Dukes Area Rentals
From $782 per night (USD)VRBO
Charming home away from home near lagoon pond w/ boat launch
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Island Sanctuary The Space: This inviting and comfortable Oak Bluffs vacation home awaits your stay! With ...
From $782 per night (USD)VRBO
From $1772 per night (USD)Expedia
Bright spacious downtown home w/ guest house; walk to beach & lighthouse
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Heart of Edgartown The Space: Welcome to your idyllic retreat in the heart of Edgartown, MA, where relaxat ...
From $1772 per night (USD)Expedia
From $821 per night (USD)VRBO
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Brewster House The Space: Come and experience Oak Bluff's beautiful beaches, quaint shops, and cozy restau ...
From $821 per night (USD)VRBO
From $988 per night (USD)Expedia
Gorgeous 3-bedroom house with AC in West Tisbury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This charming home is the perfect base for your trip to the Vineyard. With three cozy bedrooms, including a king bed and ...
From $988 per night (USD)Expedia
From $913 per night (USD)VRBO
East Chop Oasis, Oak Bluffs, MA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of East Chop, this newly renovated 3 Bedroom, 2 Bathroom home is close to town, beaches, shops, res ...
From $913 per night (USD)VRBO
From $1089 per night (USD)Expedia
Stylish Renovated Home by Sengekontacket Pond
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Stylish and newly renovated, this coastal home sits just across The Boulevard from Sengekontacket Pond, offering distant ...
From $1089 per night (USD)Expedia
From $625 per night (USD)VRBO
Centrally located Island getaway with bike path access, patio, W/D, & games
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Cozy Island Cabin The Space: Escape to this charming cape cod style cabin in Edgartown, MA, where rich woo ...
From $625 per night (USD)VRBO
From $1115 per night (USD)Expedia
Modern Farmhouse in OB, walk to Beach and Restaurants
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly renovated house in Oak Bluffs with modern decor, walk to downtown OB and beaches. Convenient & Quiet! Newly reno ...
From $1115 per night (USD)Expedia
From $815 per night (USD)VRBO
Charming 2BR Guest House w/ Pool - Perfect Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this private, tranquil guest house on a secluded road with easy access to nature and a scenic walk to the stat ...
From $815 per night (USD)VRBO
From $1727 per night (USD)Expedia
Amazing sunsets, a welcoming home, and island adventures. Lifetime memories!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Gracefully situated atop the hills of Spring Point in Chilmark, our 4 BR (sleeps 8-10) home features panoramic water vi ...
From $1727 per night (USD)Expedia
From $734 per night (USD)VRBO
Chic Oak Bluffs Renovated 3-BR with Hot Tub, Large Yard, and Short Walk to Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Space Welcome to The Retreat at Towanticut, a chic coastal escape where upscale comfort meets effortless Vineyard ch ...
From $734 per night (USD)VRBO
From $2376 per night (USD)Expedia
Spacious, historic, air-conditioned 8-BR 4-BA beauty in the heart of Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 20
Oak Bluffs is waiting for you at this 8-bedroom house. With 2 king beds, 4 queen beds, 3 full beds, and more, this encha ...
From $2376 per night (USD)Expedia
From $753 per night (USD)VRBO
Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy seclusion surrounded by woods on this private This heavily landscaped house offers a furnished patio with a gas gr ...
From $753 per night (USD)VRBO
From $836 per night (USD)Expedia
Charming 3BR Cottage Near the Beach w/ Deck
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away in the charming town of Oak Bluffs, this delightful two-story house is the perfect retreat for a beach getaw ...
From $836 per night (USD)Expedia
From $1945 per night (USD)VRBO
Main House located on quiet cul-de-sac near town and walking trails to the water
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Set on a quiet cul-de-sac just one mile from downtown Vineyard Haven, this home offers easy access to neighborhood walki ...
From $1945 per night (USD)VRBO
From $2317 per night (USD)Expedia
Spacious 3-bedroom building in peaceful Tisbury with AC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom building is perfect for your escape to Tisbury. Each bedroom features a comfortable queen bed, offering g ...
From $2317 per night (USD)Expedia
From $561 per night (USD)VRBO
Edgartown Mermaid Loft on Martha’s Vineyard Sleeps Four--1.3 miles from town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Bright, brand-new one-bedroom apartment above a detached garage in Edgartown, offering a peaceful Martha’s Vineyard retr ...
From $561 per night (USD)VRBO
From $836 per night (USD)Expedia
Modern Downtown OB Condo, Stroll to Ferry & Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Space: Experience the ultimate Martha’s Vineyard getaway at 'Whale Tail,' a newly reimagined second-story sanctuary ...
From $836 per night (USD)Expedia
From $857 per night (USD)VRBO
Heart of Oak Bluffs, Walk to Beach & Ferries
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Space: Welcome to one of Oak Bluffs' most sought-after stays! Perfectly positioned above Vineyard Vines, this beaut ...
From $857 per night (USD)VRBO
From $893 per night (USD)Expedia
Irene's Hideaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Irene's Hideaway. Experience the perfect Vineyard retreat at Irene's Hideaway. This spacious 4-bedroom, 3-bat ...
From $893 per night (USD)Expedia
From $859 per night (USD)VRBO
Tranquil 4-bedroom house with AC near Lambert's Cove Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind in West Tisbury at this freshly renovated four-bedroom house, just a few minutes' walk to pristine Lambert's Cove ...
From $859 per night (USD)VRBO
From $1149 per night (USD)Expedia
Summer Beach Pass: Wooded Martha's Vineyard Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
1.4 Acres of Private Scenic Land | < 1 Mi to Waterfront Wildlife Area, 3 Mi to Long Point Beach Make Atlantic coastline ...
From $1149 per night (USD)Expedia
From $3954 per night (USD)VRBO
Serene 6-bedroom Vineyard Haven Retreat
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Your Dream Escape to Martha’s Vineyard Awaits Discover a luxurious retreat where elegance meets relaxation in the heart ...
From $3954 per night (USD)VRBO
From $927 per night (USD)Expedia
West Chop Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
*New to the market!* YOUR VINEYARD OASIS AWAITS! We can't wait to welcome you into our custom-built 3 bedroom, 2 bath h ...
From $927 per night (USD)Expedia
From $766 per night (USD)VRBO
Martha’s Vineyard Vacation Retreat - Relax!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to your perfect Martha's Vineyard escape! This beautifully renovated 3-bedroom, 2-bath house is nestled in a pea ...
From $766 per night (USD)VRBO
From $874 per night (USD)Expedia
Spacious, light filled 3-bedroom post & beam in West Tisbury steps to bike path
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in West Tisbury, this post and beam home is a dream. Guests will find three bedrooms featuring one king bed and ...
From $874 per night (USD)Expedia
From $813 per night (USD)VRBO
Artsy Vineyard Escape w/ Deck & Guest Suite
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Eclectic Oak Bluffs Retreat | Guest Suite & Sunny Deck Welcome to your Vineyard escape—an artful, light-filled home des ...
From $813 per night (USD)VRBO
From $989 per night (USD)Expedia
Charming 3-bedroom Cottage with AC in Oak Bluffs - Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our newly listed Oak Bluffs home! As we complete a few final touches, we’ll continue updating the listing wi ...
From $989 per night (USD)Expedia
From $2228 per night (USD)VRBO
Stunning Waterfront Cottage, Classic Vineyard Living in Edgartown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
**Updated Property** A rare find, this light-filled cottage is perfectly perched on the shoreline of Sengekontacket Po ...
From $2228 per night (USD)VRBO
From $893 per night (USD)Expedia
4-bedroom house in lovely Edgartown..Centrally located
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Located in Edgartown, enjoy what this 4-bedroom house has to offer. The space features a nice mix of beds, including a k ...
From $893 per night (USD)Expedia
From $958 per night (USD)VRBO
Walk to Beach! Oak Bluffs Home & Studio
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Directly on Scenic Bike Path | Walk to Coast & Downtown | 1 Mi to Ferry Catch the ferry and slip into a laid-back stat ...
From $958 per night (USD)VRBO
From $763 per night (USD)Expedia
Wooded Vineyard Retreat Near Beaches & Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Wooded Vineyard Hideaway Near Beaches & Trails Tucked away on a quiet, wooded lot in Edgartown, Massachusetts, this pea ...
From $763 per night (USD)Expedia
From $2607 per night (USD)VRBO
Steps to Beach: Martha's Vineyard Private Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
2 Mi to Ferry & 4 Mi to Airport | Pet Friendly w/ Fee | in-Home Laundry | Recently Renovated Experience the soul of the ...
From $2607 per night (USD)VRBO
From $1315 per night (USD)Expedia
4-bedroom house with pool and walking distance to Tisbury and Lake Tashmoo.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful house is the perfect home base for your trip to Tisbury. With four spacious bedrooms, including two king ...
From $1315 per night (USD)Expedia
From $1296 per night (USD)VRBO
THE HAVEN: No car needed 0.4 m to downtown/beach.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Nestled in Tisbury. Modern 5 bedroom 3.5 bath classic New England Colonial style home offers an exquisite blend of class ...
From $1296 per night (USD)VRBO
From $635 per night (USD)VRBO
Hidden Gem in the Heart of Edgartown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
You will be close to everything when you stay at this centrally located and spacious property. Right in the heart of Ed ...
From $635 per night (USD)VRBO
From $464 per night (USD)VRBO
Lovely 3-bedroom house with AC in Oak Bluffs within 15 min walk to Circuit/Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Some vacation rentals are just a place to sleep. Casa Luca is the kind of place you’ll talk about on the drive home, alr ...
From $464 per night (USD)VRBO
From $478 per night (USD)VRBO
Perfect One Bedroom Garage Apartment w/AC
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 4
This charming one bedroom is perfect for a couple or small family looking for a great space and in a great location just ...
From $478 per night (USD)VRBO
From $574 per night (USD)VRBO
Beautiful 4 BR/4 BA Modern Victorian: The Mack on Winemack
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful Victorian home has all the charm of a true Martha’s Vineyard Gingerbread cottage combined with all of the ...
From $574 per night (USD)VRBO
From $1508 per night (USD)VRBO
Aquinnah Home by Lobsterville Beach w/ Ocean Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
New VRBO tucked into Aquinnah’s quiet west end, this fully renovated Martha's Vineyard retreat has sun-drenched living s ...
From $1508 per night (USD)VRBO
From $1467 per night (USD)VRBO
Oak Bluffs Renovated Retreat With Pool, Tennis, and Sengekontacket Pond Access!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This 3-bed, 2.5-bath fully renovated townhome invites you to unwind with a community pool, tennis courts, and direct acc ...
From $1467 per night (USD)VRBO
From $3726 per night (USD)VRBO
Luxury 5 Bedroom Katama Estate With Pool / Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Located on one of the most sought-after streets in Katama, this renovated 5 bedroom / 3 full + 2 half bathroom home is s ...
From $3726 per night (USD)VRBO
From $542 per night (USD)VRBO
Lovely one bedroom cottage for a relaxing vineyard getaway.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your home away from home. One bedroom guest house in Edgartown recently built in Spring of 2025. This adorable guest ho ...
From $542 per night (USD)VRBO
From $15547 per night (USD)VRBO
Oceanfront Home w Private Beach!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
This spacious main house and guest house sit on the south shore of Chilmark, with an expansive yard and private stairs d ...
From $15547 per night (USD)VRBO
From $1657 per night (USD)VRBO
Sengekontacket Contemporary With Pool, Hot Tub And Water Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
POINT B EXCLUSIVE - Relax and unwind at this Sengekontacket Contemporary home featuring an indoor-outdoor design with mu ...
From $1657 per night (USD)VRBO
From $1355 per night (USD)VRBO
Edgartown Designer Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Katama, this fully renovated four bedroom three-and-a-half bath home offers ample space and a brand new pool ...
From $1355 per night (USD)VRBO
From $2718 per night (USD)VRBO
A magical home with pool and hot tub right off Katama bike path in Edgartown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This magical home right off the Katama bike path, a short bike to the beach and town, is as fun as it is relaxing! Ride ...
From $2718 per night (USD)VRBO
From $659 per night (USD)VRBO
Cottage Rental on Chappaquiddick Island with Transferable Ferry Ticket Availability Massachusetts
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Transferrable ferry tickets are available for the following dates for an additional charge: - June 28th til July 5th ...
From $659 per night (USD)VRBO
From $1480 per night (USD)VRBO
Newly Renovated 3 Bedroom Home in Edgartown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Enjoy easy island living in this beautifully renovated 3-bedroom, 1-bath home, just 2.3 miles from downtown Edgartown. T ...
From $1480 per night (USD)VRBO
From $1482 per night (USD)VRBO
Spacious 5BR Farmhouse Retreat on Martha’s Vineyard
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Bring the whole family to this beautifully refreshed 5-bedroom farmhouse in Edgartown’s quiet Dodger’s Hole neighborhood ...
From $1482 per night (USD)VRBO
From $775 per night (USD)VRBO
Winifred's Katama cottage. The perfect up island getaway, 2 beds 2 full baths.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This memorable cottage is the perfect home base for your trip to Edgartown. Guests will find two comfortable bedrooms, f ...
From $775 per night (USD)VRBO
From $3367 per night (USD)VRBO
2 BR, 1-bath condo, Facing Circuit Ave. 2nd floor. AC, WiFi. TV. No kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience the best of Oak Bluffs from this beautifully located 2-bedroom condo, just a short walk from the ferry—no ca ...
From $3367 per night (USD)VRBO
From $3732 per night (USD)VRBO
Cozy 4-bedroom condo in perfect Oak Bluffs with AC, on Circuit Ave, WiFi!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Escape to this delightful Oak Bluffs condo, perfectly located for enjoying all that town has to offer. With four comfort ...
From $3732 per night (USD)VRBO
From $1858 per night (USD)VRBO
Condo facing Kennebec with AC in charming Oak Bluffs, WiFi, TV, 2 Queen beds
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a peaceful stay at this condo in Oak Bluffs, there is one bedroom, with Queen bed, on the top floor with an outdoo ...
From $1858 per night (USD)VRBO
From $1033 per night (USD)VRBO
East Chop Escape - Water Views, Roof Deck & Minutes to Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm of Martha's Vineyard from this beautifully light-filled tri-level home in the highly desirable East ...
From $1033 per night (USD)VRBO
From $366 per night (USD)VRBO
Waterfront Retreat w/ Guest Cottage & Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Experience the beauty of Martha’s Vineyard from this private waterfront retreat overlooking the Lagoon in Oak Bluffs. Ne ...
From $366 per night (USD)VRBO
From $1207 per night (USD)VRBO
The Cottage - Part of a waterfront compound in Oak Bluffs, Martha's Vineyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Cottage, a well-appointed 2-bedroom home that is part of the waterfront compound that makes up 348 Sea Vi ...
From $1207 per night (USD)VRBO
From $1892 per night (USD)VRBO
Historic 6BR—Walk to Beach & Circuit Ave
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Stay in a spacious six-bedroom historic Colonial within walking distance of Circuit Avenue, Oak Bluffs Harbor and the be ...
From $1892 per night (USD)VRBO
From $510 per night (USD)VRBO
Cozy Cottage in Oak Bluffs - Close to town and beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Rustic, Walk-to-Town Cottage in the Heart of Oak Bluffs Set on a peaceful road just steps from the center of Oak Bluffs, ...
From $510 per night (USD)VRBO
From $693 per night (USD)VRBO
Edgartown Hydrangea: Walk to Everything
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
You will feel right at home in this owner/architect designed 3-bedroom, 2-bath house with original art in the heart of E ...
From $693 per night (USD)VRBO
From $631 per night (USD)VRBO
Charming Martha's Vineyard Cottage Minutes from the Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our family’s Oak Bluffs home on County Road is set up for easy summer living on Martha’s Vineyard. Sleeps up to 8 with a ...
From $631 per night (USD)VRBO
From $817 per night (USD)VRBO
Serene 3-bedroom condo in charming Martha's Vineyard Oak Bluffs.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has bee ...
From $817 per night (USD)VRBO
From $796 per night (USD)VRBO
Carole's Place- 2BR/2BA in Edgartown, Pool & Bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
**The Space** Carole's Place is a newly remodeled corner unit in Meetinghouse Village with tons of natural light and pr ...
From $796 per night (USD)VRBO
From $2378 per night (USD)VRBO
Modern West Tisbury Retreat 3BR/2BA Pool & Outdoor Shower
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience a relaxed Martha’s Vineyard summer in this beautifully built 3-bedroom, 2-bath home (2020) located in desirab ...
From $2378 per night (USD)VRBO
From $1003 per night (USD)VRBO
Edgartown 3BR House - Walk to Town, No Car Needed
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Garden House — a sun-filled three-bedroom home in the heart of Edgartown, Martha's Vineyard. Set right on ...
From $1003 per night (USD)VRBO
From $2929 per night (USD)VRBO
Lagoon Pond Waterfront with Private Dock
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Set on a quiet point on Lagoon Pond in Vineyard Haven, this private waterfront home offers something genuinely rare on M ...
From $2929 per night (USD)VRBO
From $1081 per night (USD)VRBO
Newly renovated home in Oak Bluffs. Walk to private beach on the Lagoon.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated home in Oak Bluffs, conveniently located between downtown Oak Bluffs and Vineyard Haven. Enjoy an ...
From $1081 per night (USD)VRBO
From $1582 per night (USD)VRBO
Oak Bluffs Harbor Gem
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Light open concept home with view of the Oak Bluff's Harbor across the street and an incredible nightly sunset. This co ...
From $1582 per night (USD)VRBO
From $2426 per night (USD)VRBO
Spacious 6-bedroom house in fantastic Oak Bluffs with AC
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to this beautiful house in Oak Bluffs. With six bedrooms, including five queen beds, a twin bed, and a bunk bed, ...
From $2426 per night (USD)VRBO
From $1038 per night (USD)VRBO
Aunt Clara's Cottage ~ Your Beautiful Island Home!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Your island time starts here. Set on New York Avenue in the heart of Oak Bluffs, Aunt Clara’s Cottage puts you steps fro ...
From $1038 per night (USD)VRBO
From $3155 per night (USD)VRBO
5-Bedroom Waterfront Retreat on Seaview Ave in Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Part of the exquisite waterfront retreat that is 348 Seaview Avenue in Oak Bluffs is the thoughtfully renovated 5-bedroo ...
From $3155 per night (USD)VRBO
From $1008 per night (USD)VRBO
Perfect 3-bedroom apartment with AC in peaceful Tisbury
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Located in Tisbury, this beautiful apartment offers a comfortable retreat for guests. With three bedrooms featuring a qu ...
From $1008 per night (USD)VRBO
From $787 per night (USD)VRBO
Lobster Talk: 4 BR home in Katama / Edgartown, quiet neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to LOBSTER TALK! Come relax in this quiet Katama neighborhood, close to South Beach and Edgartown village. Thi ...
From $787 per night (USD)VRBO
From $1010 per night (USD)VRBO
Perfect Vineyard escape steps away from Lagoon Pond and Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this beautifully updated 3-bedroom home, just 500 feet from Lagoon Pond—perfect for swimming, kayaking, and pa ...
From $1010 per night (USD)VRBO
From $798 per night (USD)VRBO
Beautiful 2-bedroom house with AC in Edgartown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This newly constructed guest house, completed in 2019, is located in the desirable Smith Hollow neighborhood of Edgartow ...
From $798 per night (USD)VRBO
From $1225 per night (USD)VRBO
5-bedroom, 3-bath house on 5 Acres in Chilmark
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Located just a 5 minute walk from Chilmark's famous North Tabor Farm, this charming house is a dream for families or gro ...
From $1225 per night (USD)VRBO
From $995 per night (USD)VRBO
Beautiful 5BR Oak Bluffs Home with AC - Walk to Beaches, Town & Ferry
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Enjoy the best of Oak Bluffs from this spacious 5-bedroom, 4.5-bath Martha’s Vineyard home. Located near downtown Oak Bl ...
From $995 per night (USD)VRBO
From $830 per night (USD)VRBO
Katama Getaway Walk to Norton Point/South Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Quiet neighborhood at the end of Katama.Wonderful biking on flat land trails,walk to Norton Point free boat landing or 4 ...
From $830 per night (USD)VRBO
From $880 per night (USD)VRBO
Hydrangea Cottage In Edgartown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
POINT B EXCLUSIVE - This renovated Classic Cape is tucked away in a peaceful in-town neighborhood, and offers a perfect ...
From $880 per night (USD)VRBO
From $777 per night (USD)VRBO
4-bedroom house in charming Vineyard Haven, easy walk to ferry, town and beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Lake Street house is a lovely, four bedroom, classic Vineyard home. You don’t need a car if you stay here, but there ...
From $777 per night (USD)VRBO
From $1261 per night (USD)VRBO
Recently renovated 4 Bedroom Home in Edgartown. 2 miles to South Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a peaceful stay at this 4-bedroom house in Edgartown. With 1 king bed with ensuite bath, 1 Queen bed, 1 bunk bed ...
From $1261 per night (USD)VRBO
From $510 per night (USD)VRBO
West Chop Tashmoo Beach Townhouse w/Pool Pickleball & Tennis borders Golf Course
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Ideal 3 bedroom, 3 full bath Townhouse in the coveted West Chop Tashmoo Beach neighborhood of Tisbury. First floor feat ...
From $510 per night (USD)VRBO
From $916 per night (USD)VRBO
Country Living at a Convenient Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Modern home on desirable Mockingbird Drive, Edgartown with two floor extension. Open bright contemporary feel with pine ...
From $916 per night (USD)VRBO
From $447 per night (USD)VRBO
The Pearl: Lovely cottage, close to Vineyard Haven town/ferry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
THE PEARL is a lovely retreat for up to two couples. Come relax in this quaint cottage, close to town, beaches and ferr ...
From $447 per night (USD)VRBO
From $1134 per night (USD)VRBO
Edgartown 5 bedroom home with two primary suites
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
New rental with prime weeks open! Centrally located in Edgartown yet privately set at the end of a street abutting a nat ...
From $1134 per night (USD)VRBO
From $1443 per night (USD)VRBO
Pet-Friendly Serene Martha’s Vineyard Cottage with Skylights in Edgartown, Massachusetts
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 10
This two-story, three-bedroom, two-bath, pet-friendly, serene cottage sleeps up to eight guests, and is situated on scen ...
From $1443 per night (USD)VRBO
From $570 per night (USD)VRBO
Third Floor 3BR Chimney Suite + Deck Access + Walk to Beach +Washer/Dryer
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Perched on the third floor, the Chimney Suite offers a private and spacious retreat just a short walk from the beach. Th ...
From $570 per night (USD)VRBO
From $3766 per night (USD)VRBO
Chilmark Estate with Pool & Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Discover a truly unique retreat just off the main road, yet worlds away. Nestled on a tranquil 22-acre estate in Chilmar ...
From $3766 per night (USD)VRBO
From $529 per night (USD)VRBO
Bright and airy 4-bedroom house on Chappy near Wasque
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Relax with your family and friends in this comfortable 4 bedroom upside down house, just a short walk to Katama Bay and ...
From $529 per night (USD)VRBO
From $1121 per night (USD)VRBO
3 Bed Edgartown Retreat: Central AC, Hot Tub, Private Yard & Easy Access to Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your private Edgartown retreat. Set in a quiet, peaceful neighborhood, this charming Martha’s Vineyard home ...
From $1121 per night (USD)VRBO
From $937 per night (USD)VRBO
Walk to Beach in Oak Bluffs - Private First Floor Retreat w/ Deck & Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect Martha's Vineyard getaway! This beautifully designed first-floor retreat offers comfort, space, ...
From $937 per night (USD)VRBO
From $532 per night (USD)VRBO
3rd Floor apt w/kitchenette + W/D & Private Entry + Walk to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Escape to the third floor of this spacious Oak Bluffs home, offering a private and comfortable retreat just a short walk ...
From $532 per night (USD)VRBO
From $948 per night (USD)VRBO
Gorgeous home in Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Have the perfect vineyard getaway at this beautiful home in Oak Bluffs. Only a 10 minute walk from the Oak Bluffs ferry ...
From $948 per night (USD)VRBO
From $3141 per night (USD)VRBO
5-bedroom house with Pool and hot tub in Edgartown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This luxurious home is ideal for your family getaway! It is conveniently located between Edgartown Village & South Beach ...
From $3141 per night (USD)VRBO
From $820 per night (USD)VRBO
Oak Bluffs Home Walk to Town, Beaches & Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
give me a less than 80 character headline for this description: Welcome to 22 Wing Road in Oak Bluffs, a newly renovate ...
From $820 per night (USD)VRBO
From $731 per night (USD)VRBO
Charming Pet-Friendly 4B Chappy Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Stay at our charming 4-bedroom Chappaquiddick Cottage and experience the best of Martha’s Vineyard while avoiding all th ...
From $731 per night (USD)VRBO
From $4645 per night (USD)VRBO
Spacious 6-bedroom house sleeps 12+ with pool, close to Tashmoo and pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Your home away from home in Vineyard Haven with 6 bedrooms. This marvelous house features 4 king beds and 2 twin beds, c ...
From $4645 per night (USD)VRBO
From $1506 per night (USD)VRBO
ISLAND GROVE: 4BR House in Quiet Edgartown Neighborhood w/ Ferry Tickets
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
ISLAND GROVE - This four bedroom home is located in a quiet Edgartown neighborhood with easy access to downtown and Kata ...
From $1506 per night (USD)VRBO
From $1577 per night (USD)VRBO
4-BR, Hot tub, Wifi, AC, Fire pit. No Pets.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Located in a very quiet Oak Bluffs neighborhood, two miles from the Atlantic Ocean and Town Center. Get ready for a vaca ...
From $1577 per night (USD)VRBO
From $596 per night (USD)VRBO
Brick Ranch On Cul-de-Sac with Central Air/Heat In Quiet Neighborhood Oak Bluffs
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This lovely house features 3 inviting bedrooms, Two each with queen beds and third bedroom with 2 twin beds and an upsta ...
From $596 per night (USD)VRBO