Large group vacation rentals in Winhall, VT

Explore 149 large group vacation rentals, homes, and villas in Winhall, VT for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Homes with Free Parking and Best Affordable Homes. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $79 per night and homes offering up to 8 bedrooms and 5 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

149 Great for Groups in Winhall

Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!

Winhall, VT, US
4 Bedrooms 7 Guests
Aug 25 - 28
$639 night

Plan for plenty of outdoor fun when you book this Winhall vacation rental for your next exciting Vermont getaway! With a furnished deck, private wood-burning fire pit, and prime location just minutes from top-rated ski resorts, this 4-bedroom, 4-bath house is perfect for a fun family trip or memorable stay with friends. Enjoy breakfast with stunning mountain views before heading out to hit the slopes at Stratton Mountain Resort. Or, spend warmer days exploring the trails at Jamaica State Park! -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | In-Unit Laundry | Gas Grill | Fenced Backyard | 9 Mi to Jamaica State Park Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Bunk Beds | Bonus Room: Full Bed INDOOR LIVING: Smart TVs, dining table, en-suite bathrooms, walk-in showers, shower/tub combo OUTDOOR LIVING: Private deck, wood-burning fire pit, outdoor dining, mountain views, hot tub KITCHEN: Refrigerator, coffee maker, stove/oven, microwave, dishwasher, dishware & flatware, cooking basics GENERAL: Keyless entry, self check-in, free WiFi, central heating & A/C, 2 washer & dryer sets, towels/linens, trash bags/paper towels, complimentary toiletries FAQ: Stairs required for access, pet fee (paid pre-trip) PARKING: Heated garage (2 vehicles), driveway (4 vehicles) -- THE LOCATION -- WINTER SPORTS: Stratton Mountain Resort (6 miles), Coca Cola Tube Park (7 miles), Bromley Mountain Ski Resort (8 miles), Magic Mountain Ski Area (11 miles) OUTDOOR ADVENTURE: Stratton Adventures - ATV/snowmobile tours (7 miles), Ball Mountain Dam Hiking Area (9 miles), Jamaica State Park (9 miles), Lye Brook Falls (12 miles), Hamilton Falls (21 miles) LOCAL GOLF COURSES: Stratton Mountain Golf Course (4 miles), Ekwanok Country Club (15 miles) AIRPORTS: Albany International Airport (72 miles), Bradley International Airport (114 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 - Pet friendly w/ $100 fee (+ fees & taxes, 2 pets max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access

Winhall Woodland House | Winhall Home w/ large deck - near Stratton & Bromley

Winhall, VT, US
4 Bedrooms 7 Guests
Aug 25 - 27
$309 night

Escape to the beauty of Winhall with our charming house, complete with a large deck that invites you to unwind and soak up the tranquility of the surroundings. Located near the renowned Stratton and Bromley Mountains, as well as the picturesque Beaver Pond, this home offers an ideal retreat for outdoor enthusiasts and nature lovers. Step inside and be welcomed by a beautifully decorated interior that radiates warmth and comfort. The open layout seamlessly connects the living, dining, and kitchen areas, creating a welcoming space for gathering and relaxation. Natural light fills the rooms, enhancing the inviting ambiance. The house’s prime location near Stratton and Bromley opens up a world of adventure. Whether you’re an avid skier or snowboarder, the slopes await, offering exhilarating experiences during the winter months. In the warmer seasons, explore the nearby Beaver Pond, where fishing, hiking, and peaceful contemplation amidst nature’s splendor await. Return to the house and revel in the expansive deck, a perfect oasis for enjoying the fresh mountain air and breathtaking views. Whether you’re savoring a delicious meal, sipping your morning coffee, or simply unwinding with a book, the deck provides an idyllic setting for relaxation and rejuvenation. With comfortable bedrooms and modern amenities, this house ensures a cozy retreat for restful nights and leisurely days. Whether you’re seeking a romantic getaway or a family vacation, this home offers a peaceful haven amidst Winhall’s natural beauty. Escape to our charming Winhall house with its large deck, close proximity to Stratton, Bromley, and the captivating Beaver Pond. Immerse yourself in the perfect blend of natural splendor and comfortable living, creating cherished memories that will last a lifetime. Town of Winhall STR License Number: 003312 Vermont Meals and Room Tax Number: MRT-11472019

Elegant house in quiet neighborhood, close to ski mountains, gas fireplace, wifi

Winhall, VT, US
4 Bedrooms 7 Guests
Aug 25 - 27
$309 night

Escape to this charming four-bedroom house nestled in the serene community of Winhall, VT, offering close proximity to popular ski resorts like Stratton (10-minutes), Bromley (8-minutes) and Mt. Snow (30-minutes), as well as the charming town of Manchester (15-minutes) with vintage shops, country stores, cafes, bookstores, and more. Situated on a spacious 1.6-acre corner lot, this home provides a peaceful retreat with easy access to outdoor adventures. The main floor features a large primary bedroom with an en-suite bathroom, providing convenience and privacy. Upstairs, three generously sized bedrooms share a spacious bathroom, making this home ideal for families or groups of friends. The open concept layout of the kitchen, dining room, and living room creates a welcoming space for entertaining and relaxing after a day of exploring. Enjoy a plethora of amenities during your stay such as a fully equipped kitchen with modern appliances, a private washer/dryer, gas fireplace, internet access, and more. Cozy up by the gas fireplace in the living room, stream your favorite movie or TV show, or challenge your companions to a friendly board game night. With other attractions like Riley Rink at Hunter Park, Manchester Country Club, and Magic Mountain Ski Area within easy reach, you’ll have plenty of options for outdoor fun. Whether you’re into skiing, golfing, hiking, or simply exploring the charming town of Winhall, this home serves as the perfect base for your Vermont getaway. Book your stay at this inviting Winhall retreat and create unforgettable memories with your loved ones in this picturesque New England setting. Experience the beauty of Vermont and all it has to offer from the comfort of this lovely vacation home. Town of Winhall STR License Number: 003314 Vermont Meals and Room Tax Number: MRT-11472019

Stratton Shuttle Access! Vermont Mountain Hideaway

Winhall, VT, US
4 Bedrooms 8 Guests
Aug 30 - Sep 1
$395 night

Pet Friendly w/ Fee | Sauna & Hot Tub for Chilly Nights | Forested Setting Alpine atmosphere and modern comforts await at this 4-bed, 3.5-bath Winhall vacation rental! The home offers fun for your whole group — barbecue on the patio, let the kids play games in the upstairs lounge, and practice your serve at the community tennis courts. Ready to ramp up the adventure? Scenic slopes, fall foliage, waterfall hikes, and more can all be found in the surrounding Green Mountain National Forest. -- THE PROPERTY -- MRT-11153470-001 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Bedroom 3: 2 twin beds - Bedroom 4: 2 twin beds COMMUNITY AMENITIES - Tennis courts - Pond, picnic area - Ski shuttle INDOOR LIVING - Smart TV, fireplace - Dining table - Sauna - Xbox, darts OUTDOOR LIVING - Patio, gas grill (propane provided) - Hot tub, outdoor seating, umbrella - Fire pit, pond views KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Drip coffee maker, Keurig (pod provided), toaster, blender - Cooking basics, dishware & flatware, trash bags & paper towels GENERAL - Central heating & A/C - Towels & linens, complimentary toiletries, hair dryer - Washer & dryer - Free WiFi - Keyless entry FAQ - 4 exterior security cameras (facing out) - Pet fee (paid pre-trip)  ACCESSIBILITY - 2-story home, 4" threshold step to enter - 2 bedrooms & 2 full bathrooms on 1st floor PARKING - Driveway (6 vehicles) - No street parking -- THE LOCATION -- - 5 miles to Stratton Mountain Resort - 8 miles to Bromley Mountain - 9 miles to Londonderry: cafes, restaurants, shops - 20 miles to Emerald Lake State Park - 72 miles to Albany 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 - Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 1 pet max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home can be accessed through the side door with a 4" threshold step; there are 2 bedrooms and 2 full bathrooms on the 1st floor - Your safety matters. This property features 4 exterior security cameras. Camera 1 is on the southeast corner of the house facing the driveway. Camera 2 is on the front door facing the driveway. Camera 3 is on a tree in front of the house facing the front entry. Camera 4 is on the southwest corner of the house facing the hot tub. The cameras are outward facing and do not look into interior spaces. The cameras record video when activated by motion

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Winhall, VT, US
3 Bedrooms 6 Guests
Aug 31 - Sep 2
$823 night

Secluded Natural Surroundings | Sun-Soaked Living Space Enjoy all-season adventures just beyond your doorstep at this Winhall 3-bed, 2.5-bath vacation rental in the coveted Stratton Mountain Forest Farms neighborhood. The Scandinavian ski house features a tranquil nature-inspired design, Nordic furnishings, and a deck overlooking the Green Mountain National Forest. After a day on the slopes, explore Stratton Village or head back to 'Eagle View' and watch the sunset. Book today! -- THE PROPERTY -- MRT-11153470-001 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 bunk bed (twin/queen) - Bedroom 3: 1 bunk bed (twin/queen) - Loft: 1 twin futon INDOOR LIVING - 75" TV, flat-screen TVs - Dining table, fireplace - 6-foot soaking tub - Newly built, cedar wood 25' ceilings, picture windows - Nordic-inspired furnishings, open-floor layout OUTDOOR LIVING - Deck, Adirondack chairs - Stream on property, Stratton Mountain views - Southwestern exposure KITCHEN - Dishwasher, refrigerator, stove/oven, microwave, pantry - Keurig coffee maker, toaster - Cooking basics, high-end cookware, dishware & flatware, trash bags & paper towels - Modern chandelier GENERAL - Central heating & A/C - Towels & linens, complimentary toiletries, hair dryer - Washer & dryer, hangers - Free WiFi (high speed, Starlink) FAQ - 2 exterior security cameras (facing out) ACCESSIBILITY - 2-story cabin, exterior staircase to enter - Bedroom & bathroom on 1st floor PARKING - Driveway (5 vehicles) -- THE LOCATION -- - Nearby outdoor activities: skiing, biking, hiking, kayaking, golfing, snowshoeing, ice skating, horseback riding - Stratton Mountain firework views from the deck for select holidays - 4 miles to Stratton Sun Bowl Base Lodge & Stratton Mountain Resort - 4 miles to Stratton Village: yoga, wine & beer festivals, live entertainment - 10-13 miles Bromley Mountain Ski Resort & Magic Mountain Ski Area - 13 miles to Manchester - 16 miles to Weston Theater Company - 14 miles to Appalachian Trail access - 74 miles to Albany 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 or vaping anywhere on the property - 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 2-story cabin requires an exterior staircase to enter. A bedroom and full bathroom are on the 1st floor - The property and surrounding area are prone to severe weather, including snow, ice, mud, and strong winds. Please ensure your vehicle is properly equipped with suitable tires, use caution while walking, and supervise children at all times - Your safety matters. This property features 2 exterior security cameras: camera 1 is a Ring doorbell device with an exterior security camera facing the front outdoor entry, and camera 2 is a security camera located on the side door facing out. The cameras do not look into any interior spaces. The cameras record video and sound when motion is detected by the device

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton, VT, US
1 Bedrooms 3 Guests
Aug 25 - 27
$88 night

This Stratton Mountain condo is all about location as it is right in the center of Stratton Village and within walking distance of restaurants, shops, and the lift! The condo has features to keep you comfortable no matter the season with its plush sofa, gas fireplace for warm snuggles with a glass of wine, or central AC for those sweaty days spend exploring the terrain. Food is never far away with the local restaurants, but if you need some time in, the full kitchen is there for a quiet and relaxing night. Take a sip of your morning coffee on your private balcony and sit down on one of the chairs available as you take in the views of the complex and enjoy the cool breeze. Book Long Trail House: 368 and you’ll be granted access to shared on-site amenities that include swimming pools, hot tubs, sauna, a well-equipped fitness center, and a tennis court! What’s nearby: Stratton Mountain is filled with everything for the outdoor enthusiast! Just on the resort, you will find restaurants and apres-ski spots, shopping ranging from gear to fashion, a health center, pool, spa, and events. In the winter, there is skiing and snowboarding, snow tubing, snowmobiling, ice skating, snowcat rides, snowshoeing, and cross-country skiing. In the summer, there is mountain biking, hiking the Appalachian or Long Trail trails, kayaking, swimming, golf, fishing, tennis, and paddleboarding. Things to know: Free WiFi Full kitchen with a dishwasher Flat path to front door Elevator in building A sofabed in the living room provides an extra sleeping space The shared amenities may be closed due to local rules and regulations. We highly recommend that you check in with this facility directly to check the availability of the amenities Vermont Meals and Room Tax Number: MRT-11472019

Cozy Townhome with Shared Pool, W/D & Wood-Burning Fireplace

Stratton, VT, US
2 Bedrooms 8 Guests
Aug 25 - 27
$147 night

Nestled in the charming community of Styles Brook in Stratton, VT, this two-bedroom plus loft, two-and-a-half-bathroom townhouse offers a perfect blend of togetherness and privacy for families seeking a relaxing getaway. The spacious living and dining areas provide ample room to gather, while the fieldstone wood-burning fireplace and high-end stainless steel appliances in the kitchen add a touch of luxury to your stay. Situated in a peaceful corner of Styles Brook, you’ll enjoy easy access to the heated pool, perfect for unwinding after a day of adventure. Conveniently located on the Green Line resort shuttle route, you’ll have quick access to the slopes and village at Stratton ski resort, ensuring you can hit the trails or enjoy the amenities with ease. During the summer months, take a refreshing dip in the shared pool or explore the surrounding area with a variety of outdoor activities such as hiking, mountain biking, and kayaking. For a small fee, access the recreation and fitness center for a workout or relaxation session. Whether you’re seeking adventure or relaxation, this townhouse offers the perfect base for your Stratton getaway. With a range of amenities including a washer/dryer, balcony, and wood-burning fireplace, this condo provides all the comforts of home. Relax in the cozy living room, cook up a delicious meal in the fully equipped kitchen, or unwind on the balcony with a cup of coffee. Whether you’re planning a family ski trip or a summer retreat, this Stratton condo is the ideal choice for your next vacation. Book now and start planning your Vermont adventure! Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. 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. Vermont Meals and Room Tax Number: MRT-11472019

Stratton TreeTop condo with private hot tub, fireplace, decks & mountain view

Stratton, VT, US
3 Bedrooms 8 Guests
Aug 31 - Sep 2
$246 night

The year-round recreation of Stratton Mountain Resort is right outside your door at this four-story townhouse, where you’ll be a few steps from the slopes each snowy Vermont winter. Cap your days of adventure by soaking in the private hot tub, cozying up to the wood-burning fireplace, and taking in gorgeous views of the surrounding woods and mountains. This townhome sits at the end of a dead-end road, just over a mile from the main base area and the charming shops and restaurants of Stratton Village. A few steps away, you can meet up with the beginner-level 91 run to reach the Sun Bowl Base Lodge, the Solstice and Sunrise Express Lifts, and the Coca-Cola Tube Park down the hill. Each afternoon, hop on the intermediate-level Tree Top Way to ski all the way home. Whether you’re skiing in winter or golfing and mountain biking come summer, this is a wonderful place to begin and end each day. The heart of the home is the great room, a towering space with walls of windows, plush furnishings, and a fireplace that rises from floor to ceiling. Prepare meals in the well-equipped kitchen, sit down for family dinners at the dining room table, and gather for nightly movies on the smart TV. In the summer, enjoy decks off the great room and the primary suite, as well as a ground-floor patio that houses the hot tub. In the evenings, play board games, escape to the desk in the loft to log onto the WiFi, or simply retire to three bedrooms - each on its own floor and paired with a full bathroom for privacy. THINGS TO KNOW Vermont Meals and Room Tax Number: MRT-11472019

Mountainside resort condo, hot tub, gas fireplace, bus to slope, wifi, w/d

Stratton, VT, US
3 Bedrooms 8 Guests
Aug 25 - 27
$371 night

Nestled on the east side of Stratton Mountain Resort in the charming town of Stratton, VT, this light-filled condo offers the perfect retreat for outdoor enthusiasts and relaxation seekers alike. With 670 skiable acres, 97 trails, and the highest peak in Southern Vermont just a stone’s throw away, you’ll have endless opportunities for adventure right at your doorstep. During the winter months, take a leisurely stroll or hop on the convenient shuttle bus to reach the foot of the Tamarack lift or the main base area for a day of skiing and snowboarding. In the summer, tee off at the nearby Stratton Mountain Golf Course, located just two miles north, before unwinding on the balcony with a good book or mingling with fellow travelers at the recreation center across the street (access fee applies) where you can enjoy a friendly game of pickleball or tennis. The condo association has a shared hot tub available year round and it is located directly behind this unit! Guests have easy access to the Stratton Mountain Training and Fitness Center, managed by Stratton Mountain, offering indoor and saltwater pools, a gym, yoga classes, Peloton cycling, and more (additional fees may apply). Plus, a shared hot tub behind the unit provides a relaxing spot to soak year-round. For those seeking more excitement, the Coca Cola Tube Park for sledding is just a mile away, ensuring fun for all ages. Back at the condo, unwind in the cozy living space with a gas fireplace, enjoy a movie night with the DVD player and library, or whip up a delicious meal in the fully equipped kitchen. With amenities like a jetted tub, washer/dryer, and internet access, your stay is sure to be comfortable and convenient. Vermont Meals and Room Tax Number: MRT-11472019

Sunny Stratton Townhome ~ 1 Mi to Skiing!

Stratton, VT, US
3 Bedrooms 9 Guests
Aug 25 - 27
$334 night

Experience the idyllic beauty of Stratton, VT, and stay in this lovely 3-bedroom, 2.5-bathroom vacation rental! Nestled in the heart of the Green Mountains, this townhome is just minutes away from Stratton Mountain Resort, offering world-class skiing and snowboarding. Don't miss the nearby Pike Falls, a hidden gem known for its breathtaking beauty. After a day on the slopes, cozy up by the fireplace as you unwind with your group. This townhome is the perfect base for your Vermont adventure! -- THE PROPERTY -- Meals & Rooms Tax License No. MRT-11153470-001 | Mountain Shuttle | Free WiFi | 1,600 Sq Ft Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin Bunk Bed, Twin Bunk Bed w/ Twin Trundle | Additional Sleeping: Pack ‘n Play HOME FEATURES: Smart TVs, dining table, ceiling fans, board games, deck, heated floors KITCHEN: Refrigerator, stove/oven, coffee maker, microwave, dishwasher, dishware & flatware GENERAL: Washer & dryer, towels, linens, electric heating FAQ: No A/C, bears/wildlife in area ACCESSIBILITY: Multi-level townhome, exterior stairs to enter PARKING: Driveway (2 vehicles) -- THE LOCATION -- HIT THE SLOPES: Stratton Mountain Resort (1 mile), Stratton Sun Bowl Base Lodge (1 mile), Bromley Mountain Ski Resort (14 miles), Timber Creek Cross County Ski (14 miles), Mount Snow Ski & Snowboard School (14 miles), Okemo Mountain Resort (29 miles), Killington Resort (52 miles) ATTRACTIONS: Pikes Falls (3 miles), Green Mountain National Forest (5 miles), Jamaica State Park (12 miles), Lowell Lake State Park (15 miles), Lye Brook Falls (18 miles), Manchester Riverwalk (18 miles), Park-McCullough Historic Governor’s Mansion (40 miles), Bennington Museum (41 miles), Grafton Lakes State Park (58 miles) TEE TIME: Stratton Golf Course (2 miles), Manchester Country Club (17 miles), Mount Snow Golf Club (17 miles), The Golf Club at The Equinox (20 miles) AIRPORT: Rutland Southern Vermont Regional Airport (39 miles), Albany International 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: The property does not have air conditioning - NOTE: This multi-level townhome requires exterior stairs to enter and interior stairs to access all bedrooms and bathrooms - NOTE: Bears are frequently sighted in the neighborhood and the community has strict rules for trash disposal

Family-Friendly Stratton Gem Close to Slopes!

Stratton, VT, US
4 Bedrooms 13 Guests
Aug 25 - 27
$517 night

Skiers and adventurous families can appreciate the comfort and convenience of this Stratton vacation rental! The 4-bedroom, 3.5-bath townhouse offers an on-site shuttle service for Stratton Mountain Resort and is just a short drive from shopping and dining in Manchester. Plus, guests of all ages can enjoy a walkable location near the community pool and pickleball courts. After a fun-filled day, cook your crew a delicious meal in the fully equipped kitchen and watch a movie on the Smart TV. -- THE PROPERTY -- MRT-11153470-001 | Ski Shuttle On-Site | Deck w/ Fire Pit | Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Twin Bunk Bed, Twin/Full Bunk Bed | Bedroom 4: 2 Twin Bunk Beds | Additional Sleeping: Pack ‘n Play COMMUNITY AMENITIES: Pool (seasonal), pickleball court (pickleball racquets provided) MAIN FEATURES: Wood-burning fireplace, patio w/ dining area, 3 Smart TVs w/ cable, stereo, jetted tub, walk-in closet KITCHEN: Dishwasher, stove/oven, refrigerator, microwave, toaster, blender, coffee maker, Crockpot, dishware + flatware, cooking basics, garbage disposal, ice maker, water filter, complimentary spices + coffee, high chair, trash bags + paper towels GENERAL: Free WiFi (laptop friendly), central/electric heating, washer + dryer, laundry detergent, iron/board, towels/linens, complimentary toiletries, shampoo, hair dryer, hangers, board games, books, keyless entry FAQ: Stairs required for access, no A/C PARKING: Driveway (2 vehicles) -- THE LOCATION -- SKIING: Stratton Mountain Resort (1.2 miles), Bromley Mountain Ski Resort (12.5 miles), Timber Creek Cross Country Ski (13.7 miles), Magic Mountain Ski Area (14.4 miles) SHOPPING: Manchester Square Shopping Center (18.0 miles), Manchester Designer Outlets (18.3 miles) ALL-SEASON FUN: Pike Falls (3.1 miles), Prospect Rock Trail (17.1 miles), Lye Brook Falls Trail (18.2 miles), Mount Equinox Skyline Drive (23.8 miles) AIRPORTS: Rutland Southern Vermont Regional Airport (38.8 miles), Albany International Airport (76.9 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: The property requires stairs to access - NOTE: The seasonal pool is only open Memorial Day-Labor Day - NOTE: The property does not have air conditioning

Luxe 5,000 Sq Ft Retreat: 5 Mi to Stratton Resort

Jamaica, VT, US
4 Bedrooms 10 Guests
Aug 25 - 27
night

All-Ages Entertainment + Gaming Lounge | Dedicated Workspace | Sauna Craving adventure, indulgent comforts, and space to relax? Book your stay at this upscale 4-bed, 3.5-bath Jamaica vacation retreat. Wander through vibrant fall foliage in Green Mountain National Forest or carve fresh powder at Stratton. Afterward, return to unwind by the fire, soak in the private hot tub, or enjoy a game of billiards. This elegant haven pairs Vermont’s scenic charm with elevated New England luxury. -- THE PROPERTY -- MRT-11153470-001 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed - Bedroom 4: 4 twin beds - Additional Sleeping: 1 portable crib INDOOR LIVING - Smart TV, board games & books - Wood-burning stove - Gas fireplace, wood-burning fireplace - Dining table, work desk, monitor - Pool table, poker table, darts, Xbox - Spacious bedrooms, 5,200 sq ft OUTDOOR LIVING - Deck, gas grill (propane provided) - Outdoor seating, fire pit (firewood provided) - Screened-in porch, hot tub KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Drip/pod coffee maker (coffee provided), cream & sugar - Toaster, spices, blender - Cooking basics, dishware & flatware, trash bags & paper towels GENERAL - Central heating, window A/C units - Towels & linens, complimentary toiletries, hair dryer - Free WiFi - Keyless entry FAQ - 4 exterior security cameras (facing out) - Pet fee (paid pre-trip) ACCESSIBILITY - Multi-level home, step-free entry - All bedrooms on lower level - Stairs to access living areas & kitchen PARKING - Driveway (5 vehicles) - NEMA 14-50R EV charging station -- THE LOCATION -- - 5 miles to Stratton Mountain Resort - 12 miles to Bromley Mountain - 16 miles to Appalachian Trail access - 17 miles to Lye Brook Falls - 24 miles to Emerald Lake State Park - 76 miles to Albany 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 - Pet friendly w/ $75 fee (+ fees & taxes, dogs only, 1 pet max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This multi-level home offers step-free entry. While all bedrooms are on the lower level, stairs are required to access the living areas and kitchen - Your safety matters. This property features 4 exterior security cameras. Cameras 1 and 2 are on the front of the house facing the driveway. Camera 3 is on the front door facing the front entry. Camera 4 is on the back of the house facing the hot tub. The cameras are outward facing and do not look into interior spaces. The cameras record video when activated by motion

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Jamaica, VT, US
5 Bedrooms 12 Guests
Oct 31 - Nov 2
$337 night

Escape to this spacious and expansive five-bedroom house nestled in a serene wooded setting in Jamaica, VT and just 15-minutes from Stratton. Perfectly located within a short driving distance to other popular ski resorts such as Bromley, Mount Snow, and Magic, this home is an ideal retreat for outdoor enthusiasts and nature lovers alike. The spacious main level living area boasts a beautifully updated kitchen, a charming dining area, a stone fireplace with a vaulted ceiling, and two sets of glass doors that lead out to a large outdoor deck, perfect for enjoying the fresh mountain air. With three bedrooms on the first floor, including one with an en-suite bathroom, and two additional bedrooms upstairs with a full bath, this home offers ample sleeping accommodations for families or groups of friends. In addition to the inviting main living space, this home features a second bright living area, a 3rd bathroom, and a spacious loft area containing a bumper pool table, games and puzzles, providing plenty of room for relaxation and entertainment. A mudroom is equipped to store all your outdoor gear and ski equipment. Explore nearby attractions such as the Viking Nordic Center, Jamaica State Park, Coca Cola Tube Park, Angel Falls Trailhead, and Ball Mountain Reservoir, all just a short distance away. After a day of outdoor activities, return to the house to unwind by the wood-burning fireplace, gather around the firepit on the deck, or enjoy a meal prepared in the fully equipped kitchen with modern amenities. A wonderful winter ski getaway, this dog-friendly house offers a comfortable and convenient home base for your Jamaica vacation. Book your stay now and experience the beauty and tranquility of Vermont’s countryside. Vermont Meals and Room Tax Number: MRT-11472019

Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn

Peru, VT, US
3 Bedrooms 8 Guests
Aug 25 - 28
$334 night

Sun or snow, this renovated vacation rental condo in Peru, Vermont is the perfect getaway! Located at Bromley Mountain Ski Resort, the 3-bedroom, 2-bathroom home with interior updates includes access to a community pool, tennis courts, a fitness center, and more. Spend cold winter nights gathered around the fireplace and warm summer evenings admiring the garden views from the patio. Take advantage of all-season activities like skiing, an adventure park, hiking, and shopping in nearby Manchester! -- THE PROPERTY -- MRT-11153470-001 | Furnished Patio | Community Amenities Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: 2 Twin/Twin Bunk Beds COMMUNITY AMENITIES: Pool, tennis courts, playground, fitness center, clubhouse KITCHEN: Fully equipped, coffeemaker, dishware, flatware, tea kettle, 7-person table, updated backsplash INDOOR LIVING: 58" Smart TV, TVs in all bedrooms, charging stations & Bluetooth speakers in all bedrooms, fireplace, en-suite bathroom, shower/tub combos GENERAL: Linens/towels, free WiFi, garden views, central heating, updated lighting, updated tile floors in bathroom FAQ: No A/C, pet fee (paid pre-trip) PARKING: Parking lot (1 vehicle), 2 overflow parking lots -- THE LOCATION -- SKI RESORTS: Bromley Mountain Ski Resort (on-site), Magic Mountain Ski Area (11.2 miles), Stratton Mountain (15.1 miles), Okemo Mountain Resort (26.2 miles) OUTDOOR RECREATION: Bromley Mountain Adventure Park (on-site), Long Trail/Appalachian Trail (2.2 miles), Hapgood Pond (5.0 miles), Lowell Lake State Park (11.7 miles), Green Mountain National Forest (25.1 miles) MANCHESTER, VERMONT (9.3 miles): Manchester Designer Outlets, Hildene - The Lincoln Family Home, The Reluctant Panther Inn and Restaurant, Raven's Den Steakhouse and Taproom, Copper Grouse AIRPORT: Albany International Airport (66.5 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 - Pet friendly w/ $150 fee (+ fees & taxes) - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property does not have air conditioning Licence number: MRT-11083404

Tranquil house w/ pond, 3-hole golf course, sandy beach, bbq, firepit, & trails

Londonderry, VT, US
3 Bedrooms 6 Guests
Aug 31 - Sep 2
$216 night

Escape to this stunning two-story house nestled on 40 acres in Londonderry, VT, where adventure and relaxation await. With three spacious bedrooms and 2.5 bathrooms, this home is perfect for families or groups seeking a memorable getaway. Step outside onto the expansive deck with your morning coffee and soak in the serene views of your private pond, complete with a sandy beach for summer water activities. The property also features a private 3-hole golf course, making it an ideal retreat for golf enthusiasts. Enjoy the great outdoors with marked and groomed trails right on the property, perfect for hiking, snowshoeing, or sledding down the hill in winter. The West River Trail, a scenic 36-mile all-season trail, is less than a mile away, offering opportunities for biking, walking, and cross-country skiing. After a day of adventure, gather around the firepit for cozy evenings under the stars. Inside, the well-equipped kitchen and dining area provide all the comforts of home, while the gas fireplace adds warmth and ambiance. With amenities like a washer/dryer, partial air conditioning, and free WiFi, your stay will be both comfortable and convenient. Two of the bedrooms are located on the first floor, offering easy access to the enclosed outdoor shower. Whether you’re looking to explore nearby attractions like Magic Mountain, Viking Nordic Center, or Lowell Lake State Park, or simply unwind in the tranquility of your own private oasis, this Londonderry home is the perfect destination for your next vacation. Book your stay today and create lasting memories in this beautiful Vermont retreat! Town of Londonderry STR License # is 26-01-163 Vermont Meals and Room Tax Number: MRT-11472019

Tree-lined lodge with deck, fireplaces, porch, game room, & fast WiFi

Peru, VT, US
3 Bedrooms 8 Guests
Sep 14 - 16
$340 night

With Vermont’s year-round wonders readily available in every direction, this lofty lodge in Peru provides you with the space you want and need to relax. At this quiet, tree-lined home, you’ll have a private deck, a screened porch, and a fun-filled, renovated game room to fill your vacation days. The interior encompasses three spacious levels, with the main living area on the middle floor. It’s an airy space with natural wood and brick, offering towering ceilings, exposed crossbeams, and an impressive wood-burning fireplace with a floor-to-ceiling hearth. Kick back on the sectional and watch shows on the 50-inch smart TV with a soundbar and Sonos speakers. Enjoy stainless steel appliances in the well-appointed kitchen. Perch at the breakfast bar, with a wet bar at one end, then gather for memorable meals at the dining room table. Just beyond the living room is a screened porch with another table for meals or board games and an open deck overlooking the yard. Run around with your kids outside, or head downstairs to the renovated game room to watch a Netflix movie, build a fire, or play foosball and air hockey. At night, as the day’s clothes spin in the washer/dryer, you’ll find beds on each of the three floors. There’s a primary bedroom suite on the main level, two bedrooms downstairs, and a great sleeping space beneath the rafters upstairs. Nest thermostats and high-speed WiFi add convenience during your stay. Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. Streaming services are available with guests’ own account(s). This vacation rental is not equipped with air-conditioning. 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.

Manchester Center Retreat w/ Mtn View, Near Skiing

Manchester, VT, US
2 Bedrooms 6 Guests
Sep 9 - 11
$181 night

Enjoy a relaxing Manchester Center getaway at this 2-bedroom, 1-bath vacation rental apartment. With views of the Green Mountains and plenty of recreation available within the national forest and Bromley Mountain Ski Resort—this home is a true four-season getaway! After a day of skiing or hiking, cozy up in front of the TV or head outside for some cocktails. In need of more exploring? Check out Abraham Lincoln’s family home or head into Manchester Center for some dining and shopping. -- THE PROPERTY -- MRT-11153470-001 | Private Yard w/ Seating | Pets Welcome w/ Fee | Gas Grill Bedroom 1: 2 Queen Beds | Bedroom 2: 2 Twin Beds | Living Room: Queen Sofa Bed KITCHEN: Fully equipped, kitchen island, coffee maker, dishware & flatware INDOOR LIVING: Flat-screen cable TV, dining table, ample seating GENERAL: Free WiFi, brand new washer & dryer, linens & towels, central heating, window A/C units (available in the summer), pet fee (paid pre-trip) FAQ: Community pool unavailable PARKING: Driveway (2 vehicles) -- THE LOCATION -- GREEN MOUNTAIN NATIONAL FOREST (surrounding): Hiking, fishing, cross-country skiing, snowmobiling, horse riding, mountain biking, etc SKI RESORTS: Bromley Mountain Ski Resort (5.7 miles), Stratton Mountain Resort (14.8 miles) ATTRACTIONS: Manchester Center (2.0 miles), American Museum of Fly Fishing (2.8 miles), Lincoln Family Home (4.9 miles), Vermont Summer Festival Horse Show (5.2 miles) AIRPORT: Albany International Airport (62.8 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 - Dog friendly w. $100 fee (+ fees & taxes, maximum 1 dog allowed). Reach out to Evolve upon booking to add this fee if you are bringing a pet - No events, parties or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - The community pool is currently not available. There are lovely swimming lakes available within 10 minutes of the property - The A/C is available in the summer Licence number: MRT-10867224

Peaceful mountain home near skiing, hiking, mtn biking & more

Jamaica, VT, US
3 Bedrooms 8 Guests
Aug 25 - 27
$185 night

Escape to the serene beauty of Jamaica, Vermont, where adventure and relaxation await in this charming house. Perfectly situated just a short drive from Bromley and Stratton Mt, this property offers easy access to a plethora of all season outdoor activities. Enjoy thrilling days at Bromley’s water park, scenic chair lift, alpine slide and winter skiing or hit the slopes at Stratton (Ikon Pass) for skiing, snowboarding, summer concerts, gondola rides and mountain biking. With Okemo and Mt. Snow (Epic pass) also within a short drive, you’ll have endless options for winter sports and summer fun. This cozy home is designed for comfort and convenience, featuring a wood-burning fireplace, partial seasonal AC, and a well-equipped kitchen with modern appliances. Gather on the deck for evening relaxation, or enjoy family game nights with the provided board games. With ample sleeping arrangements, including 2 king beds and 2 queen beds everyone will have a restful night after a day of adventure. Whether you’re looking to hike through stunning autumn foliage, swim at Dorset Quarry, or explore local dining and shopping, this vacation rental is your gateway to Vermont’s natural wonders. Book your stay today and create unforgettable memories in this idyllic retreat! Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. -No Pets allowed -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 events, parties or large gatherings -No smoking is permitted anywhere on the premises. Vermont Meals and Room Tax Number: MRT-11472019

Award-Winning Log Cabin, Top 5 in New England!

Londonderry, VT, US
2 Bedrooms 4 Guests
Aug 25 - 27
$230 night

Your summer adventures begin at ‘West River Lodge,’ a cozy 2-bedroom, 1-bath vacation rental log cabin in the Southern Vermont woods. With 3.5 acres of private woodlands and a great location minutes from many summer activities (Vermont Summer Festival, hiking, fishing, biking) and the town of Londonderry, this cabin is the perfect home base for a summer getaway! In the winter, visit for fantastic skiing and snowboarding at nearby resorts like Stratton Mountain, Bromley Mountain, and more. -- THE PROPERTY -- MRT-11153470-001 | Free WiFi | Pets Welcome | Back Deck | Fire Pit Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds OUTDOOR LIVING: 3.5 acres, peaceful surroundings, gas grill, fire pit (seasonal) INDOOR LIVING: Flat-screen TV with Netflix, wood fireplace, dining table, handicap accessible design KITCHEN: Fully equipped, Keurig coffeemaker, tea kettle, pots and pans, catering service available upon request (paid separately) GENERAL: 1,036 Sq Ft, washer/dryer, linens/towels, hairdryer, cellphone service FAQ: Fire pit available seasonally, 1 step to enter, no A/C, pet fee (paid pre-trip) PARKING: Driveway (4 vehicles) -- THE LOCATION -- SUMMER ACTIVITIES: Wanderlust Yoga Festival (11.8 miles, June 20-23), Bromley Mountain-Adventure Park (7.2 miles), Lowell Lake State Park (4.3 miles), Gale Meadows Pond (7.3 miles), West River Trail (8.9 miles), Ball Mountain Lake (11.7 miles), Jamaica State Park (11.9 miles), Hamilton Falls (13.3 miles), Prospect Rock Trail (13.8 miles), Lye Brook Falls Trail (14.8 miles), Manchester Riverwalk (15.0 miles), Orvis Fly Fishing School (15.9 miles), Bourn Pond (24.7 miles) SKI RESORTS/WINTER ADVENTURES: Stratton Mountain (11.8 miles), Bromley Mountain (7.2 miles), Okemo Mountain (17.2 miles), Magic Mountain (3.7 miles), Viking Nordic Center (2.2 miles) DINING/SHOPPING: Londonderry (0.9 miles), Manchester (16.5 miles), Dorset (19.5 miles), Townshend (19.8 miles), Somerset (46.5 miles) AIRPORT: Albany International Airport (75.1 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 - Pet friendly with $25 fee (+ fees & taxes, 2 pets max) - No parties, events or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This property requires 1 step to enter - Catering available by a third-party vendor upon request. This includes options for a catered breakfast, lunch, or special dinner with costs paid directly to the catering service. Please reach out if you would like to be connected to the caterer - While there is no air conditioning, fans are provided at the property - This property was recently named one of the top 5 'Coziest Cabins in New England'

Vacation Rentals in Winhall by Amenities & Features

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Vacation Rentals Near Winhall

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