Home Vacation Home Rentals By Owner In Tisbury, MA

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Exceptional(69)

$3015.9

/ Nightly
Private Vacation Home

Downtown Captain's Mansion- The Dexter- Family, event, and pet friendly

Tisbury, Massachusetts, United States

The Dexter is the perfect place to stay on the Vineyard in ALL seasons. We have 9 bedrooms, 6.5 baths, an outdoor shower, private patio, 2 decks, grill, onsite parking, chef's kitchen, 6 living rooms, and w/d. Vehicle reservation included for guests who book July 5-11th 2026. AWESOME SPOT FOR YOUR CELEBRATIONS! 5min walk from the ferry boat and giant private parking lot. We welcome bachelorette parties, reunions, work retreats, etc, etc, etc. brbrAccepting books for summer 2027 Saturday-Saturday. brbrSleeps 18 people. brbrThe Dexter is a beautiful, historic whaling captain's house in downtown Vineyard Haven. The home was built in 1843 and has undergone creative design and renovations to modernize it into the stunning home it is now. We pair the old with the new and twist the traditional into modern. Each of our nine rooms features unique design and furnishings. Guests enjoy our numerous lounges and common areas, giant kitchen, wrap-around porch, patio, and yard. Several of our bedrooms have views of the harbor. We are located at 92 Main Street, in the heart of the action in Vineyard Haven. Walking distance from the restaurants, the harbor, the beach, and the best ice cream on Martha's Vineyard. We have 4-6 parking spaces in our lot (depending on what you drive). brbrBedroom locations: br1st floor: 1 queen bedroom. 1 bedroom with pullout sofa and 1/2 bath. 1 full bathroom with clawfoot tub/shower.br2nd floor: 2 king bedrooms with Jack and Jill bathroom. 1 queen bedroom with an en-suite.br3rd floor: Captain's suite up the back staircase has 1 king bed, sitting room, giant bathroom, and 1 double bedroom attached (double bedroom is also accessible from front staircase). 1 queen bedroom with en-suite. 1 double bedroom with en-suite.
Bed 9

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Bath 6

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Sleep 18

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Exceptional(4)

$1547.84

/ Nightly
Private Vacation Home

Stunning Tisbury Retreat with Pool

Tisbury, Massachusetts, United States

Escape to this brand-new luxury home in Vineyard Haven, minutes from downtown and the ferry.brDesigned for comfort and style, it features high-end interiors, a gourmet kitchen, and spacious living areas. With 5 bedrooms, 5.5 baths, central air, a home gym, a private heated salted water pool, outdoor shower and bar & grill area added for convenience. It's perfect for families or groups.brRelax in the king suites, unwind by the pool, or explore the island-your perfect Martha's Vineyard getaway awaits!brbrThe spacebrbrWelcome to this stunning, brand-new home on Bernards Circle — the perfect setting for your Martha's Vineyard escape. Ideally located just minutes from downtown Vineyard Haven restaurants, shops, harbor, ferry and 0.5 miles to the Tisbury Town Beach where you can swim, fish and enjoy occasional evening concert. This home combines upscale finishes with thoughtful design across three beautifully appointed levels.brbrThe Layout:brbrThree Levels of Comfort & PrivacybrLower Level (Private Apartment with Separate Entrance):brThis self-contained apartment offers flexibility and privacy - perfect for extended family, guests, or a work-from-home setup. It features:brbr* A queen bedroom with closetbr* A full bathroombr* A spacious living room with table gamesbr* Full kitchen and dining areabr* Laundrybr* Dedicated office/workspace or optional twin bedroombrbrGround Level (Main Living Space):brThe heart of the home is bright and inviting, with an open-concept layout ideal for gathering and entertaining.br* A fully equipped gourmet kitchen with large islandbr* Spacious living room with multiple seating areas, with TV and a beautiful fire place. Speakers throughout.br* Dining areabr* King suite with walk-in closet and ensuite bathroombr* Half bathroombr* Two entrances for easy accessbr* Garage gymbrbrUpper Level (Private Guest Wing + Primary Suite):brUpstairs offers both privacy and flexibility, with three bedrooms and three bathrooms:br* A queen suite with a ensuite bathroom, including a kitchenette and its own private entrancebr* A king primary suite with walk-in closet and a luxurious ensuite bathroom with a large soaking air jet tub, bidet, a walk in shower with rain head and double vanitybr* An additional queen guest bedroombr* A bathroom across the hallway for the guest bedroombr* Additional laundrybrbrOutdoor Living:brbrStep outside to unwind by the brand-new heated, saltwater pool and enjoy the serenity and privacy of the beautifully landscaped yard — perfect for sunny afternoons with barbecue and evening cocktails at the bar&grill area. An outdoor shower added for convenience. brWith 5 bedrooms and 5.5 bathrooms, this home comfortably accommodates families, friends, or multiple couples seeking a blend of space, style, and convenience. Whether you're planning a relaxing family retreat or a stylish summer escape, this Vineyard Haven gem is ready to welcome you in 2025.brSecurity cameras on external areas (front, sides and back of the house). brGuest accessbrGuests have access to the entire property.
Bed 5

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Bath 5

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Sleep 10

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Exceptional(2)

$1038.37

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Private Vacation Home

Vineyard Haven House: Beach, Fire Pit & Garden View

Tisbury, Massachusetts, United States

Summary:brbrEscape to Vineyard Haven House, a stunning holiday home perfect for your next getaway! This beautiful house boasts 4 spacious bedrooms, 2.5 bathrooms, and multiple living areas with cozy fireplaces. Enjoy direct access to the lake, a private dock, and fantastic outdoor amenities, including a fire pit, gas grill, and outdoor shower. Located in a tranquil neighborhood, you're just a short drive from beaches, shops, and the ferry to the islands. Relax and unwind in this idyllic retreat, offering the perfect blend of comfort and convenience.brbrbrbrThe Space:brbrBedrooms: 4 spacious bedrooms with comfortable beds and high-quality linensbrbrBathrooms: 2.5 modern bathrooms with luxurious finishesbrbrLiving areas: Multiple living areas with cozy seating, fireplaces, and stunning viewsbrbrKitchen: Fully equipped chef's kitchen with high-end appliances and ample counter spacebrbrAmenities: outdoor shower, fire pit, gas grill, paddle boards, kayaks, Smart TVs, and high-speed Wi-FibrbrOutdoor spaces: Expansive deck, patio, lawn, and dock with direct access to the lakebrbrbrbrGuest Access:brbrGuests have access to the entire house, including all bedrooms, bathrooms, living areas, kitchen, and outdoor spaces. Enjoy the use of the outdoor shower, fire pit, gas grill, paddle boards, Smart TVs, and high-speed Wi-Fi.brbrbrbrThe Neighborhood:brbrNestled in a peaceful residential area, our home offers a serene escape while still being conveniently close to local amenities. You're just a short drive away from a variety of shops and dining options. Discover the beauty of nearby beaches, explore scenic nature trails, and perhaps visit the local vineyards. For island adventures, a ferry is readily accessible.brbrbrbrGetting Around:brbrFor exploring the area, a car is recommended. The Martha's Vineyard Airport (MVY) is the closest airport, just a 15-minute drive away. The ferry terminal is also nearby, providing easy access to the islands.brbrbrbrOther Things to Note:brbrWe recommended an Uber driver to pick you up if necessary. It is many rental car options too.brbrbrbrInteraction with Guests:brbrI'm committed to making your stay at Vineyard Haven House as enjoyable as possible. I'll be available throughout your visit to assist with any questions or needs you may have. The best way to reach me is via the Airbnb messaging platform, where I typically respond within an hour. For urgent matters, you can also contact me through the platform, and I will do my best to address them promptly. I'm happy to offer recommendations for local activities, dining, or anything else you might need to enhance your experience. Your comfort and satisfaction are my top priorities!
Bed 4

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Bath 2

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Sleep 9

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Exceptional(11)

$390.64

/ Nightly
Private Vacation Home

Quiet 2BR Cottage for Creatives & Families — 7‑min Walk to Downtown

Tisbury, Massachusetts, United States

brSummer Street MV - where the spirit of summer livesbrLight-filled 2BR, 1BA cottage in the heart of Vineyard Haven - a 7–10 minute walk to the ferry, Main Street cafés, and beach. Ideal for journalists and creatives who need a calm workspace (fast Wi‑Fi, dedicated desk) or small families seeking a convenient island base.brbrLocated on a quiet, pretty residential street, vaulted ceilings greet you as you enter the living room, which is illuminated by skylights and stained glass windows rescued from a local whaling church. Enjoy the rustic charm and quietude of our space, thoughtfully designed for relaxation and rejuvenation. Whether you're reading, writing, or seeking solace, our cottage provides the ideal backdrop for your escape. Discover serenity at our A-frame retreat on Martha's Vineyard.brbrThere is a great tradition of culinary arts in this house. Built by one of the Island’s well-known chefs, our family has embraced this legacy over the last 25 years that we have lived on Martha’s Vineyard. We welcome you to expand upon this tradition during your visit. The kitchen features a 6-burner commercial stove, new refrigerator, and convection oven. We have stocked the kitchen with a French press and coffee maker, and a full selection of cooking vessels and tools so that you can cook your own breakfasts, local seafood, or whatever else catches your fancy. Consider hiring one of our recommended local chefs to cook for you one night in the house as a special treat.brbrThe eating nook seats 4 and receives morning light with cool cross breezes in the summer. Sections of the floors throughout the house are made from old slate roof tiles, including some laid out in the shape of a fish (or the Island depending on how you look at it) on the kitchen floor. brbrTwo bedrooms are available, including a spacious upstairs bedroom loft with a queen bed and desk to work (if you have to) and a bright bedroom downstairs with 2 twin beds. Downstairs we offer a large couch to relax in front of the television or listen to music, and the “best friends” seating area in front of the fireplace. We are excited to offer a newly built front porch, where you can sit and enjoy birdsong with your morning cup of tea, or late afternoon peace under the dappled branches of the honey locust tree. Likewise we now offer luxury Onsen waffle towels. brbrExit the back door to an intimate shaded patio with a table and benches, and an outdoor shower privately located around the corner in the wooded backyard. The yard is large enough to play frisbee or lounge around! Keep watch for the fireflies in the summer time. We are excited to offer you use of our “green egg” smoker/grill as well.
Bed 2

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Bath 1

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Sleep 4

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Exceptional(3)

$1339.28

/ Nightly
Private Vacation Home

Modern 4BR Escape • w/ Jeep Wrangler • Near Town • Patio, Fire Pit & Hot Tub

Tisbury, Massachusetts, United States

Welcome to your vacation retreat! This recently renovated single-family near downtown Vineyard Haven blends high-end finishes, modern amenities, and stunning outdoor spaces. With 4 bedrooms and 3.5 bathrooms, including two primary suites with walk-in showers, this property is designed for both comfort and convenience. brbrInside, you’ll find a spacious gourmet kitchen with a massive island and dual sinks, perfect for entertaining or preparing family meals. The kitchen is fully equipped for guests who love to cook at home. Great air conditioning throughout ensures a cool and comfortable stay throughout the house.brbrThe real magic awaits outdoors. Relax in the beautifully landscaped yard featuring ornamental trees, a tranquil fish pond with waterfall, and a blue stone patio ideal for lounging. Gather around the outdoor gas fire pit, fire up the grill, or unwind in the 4 person Hot Springs hot tub, surrounded within stone walls for total privacy. An additional private courtyard with outdoor shower completes the experience, offering a refreshing way to end a day at the beach.brbrThis home is thoughtfully stocked with everything you need for a seamless vacation: beach chairs, beach towels, linens, bath towels, shampoo, soap, and more. For added convenience, our 2026 4-door Jeep Wrangler RUBICON is optionally available for your stay. For insurance purposes, the Jeep has to be booked through Turo, but we’ve set the daily rate as low as Turo allows, making it a deeply discounted, guest-only benefit that feels like it’s basically included in the home. brbrWhether you’re here for family gatherings, a friends’ getaway, or a relaxing retreat, this property provides the perfect home base for creating unforgettable memories.
Bed 4

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Bath 3

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Sleep 8

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Exceptional(54)

$778.18

/ Nightly
Private Vacation Home

Newly built house, Central A/C, Walk to ferry, beach, and town

Tisbury, Massachusetts, United States

Completed in 2020. This modern 3 bedroom, 2 bath well appointed house is located within walking distance from downtown Vineyard Haven and the ferry terminal. The bike path and bus line are just steps away from the house.brbrAmenities include all new high end stainless steel appliances, central A/C, ERV fresh air ventilation system, eco friendly LED lighting, 2 SMART TVs, WiFi, outdoor patio, grill and spacious outdoor shower. The property has off-street parking for 3 cars.brbrThe first floor includes a fully equipped kitchen with a large island. The kitchen is open to the dining room and the living room. There is also a full bath, and a bedroom with a queen size bed. In addition, there is a separated mudroom with washer and dryer. brbrThe second floor has another full bath and two large bedrooms, each with its own thermostats. One bedroom includes a king bed, and a convertible couch that folds out to a twin bed. The other bedroom includes a queen bed. All bedding, linens, and towels are provided.brbrThe basement is finished, air-conditioned, and has a sitting area with a large SMART TV, and an extra refrigerator. brbrOff the dining room, step out to the sunny patio with a gas grill and outdoor furniture. There is also a new shed to keep any bikes, or items you may want to lock up outside. In addition, there is a big outdoor shower to use as you wish.brbrBeach chairs, umbrellas, a cooler, ice packs, and beach towels are included in the rental.brbrThis is literally a brand new property, completed in 2020. Everything is new!brbrbr
Bed 3

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Bath 2

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Sleep 6

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Exceptional(3)

Select Dates for Price
Private Vacation Home

Beautiful, sunny historic home, walk from VH ferry!

Tisbury, Massachusetts, United States

Beautiful, sunny and inviting home just a five minute walk from Vineyard Haven town center and ferry terminal. Only a short walk to town beach or take the bus to any of the islands surrounding villages including Edgartown and Oak Bluffs. brbr- The space includes an updated kitchen with Viking ovens and induction cooktop, as well as granite breakfast bar and stools. br- Separate dining space that can seat 8. br- Two comfortable living rooms- one on the first floor and one on the second floor outside of bedrooms, perfect for kids to play in. br- Large yard, perfect for whiffle ball, volleyball, and lawn games.br- First floor includes primary bedroom with updated primary bathroom with outstanding double headed shower. br- Second floor has two bedrooms with comfortable queen beds. One of these two bedrooms has bunk beds in it, alongside the queen. Also on the second floor, is a small bedroom with a single bed and crib. br- In basement is the 4th queen bed with full bath.brbrDisclosures about the property: br- There is no central air conditioning. However, there ARE air conditioning units in the bedrooms. With the bedrooms cooled, we find the house is completely fine with sea breeze throughout home during the day. br- Windows are on the older side. We keep multiple windows propped open and ask they they not be moved. br- Three full baths: one off of primary bedroom, second is upstairs for additional bedrooms, and third is in basement. There is also another bathroom off of the dining area for overflow use.
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Bath 3

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Sleep 8

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$422.71

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Private Vacation Home

West Chop Tashmoo Beach Townhouse w/Pool Pickleball & Tennis borders Golf Course

Tisbury, Massachusetts, United States

Ideal 3 bedroom, 3 full bath Townhouse in the coveted West Chop Tashmoo Beach neighborhood of Tisbury. First floor features a cathedral ceiling living room full of windows, natural light & fireplace. This desirable center unit provides a fully spacious open floor plan connecting to the dining room, eat in kitchen and counter bar. Den with french doors & adjacent full bath provide first floor bedroom/office option. Large re-finished deck overlooks beautiful woods. Second floor features a master suite with vaulted ceiling, spacious bath with jacuzzi & large walk-in closet. Second floor windowed balcony provides views of woods & lower living space leading to guest bedroom with ensuite full bath. Garage provides for one car with a workbench, utility & storage space & adjacent outdoor shower. Ideal location offers trails to walk, bike or drive to private or public beaches on Vineyard Sound & Lake Tashmoo. Association also provides a private dock, heated pool, tennis, pickleball and basketball courts and playground, all on 100+ acres of association land! Adjacent to Mink Meadows Golf Course & minutes from downtown Vineyard Haven. This truly unique combination of living space, location and amenities also offers hiking trails leading to beach and lakeside sunsets! PS We have rented through local realtors for many years. This is our first year on VRBO so we do not have any current reviews posted, but would be able to provide feedback from prior tenants upon request.
Bed 3

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Bath 3

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Sleep 5

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Exceptional(5)

$681.85

/ Nightly
Private Vacation Home

Sunny Vineyard Getaway Close to Everything steps from sound clean and comfy

Tisbury, Massachusetts, United States

Our spacious, airy home is a recently renovated one floor open concept home filled with natural light located on a private road. brbrThis 3BD/2BA ranch style home sleeps up to 6 brpeople making it the perfect destination for your family getaway. brbrYour next “home away from home” is perfectly located minutes from all the amenities and conveniences of Vineyard Haven.brbrPrepare gourmet meals and sandwiches for the beach using our fully appointed renovated kitchen (all stainless steel appliances updated 2023) brbrSpend time outdoors in our private fenced in backyard and dine outside El Fresco style on our large back deck with table seating under an umbrella. brbrOur Property Manager is on island and always available. Owners are always available by phone. brbrAdditional amenities:brBrand new beds and couches brBrand new Washer/Dryer brSplit unit Air and Bedroom ACs brPrivate master with ensuite bathroom and sliding door stepping out to cozy private deckbrBrand new Weber grillbrOutdoor shower brLinens and towels available for 150$ rental fee brbrJust 10 minutes from our home: brbrVineyard Haven - Minutes to ferry and town - explore local shopping and restaurants brbrWest Chop Loop Overlook - Finish your day with a popular after dinner sunset walk to the overlook for spectacular sunsetsbrbrLocal beaches to try: brStroll down to a local small beach two blocks away on vineyard sound and watch the ferries come in or go for a quick dip. Perfect spot for a kayak or canoe launch. brbrTashmoo Beach - 1.6 miles brOwen Park Beach - .9 mile away brVineyard haven town center 1.0 mile away brFerry dock 1.6 miles brbrLocal outdoor activities: brMink Meadows Golf Course - 5 minutes away brWest Chop Club - 5 minutes away brSheriff Meadows Hiking Trails - steps away brSome dates are available with ferry tickets.brbrWatch the runners go by “running the chop” on the fourth or July or try it yourself perfect loop from the home.
Bed 3

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Bath 2

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Sleep 6

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$1047.16

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Private Vacation Home

West Chop Hideaway

Tisbury, Massachusetts, United States

*New to the market!* YOUR VINEYARD OASIS AWAITS!brbrWe can't wait to welcome you into our custom-built 3 bedroom, 2 bath home, ~1,000 sq feet. Perfect for 1-2 couples or 3-4 friends. Conveniently located just about a mile from Downtown Vineyard Haven, and just steps from West Chop, it is easily walkable. We are located on a main road but the house is in a very quiet area. brbrEnjoy your morning coffee out on the covered front porch, or tuck away in the fenced-in back yard, where you can relax on the couch, enjoy a meal outside, or sit in the shade underneath an umbrella. brbrInside the home, you will find two full bathrooms, one bedroom with a twin bed, and two bedrooms with comfortable queen beds. Each bathroom is stocked with shampoo, conditioner, body wash, new hair dryers, some extra necessities like q-tips, razors, and toilet paper, etc. brbrChef's kitchen, complete with all stainless steel appliances, and the kitchen is stocked with whatever you might need for a meal at home. Such as a Vitamix blender, juicer, coffee machine, toaster, popcorn machine, new pots and pans, ice maker and wine fridge. Please note: we do not have a microwave. There is a washer/dryer, as well as new linens and towels.brbrCozy up on the couch for a night in and utilize the 55 smart tv equipped with all the apps (no cable, sorry).brbrNOTE: We love dogs, but our property is not currently dog-friendly. We please request that if you rent from us, you respectfully will not host any parties or events, that includes bachelor/bachelorette parties. This house is comfortable but quite small, and does not accomodate a lot of people. brbr2nd NOTE: There is mandatory housekeeping once a week. It is $200. This is required for each seventh day you are renting.
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Sleep 5

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Exceptional(30)

$1125.19

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Private Vacation Home

A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!

Tisbury, Massachusetts, United States

 The reviews say it all. We are a 5-star property because we surprise and delight our renters with not only a great home but also the details that matter: hot tub, gas grill, and intuitive use of the house (Every switch, drawer and shelf is labeled!), coffee start service, seasonal flowers, and sparking clean home cared for by our long-time cleaning staff. The most common comment we get is that the house is actually better than the photos allow! brbrWe are also 35-year veterans of the vacation rental market. Our family built its first home in Edgartown, MA in 1987, and my mother taught me the business. My husband has a degree in hospitality from the Honors College at the University of Houston (Go Coogs!), so you can imagine how we take care of the necessary details. Even if you do not choose our home, we recommend you ask your hosts how long they have been in the rental business. It makes a difference when you have a veteranbrbrOur custom-build home provides beautiful water views of Lagoon Pond, and yet the tough winds of the open sea are more rare, since the house is protected by the lagoon and the bluff it sets on. Surrounded by a protected forest called Land Bank and Sheriff's Meadow, this property is extremely private and offers easy access to miles of hiking trails and pristine waters. Enter the home from the covered porch; the main level features an open floor plan, high ceilings in the living areas - open to the dining room and kitchen, where large windows frame the Lagoon. Sleeps up to 8. Outdoor shower! br20% off 28+ daysbrbrSo many New England homes can be TIGHT - Tight driveways, tight rooms... Not The Bellevue! This home can accommodate 6 cars in the double driveway and has a flow about it where you probably will not bump into anyone in your party. And the patio is fit for a large family/group to enjoy.brbrWe also tend to the house every quarter, so we are constantly updating towels, dishes, glass ware, and sundries that we provide such as laundry detergent. When we are not there, our cleaners serve as our eyes and ears, so we replenish quickly. brbrHave you ever stayed at a house with radiant floors It's one of the reasons we have so many cold-month renters. It's a very well insulated and dry house with heated floors in many of the rooms. Lovely on your feet as you walk around.brbrLike to go for walks and hikes Head out the back door, down the trail and walk through the paths of the Sherriff's Meadow. You will spot wild turkeys and birds galore.brbrAnd the view is fit for the Obamas. In fact, they have seen this view, having attended conservancy and arts fund raisers at the house next door. br
Bed 4

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Bath 3

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Sleep 8

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