Large group vacation rentals in St Michaels, MD

This 1-bedroom home is jam-packed with amenities & has EVERYTHING you need for an amazing vacation in St. Michaels, MD! • Prime Downtown Location: Walk to Dining, Shopping, & Waterfront Area! • Stocked Kitchen w/ Coffee Bar • Gas Fireplace • Plush Sofa & Smart TV • King Bedroom w/ Smart TV, Sitting Area • Ensuite Bathroom w/ Marble Shower • Family/Kid Friendly • Designated Parking (2 Spots) • High Speed WIFI • Washer & Dryer Step into Flat 207, a bright and stylish 1-bedroom, 1.5-bath flat designed for relaxation and comfort. Perfect for couples or solo travelers, it comfortably sleeps up to 4 guests. Located on the second floor, you’ll enjoy peace, privacy, and sun-filled rooms that set the tone for a serene escape. The open-concept living area invites you to relax with comfortable seating, a cozy gas fireplace, and tasteful modern décor. Whip up meals in the fully stocked kitchen, enjoy a glass of wine at the dining table, or head out to explore the local downtown scene. When you return, the spacious bedroom features a king bed with premium linens, while the sleek bathroom boasts a spa-like marble walk-in shower. Located just steps from the harbor, shops, and award-winning restaurants, this bright and modern flat offers both comfort and convenience. Whether you’re here for a romantic getaway, a wedding weekend, or a peaceful escape on the Eastern Shore, you’ll love coming home to this stylish space. MAIN SPACES OF THE HOME: – 1 BEDROOM & 1.5 BATHROOMS – BEDROOM 1: * King-sized Bed * Smart TV * Nightstand & Lamps * Ensuite Bathroom – 1.5 BATHROOMS – * Ensuite Bathroom with Walk-in Shower * Half Bathroom – CHEF’S KITCHEN – * Fully Stocked * High-end Stainless Appliances * Ample Cabinetry & Cooking Space – LIVING ROOM – * Smart TV * Pull-Out Sofa * Indoor Fireplace * Open Floor Plan The guest has access to the entire home minus the locked cleaners’ closet. By Car: Renting a car is a convenient option to explore the area at your own pace. Having a car makes it easy to visit the many shopping centers, restaurants, and other points of interest in the area. Rideshare Services: Services like Uber and Lyft are readily available in the area, providing a convenient alternative to driving. Simply book a ride through the app, and you’ll be on your way to your destination in no time. Check-in is at 4pm Check-out is at 10am - No pets allowed. - Stays of 28 days or more may incur an additional cleaning fee - No parties allowed—violations may result in immediate termination of the stay. We aim to maintain a respectful environment for our neighbors. - An exterior camera is installed solely to monitor our cleaning team for quality and security purposes. - Parking is available for 2 vehicles in the driveway. Please note that street parking is not allowed. - If you’re interested in a long-term stay, please reach out to inquire about availability - Guests must be 21 years or older to book this property. GUEST VERIFICATION: To help ensure a smooth and secure stay for all guests, the primary guest listed on the reservation may be asked to complete a quick verification process within 48 hours of booking, depending on the platform used to book the reservation. Prior to check-in, guests may also be asked to sign a Rental Agreement that includes agreeing to our rental terms and conditions and, on certain booking platforms, providing a valid government-issued ID and matching credit card before arrival. Included with your booking is our damage waiver coverage, which helps protect against accidental, self-reported damage during your stay when reported prior to check-out.

Cottage in Center of Historic St. Michaels This lovely in-town cottage is close to all the amenities and charms of historic St. Michaels. Enjoy outstanding restaurants and boutiques, ice cream parlors, coffee shops, art galleries and more, all within a few steps of this beautiful home! Try the local winery, distillery, and brewery for tastings of hand-crafted spirits (no driving required!). Head toward the Miles River waterfront for freshly caught and steamed crabs. If you want to venture farther, within just a couple of blocks you can easily rent bikes, kayaks, or paddleboards and let your adventurous side soar. Offering modern conveniences in a quintessential Eastern Shore village, Carpenter Alley Cottage is a fabulous place to stay! PROPERTY FEATURES: Pet Policy: This is a pet friendly rental. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: Bunk Bed - Single over Single - 1 / Queen - 1 / Queen - 1 / Queen - 1 /

Begin your day at Riverview Retreat with a beautiful sunrise and be amazed with a stunning sky at sunset. As soon as you enter this charming cottage you are greeted with wide open vistas of the Miles River from the foyer, living room, sun room, kitchen and dining room. Freshly painted and appointed with modern and comfortable furnishings, bedding and a well-stocked gourmet kitchen, this three-bedroom two and a half bath home is sure to please. Located close (75ft) to the water’s edge, where you can fish or crab from the private dock. Crab cages are available for your use as well as 2 kayaks, 2 paddle boards, cornhole boards, and 2 adult bikes to mosey into St. Michaels for ice cream or a little shopping. Or simply relax in the Adirondacks and enjoy the sailboat races and wildlife that frequent, including osprey, turtles, rays and even the occasional pod of dolphin that make their way up the Miles River. St Michaels is a 15-minute walk or less than 5 minutes by bike with all the conveniences, including shopping, restaurants, wineries, the Chesapeake Bay Marine Museum and more! Talbot County STR License #ST-910

Fantastic Family Compound Just 1/2 Mile to Historic District! Located just on the outskirts of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway. The lovingly restored farmhouse has a brand new gourmet kitchen, five bedrooms, a cozy den, and a screened porch with a gas fireplace to warm you on those breezy summers or early fall mornings. There is plenty of room for everyone to spread out, play games, or enjoy coffee and plan the day while overlooking the formal garden. The grounds are lush with mature landscaping, plenty of privacy, centuries-old shade trees, and room to roam for the little ones. Enjoy the new gazebo: a perfect backdrop to capture some treasured family photos! The newly restored barn supplies endless opportunities for your kids or kids-at-heart with game tables, air hockey, and foosball. Work off the crab cakes and ice cream with the Vectra gym and rowing equipment! The pool is flanked by a pool house complete with a changing area and two full baths for showering, in addition to a kitchenette for your snacks and favorite beverages. The hot tub and pickle ball court are open year round for your enjoyment as well. The deep-water slip has easy access to the Miles River and St. Michaels harbor. Kayaks are included with this property to explore the smaller creeks and nature-watch on a peaceful morning. Like a good Captain, the owner has taken meticulous care to ensure your enjoyment of this home. Guests who have previously stayed here will appreciate the continual upgrades, including new pool furniture, restored steps in the barn and other improvements. This home offers something for everyone! Talbot County STR License ST-26-25 PROPERTY FEATURES: Waterfront: Long Haul Creek Dock: 100ft L-shaped dock with 6ft MLW, water and 30 amp electricity available for guest use. The owner keeps a sailboat at the long end of dock. Interior slips are available for guest use. Pickleball Court: Available for guest use. Water Toys: 1 tandem kayak, 2 medium-sized kayaks (175lbs or less) and 1 stand up paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Hot Tub: Open year round and available for guest use. Grill: Propane grill. Propane is provided. Barn: The ground floor of the barn is not available for guest use between October and April. Pet Policy: Pets are not permitted. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: Upon request an ESVR representative greeting at your arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.

1/2 Mile to Historic District, Pickleball Court, 3 Private Suites! Step into this idyllic, uniquely Eastern Shore Nanticoke mid- century home, perfect for friends and family, especially for multiple couples looking to be a short drive into the historic town of St. Michael’s . This spacious 3-bedroom, 3.5-bathroom home was renovated top-to-bottom in 2022 with an open-design floor plan, formal dining room, and large entertainment spaces. Extra large windows through-out provide wonderful views open field farmland . The kitchen boasts commercial-grade appliances, granite countertops, and a center butcher block island to take entertaining to the next level. The outdoor space is the perfect place to relax and entertain, with an open air pavilion complete with lounge seating, large dining table, propane grill, outdoor shower , a built-in heated swimming pool and hot tub, as well as a propane fire pit- perfect for late night star gazing . Bikes are conveniently stored in the garden shed. Don’t miss out on the opportunity to celebrate in this luxurious yet easygoing property. Talbot County STR License STN-26-21 PROPERTY FEATURES: Pool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Heat is available for an additional fee. Please contact us if you want to add this option. Hot Tub: Hot tub is available for guest use. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

Let go of your cares and enjoy the respite of this Covey Creek waterfront home. Let the kids play in the fenced-in yard and enjoy an easy getaway close to historic St. Michaels. Boasting two living areas, four spacious bedrooms, and a light-filled sunroom, this is a place for relaxing! You’ll certainly be comfortable while vacationing with family and/or friends. The waterside picnic table is perfect for crab feasts and alfresco lunches. Use the kayaks and paddleboards to explore the creek and beyond. The Landing provides a low-key, easy vacation experience on the Shore! Talbot County License #ST-236-HIN-2019

Talbot County STR License STN-22-27 This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interior and features a separate dining room. A foodie’s dream, this well-equipped recently updated kitchen is space efficient. Retreat to the comfortably sized main bedroom that comes complete with spacious closets. Out back, you’ll find the ultimate rural retreat, equipped with a large outdoor deck, private pool and hot tub. The perfect location for outdoor fun. Your search for the finest vacation living is over. Nestled in a sought-after Talbot County neighborhood. Don’t miss out on relaxing at this fabulous home. Book your getaway today.

No expense spared! The impressive 6BR, 5.5BA St. Michaels waterfront getaway has recently been remodeled throughout with your comfort in mind. The open floor plan features a modern interior and provides large entertainment spaces. No expense was spared in this chef-inspired kitchen that comes equipped with dual ovens, wine fridge and island with butcher block countertop. The home boasts a master suite on both the first and second floors, each with a luxury ensuite bathroom and waterfront view. The 10-acre property has a resort-like backyard complete with a shady pergola, picnic tables, built-in swimming pool, and rolling green lawn. The westward facing screened porch provides a great spot for enjoying a morning cup of coffee or an evening cocktail with the sunset. Perfectly positioned close to downtown St. Michaels. Discover all the perks of this extraordinary property. A rare vacation opportunity for a large family. Early booking is recommended. Talbot County STR License STN-26-37 PROPERTY FEATURES: Waterfront: Rolles Creek with 300ft of shoreline. Dock: 75ft private dock. Water and electricity are available for guest use. Water Toys: 1 Kayak, 1 Canoe and 1 Paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Land Toys: 3 bicycles are available for guest use. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: Upon request an ESVR representative greeting at your arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.

Dragonfly Cove offers an idyllic retreat just a seven minute drive from the heart of St. Michaels, Maryland. This charming waterfront home boasts a perfect blend of comfort and elegance, making it an ideal getaway for families and friends alike. Upon entering, you’re greeted by an inviting open-concept living space adorned with chic decor and large windows that flood the area with natural light. Multiple seating areas provide the perfect opportunity to unwind after a day of exploration — whether you are reading a book, enjoying the views, or relaxing in front of the smart TV. The fully equipped kitchen is a culinary haven, complete with modern appliances, cookware galore, granite countertops, and ample storage space. Whether you’re whipping up a quick meal or hosting an intimate dinner party, this space has everything you need. Adjacent to the kitchen, you’ll find a dining area that seats up to eight, providing the perfect spot to enjoy meals together. The main bedroom is a serene sanctuary, featuring a luxurious king-sized bed with a comfy Purple brand mattress, a private en-suite bathroom, a smart TV, and a private deck with rocking chairs and water views. The second bedroom offers two twin beds (also with Purple brand mattresses), blackout shades, and shares a spacious hall bathroom, ensuring privacy and comfort for all guests. Dragonfly Cove also offers a range of premium amenities, including a pool with a tanning ledge and loungers (and available heat), a spacious spa, and a private dock for crabbing, fishing, and other water adventures. Guests will enjoy exploring the cove and beyond in the provided kayaks and paddle board, have fun play lawn games by the bay, and relax watching the birds from multiple outdoor seating and dining areas, including a screened porch. Guests will also appreciate the convenience of free high speed Wi-Fi, a designated desk/work area, and laundry facilities. St. Michaels is a delightful town brimming with attractions and activities. Start your day with a visit to the Chesapeake Bay Maritime Museum in St. Michaels, where you can learn about the town’s rich maritime history. For a taste of local culture, head to the St. Michaels Wine Festival, held annually in October, featuring award-winning wines and local cuisine. The nearby Chesapeake Bay is perfect for fishing, crabbing, and sailing, offering endless opportunities for adventure. The Crab Claw Restaurant, adjacent to the Chesapeake Bay Maritime Museum is a must-visit, serving authentic fresh Maryland seafood and stunning bay views. There are numerous other dining options in St. Michaels from gourmet to casual — to name just a few of our favorites: Ruse, Limoncello, Ava’s, Bistro St. Michaels, Corah’s Corner, STARS, The Galley, Theo’s, and many more. If you’re looking for a delicious takeaway meal, try these gourmet markets: The Village Shoppe, Eat Sprout, or Simpatico. Craving ice cream or sweets? Stop by JoJo’s, Justine’s Ice Cream, Arabia Chocolate, or Olde Town Candy company. If you’d like to venture out of Saint Michael’s, make the short drive to Tilghman Island to try breakfast or lunch at Two If By Sea, or into Easton for a multitude of additional options. Whether you’re seeking relaxation or adventure, Dragonfly Cove provides the perfect setting for your next getaway. Book your stay today and experience the best of the Eastern Shore of Maryland. Talbot County STR License STN-23-38 PROPERTY FEATURES: Waterfront: Harris Creek. 375 feet of shoreline. Dock: Brand new dock available for guest use. Water Toys: 3 kayaks and 1 paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Brand new pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Hot Tub: Brand new hot tub available for guest use. Land Toys: Assortment of lawn toys/games are available for guest use. Grill: Propane grill. Propane is provided. WiFi: Reliably fast (good for 6-8 people or up to 10 devices). BED SIZES: King - 1 / Single Bed - Twin Sized - 2

Pets Welcome w/ Fee | 5 Mi to St. Michaels | Go Kayaking Experience classic Eastern Shore living at this 4-bedroom, 2.5-bath Bozman home — ideal for families, friends, and anyone craving a peaceful escape. The vacation rental boasts a fishing dock, a hot tub to unwind in the evenings, and acres of lawn where kids and pets can roam. Enjoy the spacious custom kitchen, gathering spaces, and thoughtful touches like shelves stocked with games. Head to Tilghman Island for even more adventure! -- THE PROPERTY -- STN-24-6 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 king bed - Bedroom 3: 2 full beds - Bedroom 4: 1 twin daybed w/ 1 twin trundle - Additional Sleeping: 1 portable crib OUTDOOR LIVING - Hot tub, 20'x40' swimming pool (heated w/ fee) - Private yard (unfenced) - Creek access w/ fishing dock - Kayaks & paddleboard - Furnished deck w/ Solo Stove fire pit - Charcoal grill, bicycles - Covered front porch w/ seating INDOOR LIVING - Multiple Smart TVs w/ cable - Nintendo console - Wood-burning fireplace - 2 dining tables & breakfast bar - Board games, toys & books KITCHEN  - Stove/oven, refrigerator, dishwasher - Microwave, toaster, blender - Drip coffee maker & Nespresso Vertuo (bring your own coffee) - Ice maker, cooking basics, spices - Dishware/flatware - Trash bags & paper towels GENERAL  - Free WiFi - Washer & dryer (detergent provided) - Central A/C & heating, ceiling fans - Linens/towels, complimentary toiletries - Iron/board, hair dryer - Keyless entry FAQ - Pet fee (paid pre-trip) - Optional nightly pool heat fee (paid pre-trip, applied to entire stay) ACCESSIBILITY - 2-story home, 5 steps to enter - All bedrooms & full bathrooms on 2nd floor PARKING - Driveway (4 vehicles) - RV/trailer parking allowed on-site (240V outlet in garage; no hookups) - Tesla-compatible EV charger (24 Amp) -- THE LOCATION -- - 3-acre plot on Harris Creek: fishing, crabbing, canoeing, paddleboarding & kayaking - 5 miles to Chesapeake Bay Maritime Museum, waterfront dining & local shops - 14 miles to Dogwood Harbor - 15 miles to Phillips Wharf Environmental Center - 76 miles to Baltimore/Washington 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/ $50 fee (+ fees & taxes) - 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 requires 5 steps to enter; all bedrooms and full bathrooms are located on the 2nd floor - There is an optional pool heat fee of $50/night (+ fees & taxes, paid pre-trip, applied to entire stay) - Due to the clay-heavy soil and water retention in the area, mosquitoes can be more common after rain. You are encouraged to bring bug spray or citronella products for added comfort outdoors

A Tranquil Contemporary St. Michaels Waterfront Cottage featuring a separate 1st floor newly renovated garage apartment with its own kitchen. This 6BR, 4.5 BA vacation paradise is conveniently located between the charming towns of St Michaels and Easton, Bayside The Point is just a stone’s throw away from numerous shops, boutiques, and dining experiences to please the entire family. The house is nestled among trees at the far end of a private road and provides a truly safe, peaceful and tranquil haven. With only birdsong and the gentle rustling of trees in the cool southerly breeze, you can be assured of a completely restful and private vacation. Set on a point, the aptly named Solitude Creek wraps around this lovely house, affording you water views from every room. The master suite benefits from a private deck where you can begin your day with freshly brewed coffee and a soul-warming sunrise. A large south-facing deck with ample outside dining area will enable you to make the most of outside living on your well-earned break. Take a dip in the pool, catch crabs and fish off the dock, relax by the firepit or just enjoy a delicious BBQ. This house is well-appointed, with a clean and modern feel. Glass doors line the whole back of the house, providing beautiful, uninterrupted views down Solitude Creek. The resident Ospreys are normally just a few feet offshore; these magnificent birds coupled with the shimmering waters will provide you with hours of viewing pleasure. Talbot County STR License STN-23-37 PROPERTY FEATURES: Waterfront: Solitude Creek Dock: 750 feet of shoreline with 80 ft of private dock with 4.5 ft MLW Guest House: 1st floor newly renovated garage apartment with its own kitchen. Water Toys: 2 kayaks, 1 canoe, 2 paddle boards and crabbing gear is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 600 sq ft private swimming pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Grill: Propane grill. Propane is provided. Hot Tub: 6 person hot tub is available for guest use. Firepit: Wood provided. Pet Policy: This is a pet friendly property. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Queen - 1 / Queen - 1 / Double Bed - 1 / Single Bed - Twin Sized - 2 / Single Bed - Twin Sized - 1

Lovely and serene-the perfect spot to nurture your soul! This 5,000 square foot, 5-bedroom, 5-bathroom waterfront was designed with your comfort in mind, the open floor plan features a modern interior and incorporates a separate dining room, flow-through living area and a generous bonus suite. The appliances enhance this gorgeous recently remodeled kitchen, equipped with quartz countertops and sprawling island. Drift off to sleep each night in the opulent main suite that comes complete with an ensuite bathroom, private balcony, and water views. The wonderfully secluded backyard boasts a patio dining space and a 18’x39’ built-in swimming pool with tanning ledge. You will love this waterfront vacation home! Well placed in a sought-after Talbot County neighborhood. This unique home will book fast! Talbot County STR License STRN-22-36 PROPERTY FEATURES: Waterfront: Leeds Creek Dock: Private dock with bench and beautiful views. Guests are not permitted to tie a boat to the dock. Water Toys: 2 kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Brand new 18’x39’ built-in swimming pool with tanning ledge. Guests swim in pool at their own risk. Pickleball Court: Pickleball court for guest use. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: Available for guest use. BED SIZES: King - 1 / King - 1 / Queen - 1 / Queen - 2 / Bunk Bed - Single over Single - 1 / Sleep Sofa - Queen - 1 /

Nestled on the serene waterfront of Leeds Landing, this expansive single-story retreat is the perfect haven for families and friends. Boasting a prime location, this home sits on a tranquil 2+ acre lot on Leeds Creek, offering stunning views and direct access to the Miles River. The deep water dock (MLW 4’) makes it easy to enjoy fishing, crabbing, or boating adventures. Inside, the spacious living area is designed with comfort in mind, featuring five cozy bedrooms and three full bathrooms, comfortably accommodating up to ten guests. The master suite offers a luxurious king bed, while additional bedrooms include a queen bed, a crib, two bunk beds, and a twin bed, ensuring everyone has a restful place to sleep. The sunroom and screened porch provide breathtaking views of the backyard pool and waterside fire pit, perfect for relaxing or enjoying evening meals. The fully equipped kitchen has everything you need to prepare a meal, and the dining area seats all guests comfortably. The outdoor dining area, complete with a gas grill and outdoor seating, is ideal for barbecues and al fresco dining. For those who enjoy water activities, a canoe is provided, and a private pool is available for a refreshing dip. Just a short distance away, explore the charming town of Easton, MD, where you can visit the Easton Historic District, enjoy dining at local favorites like The Easton Crabhouse, or take a stroll along the scenic Miles River. Whether you’re seeking adventure or relaxation, this waterfront retreat promises an unforgettable getaway. Book your stay today and experience the perfect blend of comfort, convenience, and natural beauty. Talbot County License ST-969-LEE PROPERTY FEATURES: Waterfront: Leeds Creek Dock: 100ft with 4ft MLW, water and electricity. Water Toys: 1 canoe is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Firepit: Firewood is not provided. Grill: Propane grill. Propane is provided. Pet Friendly: Owner will consider pets, call reservations at 443.664.4039 to inquire. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Crib - 1 / Queen - 1 / Queen - 1 / Queen - 1 / Bunk Bed - Single over Single - 2 / Single Bed - Twin Sized - 1 /

One Of A Kind! Tranquil and timeless, Fairview is among the great historic estates of Talbot County. Offering a total of 6 bedrooms, 4 full baths and 2 half baths, the home and property provide ultimate peace and privacy. The waterfront estate is located on the Eastern Shore and sits at the end of a peninsula on the Miles River, a 12.9-mile-long tributary of the Chesapeake Bay, and is equidistant to the towns of Easton and St. Michaels. The estate’s picturesque grounds encompass 74 acres of private parkland, 19th-century formal gardens, and 1,500 feet of shoreline with a private beach. With 3 private golf holes, an 20’ x 47’ pool, basketball court with hoop, tennis court, a gym, and 50 acres of backyard, this vacation experience offers excitement for the whole family. Fairview Estate with its serene and private setting offers a rare rental opportunity to enjoy the best that the Eastern Shore has to offer. Talbot County STR License STN-26-31 PROPERTY FEATURES: Waterfront: Miles River with 1500’ of shoreline. Dock: Floating dock. Guests are not permitted to tie a boat to the dock. Water Toys: 1 double and 1 single kayak are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: 47’ x 20’ private pool. Swimming pools are open from May 15 - October 15. Heat is available for an additional fee. Please contact us if you want to add this option. Pool House: Pool house with bathroom and shower available for guest use. Private Beach: Private beach with floating dock and water toys available for guest use. Grill: 2 propane grills. Propane is provided. Golf Course: Three hole (Par 3) golf course and practice area. Bring your own clubs. There will be practice balls available for guest use. Exercise Room: Exercise room available for guest use. Fire Pit: Available for guest use. Land Toys: 8 bicycles are available for guest use. Pet Friendly: This is a pet friendly rental. WiFi: Included for guest use. THIS IS A LUXURY RENTAL: Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include: An ESVR representative greeting you upon arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions. Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay. Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer. Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay. Access to our concierge services to help with booking nearby activities, tours and more.

Love at First Sight Welcome to “Heron’s Roost,” an exceptional 3-bedroom, 2.5-bathroom haven nestled on 10 picturesque, wooded acres with 400 feet of waterfront on Grace Creek. This charming residence is designed for your comfort, featuring a thoughtfully laid-out floor plan that encompasses a charming living room, beautifully decorated bedrooms upstairs and down, and a seamless flow between the kitchen and dining areas. Step outside to discover a wonderfully secluded backyard oasis, complete with an outdoor dining area, gazebo, duck blind, grill, oversized outdoor chess/checkerboard, and a private 75 ft dock. Whether you’re enjoying a morning coffee amidst the calming water views or hosting a sunset get-together, this spacious estate offers the perfect backdrop for relaxation and exploration, surrounded by well-established trees that provide ample privacy and shade. Located in a quaint Talbot County neighborhood with shaded streets ideal for biking and walking, you’ll have kayaks and canoes ready for launch right from the sandy beach! Or bring your own small boat and use the boat ramp adjacent to the dock. Revel in the nearby charm of St. Michael’s, where you can explore mom-and-pop shops, specialty boutiques, farmers markets, wineries, local cafes, bars, and restaurants. Don’t miss your chance for ’love at first sight’—book your serene getaway today and experience the tranquility of waterfront living! Talbot County STR License STN 24-9 PROPERTY FEATURES: Waterfront: Grace Creek Dock: Private dock and 2’ MLW. Guests are permitted to tie a boat to the dock. Water Toys: 2 kayaks and 2 canoes are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Crabbing Gear: Crabbing gear is available for guest use. Grill: Propane grill available for guest use. WiFi: High speed broadband internet is available through Breezeline internet. BED SIZES: Queen- 1 / Full - 1 / Full - 1 / Twin - 2

Talbot County STR License STN-22-32 This impressive 5BR, 4.5BA waterfront home was fully renovated in 2020 and provides the perfect place to host your family get-togethers. The magnificent, panoramic views of Harris Creek and Tilghman Island are framed eloquently by an expansive great room with 12’ x 8’ glass bifold doors that open fully onto a large outdoor deck facing the water - effectively inviting the outdoors in! The great room seamlessly connects to the nearby chef-inspired kitchen, overflowing with counter space and a large butcher block island perfect for communal cooking - get those kids busy cutting potatoes! Between the house and the waterfront, there’s ample space for unwinding on the hammock, playing a pickup game of soccer, searching for crabs or fossils on the 300-foot shoreline or lounging around the pool - all of which is visible from the kitchen and great room - perfect for keeping an eye on the kids while cooking or entertaining. Rainy days? Hole up in the library to read a book, play some board games...or curl up on the couch to stream a movie on the projector screen. Or head into St Michaels - it’s only an 11-minute drive from some of the cutest restaurants, local mom & pop shops, boutiques, cafes, bars, wineries and farmers markets. Such a charming example of Talbot County’s overall charm. Enjoy Chesapeake Bay living at its finest! This unique vacation home won’t last long. Book your getaway today.

Shorely, this is a true outdoor paradise! Originally a waterman’s cottage, Neavitt Cottage has been tastefully updated (super fast wifi!) while maintaining its original charm and character. Located along Balls Creek, which branches off the Choptank River, Neavitt Cottage’s location in the quaint village of Neavitt provides a peaceful and quiet country setting, yet is just minutes away from all that St. Michael’s has to offer. Enjoy crabbing, fishing, kayaking, boating, and sunset views off the new dock or have land based fun playing cornhole in the expansive backyard. The large screened in back porch is the perfect place to relax or enjoy your summer crab feast and has unobstructed views of the water. The sandy beach offers an easy kayak launch and kids will love to explore the shoreline. Bald eagles, herons, osprey, and all sorts of waterfowl make the creek their home and you can get up close and personal on a quiet kayak ride, 2 dual person kayaks are included for your use, so please bring your lifejackets! The house is also fully stocked with board games, puzzles, and books for those quiet summer days. This is the perfect spot to make lasting memories with your family and friends while enjoying the Eastern Shore lifestyle! Neavitt Cottage offers an open floor plan featuring 2 first floor bedrooms and open kitchen, dining, and living areas. Two additional bedrooms and a full bathroom are upstairs. Talbot County STR License ST-643-DER PROPERTY FEATURES: Waterfront: Balls Creek Dock: Private dock with 3.5’ MLW, fish cleaning table, multiple water and 120V electrical hookups. Guests may tie a boat to the dock. Water Toys: 2 dual kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Outdoor Toys: Cornhole is available for guest use. Grill: Propane grill. Propane is provided. Fireplace: Wood fireplace is available for guest use. Wood is NOT provided. Pet Policy: Pets are not permitted. WiFi: Reliably fast (good for 6-8 people or up to 10 devices) BED SIZES: King - 1 / Queen - 1 / Queen - 1 / Single Bed - Twin Sized - 2 /

Lovely and serene-the perfect spot to nurture your soul! This newly renovated 3BR, 3BA Sherwood waterfront vacation home is designed with your comfort in mind. Conveniently located halfway between St Michaels and Tilghman Island, and walking distance from Lowe’s Wharf. Some property features include: Private Dock Kayak Paddle Board Grill Outdoor Dining Area The free-flowing floor plan features a character-filled interior and comes complete with a separate dining room, perfect for family meals or game nights. Enjoy cooking again in this chef-inspired recently upgraded kitchen with breakfast bar. The oversized main suite is roomy and comfortable with 180 degree water views and a spacious bathroom. Enjoy the beautifully maintained property that comes complete with two screened porches and a private dock with amazing natural views. Take in the breathtaking morning sunrise from the water on the kayak or stand up paddle board. Tucked away on a quiet, dead end street in a historic fisherman’s village, at Sailor Joe’s you’ve found idyllic waterfront living. Be prepared for ’love at first sight’. Book your relaxing getaway today. Talbot County STR License STN-26-32 PROPERTY FEATURES: Waterfront: Harris Creek Waterhole Cove Dock: Private dock. Guests are not permitted to tie a boat to the dock. Water Toys: 1 kayak and 1 paddle board are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Family Friendly: 2 pack and plays and a baby booster seat is available for guest use. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

Enjoy “the good old days” in style! This exceptional 4-bedroom, 3.5-bathroom home offers a character-filled interior and comes equipped with a formal dining room, large entertainment spaces and an expansive great room. Enjoy the well-equipped kitchen that has been beautifully maintained and features a sprawling granite countertops island. The well-proportioned master suite is a secluded retreat that boasts an ensuite bathroom and waterfront views. The inviting interior features original hardwood flooring throughout. The tranquil backyard boasts a screened porch and private dock. A wonderful space for fishing, cycling, crabbing, entertaining or romantic cocktails for 2. Just the rural atmosphere you’ve been looking for! Perfectly situated in a desirable Talbot County neighborhood. A rare opportunity. Early booking is recommended! Talbot County STR License STN-22-4 PROPERTY FEATURES: Waterfront: Tred Avon River Dock: Private dock. Owner keeps a boat at the dock. Guests are permitted to tie a boat to the dock. Water Toys: 1 kayak is available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Grill: Propane grill. Propane is provided. Fireplace: Wood burning. Wood is not provided. Pet Friendly: This is a pet friendly rental. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: King - 1 / Queen - 1 / Single Bed - Twin Sized - 2 / Crib - 1 / Single Bed - Twin Sized - 2 /