mountain Lake State Park provides ample opportunities for hiking, picnicking, and wildlife observation. The park's trails meander through hardwood forests and offer picturesque views of the lake and its coves. Birdwatchers will delight in the variety of species that call this area home. Just a short drive from Chatham, the scenic Blue Ridge Parkway offers breathtaking vistas and a multitude of hiking trails. The parkway is renowned for its stunning display of wildflowers in the spring and vibrant foliage in the fall. Hiking trails along the parkway range from easy strolls to challenging treks, such as the hike to the summit of Sharp Top Mountain, which rewards adventurers with panoramic views. Anglers will find solace in the Banister River, a peaceful waterway that flows through the heart of Pittsylvania County. The river is stocked with bass, catfish, and other freshwater species, making it a popular spot for fishing. Canoeing and kayaking along the gentle currents of the Banister provide a tranquil way to explore the region's natural beauty. For a unique outdoor experience, visit the Chatham's local vineyards, where the rolling landscapes not only produce fine wines but also offer a picturesque setting for a leisurely afternoon. Wine tastings and tours allow visitors to savor the local flavors while enjoying the pastoral views. Lastly, the White Oak Mountain Wildlife Management Area is a hidden gem for those seeking solitude and a deep connection with nature. This expansive area is home to diverse habitats, including upland hardwood forests and open fields, making it a prime location for hunting, hiking, and observing Virginia's native flora and fauna. Chatham, Virginia, may be small in size, but it's rich in natural beauty and outdoor opportunities. Whether you're casting a line in a serene river, hiking through lush forests, or simply enjoying the tranquility of the countryside, Chatham offers a peaceful retreat into nature's embrace.
Chatham, Virginia, is a quaint and historic town that offers a serene escape from the hustle and bustle of city life. While it may not have the extensive transportation networks of a major city, there are still several ways for travelers to arrive, depart, and explore this charming destination. Most visitors traveling to Chatham will likely arrive by car. The town is situated within driving distance of several major cities, including Roanoke, VA, about an hour away, and Greensboro, NC, which is approximately an hour and a half's drive. For those coming from farther afield, the nearest major airport is Lynchburg Regional Airport, located about 45 minutes away by car. From there, renting a car or using a taxi service would be the most convenient options to reach Chatham. Once in Chatham, getting around is relatively straightforward. The town itself is small and can be quite walkable, especially in the downtown area where you can enjoy local shops, dining, and the historic Pittsylvania County Courthouse. For longer distances or for those who prefer not to walk, having a car is beneficial. There is no public transportation system within Chatham, so a car will provide the flexibility to explore the surrounding areas, including nearby parks and natural attractions. For those interested in regional exploration, Chatham serves as a good base to visit nearby attractions such as the Smith Mountain Lake, the Blue Ridge Parkway, and the Danville Science Center. These sites are best accessed by car, as public transportation options are limited in this more rural part of Virginia. Cycling can also be a pleasant way to enjoy the local scenery, with several country roads offering peaceful routes. However, it's important to note that these roads may not have dedicated bike lanes, so cyclists should be cautious and aware of traffic. In summary, while Chatham may not offer the transportation amenities of a larger city, its accessibility by car and the walkability of its downtown area make it a pleasant destination for those looking to enjoy a slower pace. Renting a car is the most practical way to explore the town and the beautiful countryside that surrounds it.

Chatham FAQs

Chatham, Virginia, offers a variety of activities for visitors. You can explore the historic Chatham Hall, an all-girls preparatory school with beautiful grounds. The town is also home to Hargrave Military Academy, which has a rich history and campus tours. For outdoor enthusiasts, there's the nearby Cherrystone Lake for fishing and boating, and the scenic White Oak Mountain Wildlife Management Area for hiking and wildlife observation. Additionally, Chatham hosts several charming bed and breakfasts, antique shops, and local eateries that provide a taste of Southern hospitality.
Chatham boasts a selection of delightful dining options. Some of the local favorites include Reid Street Gallery, which offers a cozy café atmosphere and art exhibits, and the Chatham Cafe, known for its home-style cooking. For a more upscale dining experience, try the historic Chatham Manor restaurant, which serves Southern-inspired cuisine in an elegant setting.
Yes, Chatham is rich in history. The Pittsylvania County Courthouse, built in 1853, is a notable landmark. The Chatham Historic District includes several well-preserved 19th-century buildings. Visitors can also explore the Watson Memorial Library and the Chatham Train Station, which contribute to the town's historical charm.
Chatham offers a range of accommodations, from charming bed and breakfasts like the Oaks Victorian Inn to local inns such as the Chatham Inn. There are also several vacation rentals and a few motels in the area for those looking for more budget-friendly options.
Chatham hosts several annual events that attract visitors. The Chatham First Saturdays are popular, featuring local crafts, food, and music. The Pittsylvania County Fair and the Historic Chatham Cruise-In car show are also major draws. Additionally, the town celebrates its heritage during the Chatham Sartomer 5K and the Olde Dominion Agricultural Complex events.
Absolutely! Chatham is a great destination for families. The town offers several parks, such as the Chatham Community Park, which has playgrounds and picnic areas. The White Oak Mountain Wildlife Management Area provides opportunities for family hikes and nature exploration. Additionally, the local events and festivals often have activities and entertainment suitable for children.

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Vacation Rentals Near Chatham

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