Holiday rentals in Tisbury

The exterior of a two-story house is showcased, featuring weathered wooden shingles and a sloped roof. A balcony extends from the upper level, providing outdoor space. A small deck and entrance door are visible on the lower level, surrounded by trees and greenery.

4.95 out of 5 average rating, 85 reviews

Vineyard Haven Guest House - A/C, Walk to Town

Queen bed up (large carpeted master suite/living room with vaulted ceiling, ceiling fans, and walk out to deck, This End Up Couch Set), bedroom with 2 twins down, full bathroom (renovated 2023) on first floor, AC throughout the house, washer dryer, 42" flat screen TV with Amazon Firestick and internet based Xfinity cable, grill, outdoor shower and hardwood floors downstairs. Short walk to downtown Vineyard Haven and short drive to many popular beaches! Quiet dead end street with own driveway.

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5.0 out of 5 average rating, 28 reviews

Main Street steps from ferry

This freshly renovated 1 bedroom unit is a three minute walk from the Vineyard Haven ferry. Across the street begins Main Street Vineyard Haven with coffee, restaurants, shopping and local buses to everywhere. This one bedroom has a king bed in the bedroom and a comfortable brand new modern king pull out bed in the living room. There is also a twin rollaway bed. Full kitchen, sweet private small deck w seating for two overlooking Memorial Park. Perfect for visiting without a car. Free parking.

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4.92 out of 5 average rating, 192 reviews

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

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A cozy outdoor seating area is arranged with several white lounge chairs on a gravel surface. A brick fireplace is positioned near the house, accompanied by potted plants and a view of the deck area adorned with covered furniture in the background.

4.97 out of 5 average rating, 355 reviews

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

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5.0 out of 5 average rating, 44 reviews

Entire in-town cottage, walk to ferry/town/shops

LOCATION! Super cute, freshly renovated & professionally decorated 2+ bedroom Vineyard cottage w/ parking, just 2 blocks from downtown & all the action! Shops, restaurants, supermarket, harbor access & the main island ferry terminal are all literally just down the road. Although quaint, the cottage has 2 bedrooms w/ queen beds, full kitchen, a living room w/ a large TV & electric fireplace & there is another room upstairs w/ a workspace, small reading area & daybed for a guest.

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4.97 out of 5 average rating, 100 reviews

Guest house in Tisbury

Island Home. Secluded guest house in spacious yard

A secluded guest house with southern views over an expansive garden. Two blocks to downtown, the ferry, town pier and beach, restaurants, and public transportation to the rest of the island. This property is a refuge in Vineyard Haven’s historic district. Use our bikes to explore the island, or enjoy the short walk down Main Street to town beaches and fine dining. On site parking is available, or leave your car on the mainland and enjoy the easy walk from the ferry.

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4.97 out of 5 average rating, 114 reviews

A scenic view is captured showcasing a vibrant sunset over the water, with sailboats gently floating. The sky displays rich hues of orange and pink, reflecting on the calm surface, creating a serene atmosphere.

Guest house in Tisbury

MV King bed, Water Views, Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay. :)

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Superhost

A spacious living area is highlighted by a large blue sectional sofa, complemented by several accent pillows. Large glass doors provide a view of the deck, while pendant lights hang from a vaulted wooden ceiling, enriching the open atmosphere.

4.69 out of 5 average rating, 213 reviews

Carolyn's Vineyard Haven

LOCATION LOCATION LOCATION! Come enjoy this beautifully renovated 2000 + SF home, featuring 6 beds, 2 living rooms, 3 full marble baths, outdoor shower, and laundry. There are 2 decks with seating and grill area with plenty of trees for privacy. It is a 3 minute drive to VH ferry, 5 minute walk to Main Street shops/ restaurants and 5 minute walk to Tashmoo for a nice swim. Very close to Edgartown and Oak Bluffs making this a great location!

ValueFamilyQuiet

4.79 out of 5 average rating, 261 reviews

A raised ranch is surrounded by lush greenery, with large windows allowing natural light to fill the interior. A spacious deck extends from the front, providing outdoor seating options. The home is elevated, partially obscured by surrounding trees, and features a charming sloped roof.

Home in Oak Bluffs

Central location for your vacation

An apartment in a peaceful Raised Ranch! Your Martha’s Vineyard sanctuary. Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 8 minutes away from ferry. Great for family vacation, Island explorations, work trips, hosting wedding guests, wellness retreat, or just a simple gateway, this home will compliment your Martha’s Vineyard experience.

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4.89 out of 5 average rating, 177 reviews

The inviting living area features a white couch adorned with accent pillows, complemented by a striped ottoman. A cozy armchair is positioned nearby, and a piece of artwork hangs on the wall. Natural light filters through the window with wooden shutters.

Flat in Tisbury

Martha's Vineyard Pied-á-terre #2 Vineyard Haven

Martha's Vineyard Pied-á-terre # 2 Vineyard Haven is but a short stroll from the ferry. Found in the heart of Vineyard Haven, this beautiful apartment is in the center of our village and it's mix of restaurants, shops, galleries and theaters. A seamless blend of comfort and convenience! If your dates are not available you can check our neighboring property Martha's Vineyard Pied-á-terre #1 Tisbury

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The cottage is set in a lush green yard with well-maintained grass and bordered by trees. A stone pathway leads to the front porch, framed by shrubs and plants. The home features a charming exterior with shingle siding and multiple windows, inviting natural light inside.

4.97 out of 5 average rating, 60 reviews

The Pearl: Lovely cottage, close to VH town/ferry

THE PEARL is a lovely retreat for up to two couples. Come relax in this quaint cottage, close to town, beaches and ferry. Located in a quiet, residential neighborhood. Large yard and plenty of off-street parking. Walk to nearby beaches and restaurants. Significant DISCOUNTS for longer stays. Make an INQUIRY! Rent bikes or take island buses or taxis/Ubers. FRIDAY TO FRIDAY rentals in summer.

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The cottage is adorned with warm, glowing string lights that outline the roof and windows, creating a welcoming ambiance. A lush wreath decorates the front door, while charming wood paneling and multiple windows enhance the inviting exterior.

4.96 out of 5 average rating, 320 reviews

Not Your Great Aunt's Island Cottage

In the heart Vineyard, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Easily walkable to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

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Popular amenities for Tisbury holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Tisbury

A bright living area features a gray sectional sofa facing large windows, allowing natural light to fill the space. The vaulted wood ceiling adds warmth, while the kitchen is equipped with stainless steel appliances and a wooden dining table, enhancing the open-concept design.

5.0 out of 5 average rating, 40 reviews

Family Friendly 5 BR, Walk to Town, Beach & Ferry!

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A charming cottage is surrounded by flourishing gardens and green grass. The wraparound porch is adorned with latticework and floral accents. The building features a classic New England style with multiple windows and gabled roof, inviting natural light into the home.

5.0 out of 5 average rating, 98 reviews

Classic Vineyard Cottage - Steps to Beach/Downtown

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The exterior of the home displays a classic Cape Cod style with weathered shingles, accented by red doors. Sunlight illuminates the large front lawn, where manicured bushes and trees frame the welcoming entrance and wooden deck.

4.97 out of 5 average rating, 33 reviews

Charming In-Town Retreat | Private Outdoor Spaces

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A modern kitchen is presented with a spacious island featuring a laptop, decorative plants, and a tray. Sleek gray cabinetry and stainless-steel appliances are complemented by soft lighting from pendant lamps. Natural light filters through nearby windows, enhancing the inviting atmosphere.

4.97 out of 5 average rating, 71 reviews

Entire house walking distance from ferry!

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4.98 out of 5 average rating, 41 reviews

A charming two-story house with a light-colored exterior is set against a clear blue sky. The entrance features a welcoming porch and colorful blooming plants. A gravel driveway leads to the home, with steps guiding to a second-floor deck, and lush greenery framing the property.

Flat in Tisbury

Immaculate Coastal Retreat!

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The exterior of the home features a blend of modern architectural styles with traditional elements. A welcoming entrance door is framed by well-maintained gardens, and the private, landscaped yard is enclosed by a white fence. A Belgian block driveway provides ample parking space.

4.93 out of 5 average rating, 74 reviews

Classic Downtown Property

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A living area features a comfortable gray sofa adorned with patterned cushions, positioned beside a light-colored coffee table. A small vase with white flowers sits atop the table, accompanied by two glasses and a bottle. Soft light emanates from a lamp, illuminating the warm wood accents and inviting ambiance.