Vacation Rentals By Owner In Tisbury, MA

Showing 20 Of 78 Vacation Rentals

$204

One Bedroom Private Cottage on Large Quiet Property.

Tisbury, Massachusetts, United States

Up island feel with down island convenience. The private cottage sits on a large serene property nestled between tall trees with a wrap around deck. Walk to Vineyard Haven shops, restaurants and Owen Park beach. It's one mile to town and the ferry (2 min drive/15 min walk with sidewalks). Home features a sitting room with vaulted ceilings, kitchenette, 1 bedroom with queen bed, AC, and large bath with tub/shower.

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Exceptional(41)

$1,080

/ Nightly

Private Vacation Home

Elegant, spacious Home - Sleeps 12- Walk to town

Tisbury, Massachusetts, United States

This modern home boasts +5,000 square feet of living space w/ three beautifully decorated floors, including state of the art technology, resting on a large wooded lot within walking distance of downtown Vineyard Haven.brbrMain Level - includes great room, combo kitchen/dining room and open sun porch. Great room has large flat screen TV, home theater system and wireless internet. Central air conditioning plus ceiling fans. Dining seats 10+. Kitchen has all needed utensils, pots, pans, dishware. Large screened porch off kitchen. Generous deck overlooks backyard with outdoor seating area and grills. Also this level - MBR Suite with King bed and private bath.brbrSecond Level - includes second large MBR Suite w/ private bath, soaking tub and queen bed; 3 additional upstairs bedrooms: 2 BRs with 2 twin beds in each room; and 1 bdrm with 1 full, 1 twin; hall bath & laundry closet w/ washer & dryer. Second zone central air. SHEETS AND TOWELS ARE NOT PROVIDED BUT CAN BE RENTED.brbrWalk-out Lower Level - includes large recreation room w/ cable-tv., XBOX-video game system and ping pong table. Also, full bed in sleeping nook with adjoining full bath. Enjoy your vacation at this modern MVY home.

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Exceptional(56)

$1,255

/ Nightly

Private Vacation Home

Downtown Captain's Mansion- The Dexter- Family, pet, and event 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. AWESOME SPOT FOR YOUR CELEBRATIONS! 5MIN WALK FROM THE FERRY BOAT and private parking lot. brbrWe book Saturday-Saturday in peak season 6/28/25-8/28/25.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.

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Sleeps

Exceptional(20)

$975

/ Nightly

Private Vacation Home

Vineyard Haven Gem - A luxury rental on Martha's Vineyard

Tisbury, Massachusetts, United States

This home is the perfect back drop for your vacation memories. brbrThis newly constructed home has a comfortable, modern aesthetic with three large, well-appointed bedrooms each with a full private bath. The two bedrooms on the top floor are fitted with king beds and the bedroom on the lower level has twins. In addition, there are two high quality roll away beds.brbrThe fully-equipped kitchen and bar area come complete with stainless appliances and stocked with modern dishware and serving pieces that invite great family meals on the large farm table, which seats 8. An open floor plan allows seamless transitions between the living, dining and kitchen areas.brbrA wrap-around porch looks out onto a lush, private garden with bluestone patio and native stone retaining wall. Teak patio furniture, a shaded dining area, and a gas grill allow the festivities to continue outdoors.brbrCentral air-conditioning, an outdoor shower, bicycles, beach accessories and parking for three cars make this home away from home yours!brbrWalk to town, ferry and Owen Park beach! This new home located on a private road three blocks from downtown Vineyard Haven.brbrAS A REMINDER - Bed Linens and Towels are NOT provided. There are, though, plenty of blankets, pillows and beach towels in the home for your use.

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Sleeps

Exceptional(3)

Select Dates for Price

Private Vacation Home

Great update 3 BR near ferry with pool

Tisbury, Massachusetts, United States

Recently updated 3 bedroom 2 bathroom near Vineyard Haven Ferry and downtown restaurants. Walk to local spots easily. The house has been recently updated in 2020. The house has a rare private pool with spacious paved area for entertaining. The pool house is great for storage and in includes bikes and beach chairs. We just furnished and includes window unit AC. We own another house in the Vineyard and happy to help with recommendations.

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$750

/ Nightly

Private Vacation Home

Mitchell Manor MV

Tisbury, Massachusetts, United States

Fully Renovated Three bedroom, two full bath home within walking distance to shops and minutes from the ferry. Home located on a quiet Vineyard Haven Block. Perfect location one block from Main Street of Vineyard Haven and close to West Chop and Mink Meadows Golf Course.

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Exceptional(4)

$372

/ Nightly

Private Vacation Home

The Vienyard Haven Hideaway Apt

Tisbury, Massachusetts, United States

NEWLY RENOVATED! The Vineyard Haven Hideaway Originally built in 1925, this home has undergone a full gut renovation with finishes that meet all of today's modern standards.brbrLocated in Vineyard Haven within walking distance of town and beaches! Quick access to the Steamship Authority Ferry and bus route.brbrYour Martha's Vineyard vacation awaits you!brbrbrThe spacebrFirst-floor unit. DuplexbrThe spacebrFirst floor!brGuest accessbrEntire downstairs floor of our home. Separate entrances, no interior staircase between upstairs and downstairs.brOther things to notebrLet us know if you want access to a compost bin so you can recycle your food scraps during your stay!

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Exceptional(44)

$311

/ Nightly

Private Vacation Home

Newly renovated charming modern island home for your relaxing getaway

Tisbury, Massachusetts, United States

This open concept, recently renovated summer home is on a one acre woodsy property. The bedroom has a queen size bed and there is a queen size inflatable mattress that can be used in the living room. It has a full kitchen, with gas stove, full size refrigerator, dishwasher and stocked with all of your cooking needs (dining ware, pans, coffee maker, and utensils). Large cathedral ceilings with skylights will make for your perfect dining experience. At the end of your long beach day you can choose to enjoy the large outdoor shower or have a bath in the indoor bathroom. There is a large covered porch off of the dining room, which is great for evening entertaining and relaxing.brbrAmenities Include: beach towels, beach chairs, cooler, propane grill, flat screen smart-TV with cable, WIFI internet, boogie boards and beach toys, and a large private driveway for parking. brbrIf you are looking for a quiet summer home that is walking distance to town, ferry and the local beach, this is the rental for you!

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$1,783

/ Nightly

Private Vacation Home

Vineyard Haven Hideaway w/ fire pit, dining outdoor

Tisbury, Massachusetts, United States

Summary:brEscape to this stunning waterfront haven nestled on the shores of a serene lake.br This luxurious retreat offers breathtaking views, modern amenities, and ample space for families or groups of friends. Relax in the beach, soak up the sun on the deck, or explore the Beach!brbrThe Space:brBedrooms: 4 spacious bedrooms with comfortable beds and high-quality linensbrBathrooms: 2.5 modern bathrooms with luxurious finishesbrLiving areas: Multiple living areas with cozy seating, fireplaces, and stunning viewsbrKitchen: Fully equipped chef's kitchen with high-end appliances and ample counter spacebrAmenities: outdoor shower, fire pit, gas grill, paddle boards, kayaks, Smart TVs, and high-speed Wi-FibrOutdoor spaces: Expansive deck, patio, lawn, and dock with direct access to the lakebrbrGuest Access:brGuests 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.brbrThe Neighborhood:brThis tranquil retreat is located in a quiet, residential neighborhood, just a short drive from shops, restaurants, and attractions. Explore the nearby beaches, nature trails, and vineyards, or take a ferry from the islands.brbrGetting Around:brA car is recommended for exploring the area. The nearest airport is Martha's Vineyard Airport (MVY), which is approximately a 15-minute drive away. The ferry terminal is also conveniently located nearby, offering access to the islands.brbrOther Things to Note:brWe recommended an Uber driver to pick you up if necessary. It is many rental car options too.

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Exceptional(10)

$466

/ Nightly

Private Vacation Home

VH Bright and Airy Cottage - walking distance to downtown and beach

Tisbury, Massachusetts, United States

brSummer Street MV - where the spirit of summer livesbrWelcome to our tranquil A-frame cottage nestled in the serene beauty of Vineyard Haven, where you can enjoy destinations like The Black Dog, The Net Result, and Bunch of Grapes bookstore. Located on a quiet, pretty residential street a brief walk from downtown, 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. Perfect for artists and those seeking a peaceful retreat, our hideaway offers a serene atmosphere. Unwind amidst nature's embrace, where inspiration flows freely and creativity flourishes. Enjoy the rustic charm and quietude of our space, thoughtfully designed for relaxation and rejuvenation. Whether you're reading, writing, or simply 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.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.

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$794

/ Nightly

Private Vacation Home

Brand New Home in Vineyard Haven - Perfect Family Home Centrally Located on MV!

Tisbury, Massachusetts, United States

This BRAND NEW, recently built 4-bedroom, 3-bathroom home offers the perfect blend of comfort and convenience, situated within walking distance of downtown Vineyard Haven and the Steamship Authority. Step outside into the spacious yard, where you'll find a grill, outdoor dining area and outdoor shower, ideal for refreshing after a day of exploring the island's treasures. The property is also equipped with an E/V charger.

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Exceptional(42)

$697

/ Nightly

Cottage

WATERFRONT Downtown Cottage w/ Beach

Tisbury, Massachusetts, United States

This is one of the most unique properties on Martha's Vineyard. Located directly on the bustling Vineyard Haven harbor & right across the street from the famous Black Dog Tavern, this cottage offers a truly immersive waterfront Vineyard experience - right in the thick of everything. Everything you could need - from public transportation, to groceries, to restaurants, beaches and so much more - is literally just steps outside the front door. The house was just remodeled and outfitted with all new furniture and appliances. The house is comprised of a fully equipped kitchen, living room, small dining area, 2 outdoor decks, 2nd floor master bedroom with full bath, and a downstairs 1/2 bath. Off-street parking for up to 2 vehicles - which is like GOLD in that area! If you’re arriving by way of your own boat, dock space can be reserved in advance at The Black Dog Wharf, Vineyard Haven Marina and Tisbury Wharf Company.

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$807

/ Nightly

Private Vacation Home

Charming 2-bedroom house in iconic West Chop area with AC, WiFi

Tisbury, Massachusetts, United States

Down a quiet private lane you will find this newly renovated cottage with everything one could want for a vacation on Martha's Vineyard. Conveniently located within walking distance to downtown Vineyard Haven with all the fabulous restaurants and shops, VH Yacht Club, beaches and the library. This 2 bedroom (both bedrooms have gorgeous ensuite baths) home has a fully equipped kitchen with a breakfast bar, central air, separate dining space, internet, space in Primary suite with desk and chair and a bluestone patio to relax in the sun or shade. Primary suite has king bed and guest suite has queen bed. Linens/towels are provided. This newly renovated home is available June through begining of October. Prefer a monthly rental but flexible. The luxury and peacefulness will not disappoint. No pets allowed and no smoking.

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Exceptional(5)

$1,787

/ Nightly

Private Vacation Home

Entire Renovated Home w/ JEEP Wrangler, Near Town, Private

Tisbury, Massachusetts, United States

Spacious, modern, and privately situated home only 1.5 miles from downtown Vineyard Haven. Guests will have access to our 2018 4-door Jeep Wrangler (must sign a waiver). The house comes equipped with everything you will need to make this a your basecamp while visiting Martha’s Vineyard, including bed linens, beach chairs, towels, coolers, beach umbrellas, island maps, and more. The house is situated on 1.5 acres, so you'll enjoy nice privacy when relaxing at the house.

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Exceptional(2)

$1,015

/ Nightly

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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Exceptional(2)

$4,163

/ Nightly

Private Vacation Home

West Chop Sandy Beach, Water Front, 6 BR, Great Views!

Tisbury, Massachusetts, United States

Summers on the Vineyard don’t get better than this waterfront 6 bedroom, 5 bath home with its own private (and sandy) beach just 50 yards away! Excellent West Chop location. It’s a short walk to West Chop Club or easy bike ride to the Vineyard Haven Yacht Club. This home offers a unique set up with 4 big bedrooms surrounding a large great room over looking the Vineyard Sound. Just perfect for entertaining. On the other side of the butler pantry and kitchen area is another wing with 2 additional bedrooms over the garage with their own family room, full bath and elevated deck. There is parking for 6 including a 3 car garage. You will be blown away by the gorgeous sunrises as well as enchanting light as the sun sets reflecting off of East Chop and passing boats. This special home is fully stocked and ready for you to enjoy! PREFER FRIDAY TURNOVERS AND 7 NIGHT MINIMUM

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Select Dates for Price

Private Vacation Home

Tisbury - Airy 4-bedroom with Peaceful Pool

Tisbury, Massachusetts, United States

You'll have a great time at this quiet, clean, and comfortable place to stay. Walk to everywhere! Just minutes from the Vineyard Haven ferry landing, Owens Park beach, restaurants, and so much more. Or just relax in the pool.brbrOur house is 1600 sq. Feet, 2 story with private pool & an outdoor shower. We have a 5 night stay requirement. We offer a dining table inside for 8 and a outdoor table also for 8. There is a gas grill on the patio deck. The downstairs has 2 twin beds off the dining area and a queen bed off the living room area. Upstairs has a king bed and a desk if needed. There is also a room with 2 twin beds upstairs. Each floor has one bathroom with a shower (no tub). There is an outdoor shower. The downstairs bathroom has a washing machine & dryer.brbrOther things to note, there are 4 bedrooms, a dining area, living room and kitchen area. There are 2 bathrooms with shower stalls but no tub. There is an outdoor shower. We have a washer & dryer and supply laundry detergent.brbrWe have 6-8 beach chairs, 2 beach blankets, a beach towel for each guest and a couple of beach bags to carry your stuff. All for your use during the stay. You’ll be able to wash these items to reuse as with any linens you want to wash.

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$1,049

/ Nightly

Private Vacation Home

5 Bedroom Historic Main Street Vineyard Haven Home

Tisbury, Massachusetts, United States

In the heart of Vineyard Haven, this comfortable 5 bedroom home sets the scene for a fabulous Martha's Vineyard getaway. Walk to the ferry, great shops and restaurants, enjoy your coffee overlooking the sailboats in the marina, or set off for your walk or bike ride of the West Chop loop. This antique is well cared for to preserve its character while outfitted with modern comforts and high quality furnishings and bedding. The private patio is perfect for a cookout.

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$2,234

/ Nightly

Private Vacation Home

Harbor Front in Vineyard Haven! Brand New Construction - seconds from Town!

Tisbury, Massachusetts, United States

Discover a newly constructed 3-bed, 2.5-bath rental with captivating views of Vineyard Haven Harbor. Adjacent to the Steamship Authority, access is effortless. Enjoy an open-concept layout, gourmet kitchen, and a spacious deck. The primary suite has a private deck. Immerse in the Vineyard lifestyle with shops and restaurants nearby. Book now for an idyllic island escape.

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Sleeps

Exceptional(4)

$606

/ Nightly

Private Vacation Home

Family couples wedding guests romantic oasis convienent location big sunny deck

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 en-suite 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.

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Rent a place that suits your needs

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View 59 Private vacation home

Most popular vacation rentals in Tisbury

Exceptional(4)

$615.77

/ Nightly

Private vacation home

Family couples wedding guests romantic oasis convienent location big sunny deck

Tisbury, Massachusetts, United States

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Bath

Sleeps

Exceptional(4)

$1787.20

/ Nightly

Private vacation home

Entire Renovated Home w\/ JEEP Wrangler, Near Town, Private

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$355.25

/ Nightly

Apartment

Cozy studio with AC,WiFi, full kitchen, private entry great for couples vacation

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$486.73

/ Nightly

Private vacation home

Newly Renovated 3BR\/2BA - Walk to Restaurants

Tisbury, Massachusetts, United States

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Bath

Sleeps

Exceptional(4)

$504.75

/ Nightly

Private vacation home

Spacious home near the ferry & downtown with enclosed yard, games, & W\/D

Tisbury, Massachusetts, United States

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Bath

Sleeps

Exceptional(4)

$1172.85

/ Nightly

Private vacation home

Looking for a relaxing getaway? Convenience & Privacy in Vineyard Haven

Tisbury, Massachusetts, United States

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Bath

Sleeps

Exceptional(4)

$483.15

/ Nightly

Cottage

Cozy New TimberFrame Vineyard Haven!

Tisbury, Massachusetts, United States

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Bath

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Exceptional(4)

$2010.60

/ Nightly

Private vacation home

PRIVACY & RELAXATION ON MARTHA'S VINEYARD

Tisbury, Massachusetts, United States

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Bath

Sleeps

Exceptional(4)

$4141.31

/ Nightly

Private vacation home

West Chop Sandy Beach, Water Front, 6 BR, Great Views!

Tisbury, Massachusetts, United States

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Bath

Sleeps

Exceptional(4)

$420.04

/ Nightly

Cottage

Entire cottage, walk to\/from ferry & downtown, newly renovated, parking on site

Tisbury, Massachusetts, United States

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Vacation Rentals By Owner In Tisbury, MA

$204

$1,080

$1,255

$975

$750

$372

$311

$1,783

$466

$794

$697

$807

$1,787

$1,015

$4,163

$1,049

$2,234

$606

Rent a place that suits your needs

Most popular vacation rentals in Tisbury

$615.77

$1787.20

$355.25

$486.73

$504.75

$1172.85

$483.15

$2010.60

$4141.31

$420.04

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