Oak Bluffs Rentals
From $676 per night (USD)VRBO
Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Your stay in this charming second-floor corner two-bedroom, two-bath unit is made comfortable with all the ess ...
From $676 per night (USD)VRBO
From $400 per night (USD)Expedia
Island Inn - Residential Suite - 30G - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: Your stay in this charming first-floor corner one-bedroom, half-wall bedroom, one and half-bath unit is made c ...
From $400 per night (USD)Expedia
From $352 per night (USD)VRBO
Island Inn - Residential Suite - 37G - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $352 per night (USD)VRBO
From $685 per night (USD)Expedia
Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Your stay in this charming second-floor corner two-bedroom, two-bath unit is made comfortable with all the ess ...
From $685 per night (USD)Expedia
From $355 per night (USD)VRBO
Island Inn - Queen Studio - 24F - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $355 per night (USD)VRBO
From $338 per night (USD)Expedia
Island Inn - King Studio - 27F - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $338 per night (USD)Expedia
From $407 per night (USD)VRBO
Island Inn - Studio Suite - 18D - Dog-friendly - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Your stay in this charming first-floor corner two-bedroom, one-bath unit is made comfortable with all the esse ...
From $407 per night (USD)VRBO
From $347 per night (USD)Expedia
Island Inn - Studio Suite - 3B - Dog-friendly - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This cozy and convenient ground-floor rental offers everything you need for a restful and comfortable stay. Th ...
From $347 per night (USD)Expedia
From $371 per night (USD)VRBO
Island Inn - Studio Suite - 13D - Dog-friendly - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Step into this inviting suite that offers a perfect blend of comfort and functionality. This unit features two ...
From $371 per night (USD)VRBO
From $414 per night (USD)Expedia
Island Inn - Residential Suite - 38G - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $414 per night (USD)Expedia
From $559 per night (USD)VRBO
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Your stay in this charming second-floor corner two-bedroom, one and half-bath unit is made comfortable with al ...
From $559 per night (USD)VRBO
From $949 per night (USD)Expedia
Island Inn - Cottage - 21E - Oak Bluffs, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Your stay in this charming first-floor corner two-bedroom, each with a Queen Bed, an additional full Sofa-bed ...
From $949 per night (USD)Expedia
From $679 per night (USD)VRBO
Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Your stay in this charming second-floor, two-bedroom, two-bath unit is made comfortable with all the essential ...
From $679 per night (USD)VRBO
From $349 per night (USD)Expedia
Island Inn - Studio Suite - 17D - Oak Bluffs, MA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This unit offers a bright, airy retreat with spacious interiors featuring two comfortable beds adorned with cr ...
From $349 per night (USD)Expedia
From $1457 per night (USD)VRBO
Steps to Inkwell Beach: Victorian Home!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
2,150 Sq Ft | Family Friendly | Walk to Shops, Restaurants, Ferry Terminal | Outdoor Shower & Grill It doesn't get any ...
From $1457 per night (USD)VRBO
From $490 per night (USD)Expedia
NEWLY RENOVATED! Quiet location, walk to Circuit Avenue and beaches!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your home away from home in Oak Bluffs with 4 bedrooms, including a ground floor bedroom and bath with zero-entry shower ...
From $490 per night (USD)Expedia
From $803 per night (USD)VRBO
Spacious island home near Farm Neck Golf Course, the beach and town
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Twin Ponds Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $803 per night (USD)VRBO
From $852 per night (USD)Expedia
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Come stay at our quaint Victorian cottage overlooking downtown Oak Bluffs and the Harbor, which are just a few blocks aw ...
From $852 per night (USD)Expedia
From $610 per night (USD)VRBO
4 Mi to Inkwell Beach: Home in Oak Bluffs!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
'Clark's Cove' | Idyllic Tree-Lined Surroundings | Outdoor Shower | 3 Mi to Ferry Terminal Your own slice of paradise a ...
From $610 per night (USD)VRBO
From $703 per night (USD)Expedia
3-bedroom house in charming Oak Bluffs with WiFi, AC. Start your vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Make yourself at home in this 3-bedroom Oak Bluffs retreat. This beautiful house features 2 king beds, 1 queen bed, a fu ...
From $703 per night (USD)Expedia
From $2090 per night (USD)VRBO
Welcome to your perfect island retreat nestled in a private Oak bluffs Enclave
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
This light filled modern, five ensuite bedrooms plus half bath home has everything you need for a perfect getaway. On t ...
From $2090 per night (USD)VRBO
From $893 per night (USD)VRBO
Charming 3BR Vineyard Retreat, Lg Deck w/ Kitchen, Near Beach, Town Ctr & Ferry
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to RoBree Farm – Your Martha’s Vineyard Retreat in the Heart of Oak Bluffs Escape to the serenity and magic of ...
From $893 per night (USD)VRBO
From $816 per night (USD)VRBO
Charming home with walkable beach, large yard, deck, fire pit, and A/C
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $816 per night (USD)VRBO
From $1006 per night (USD)VRBO
EXQUISITE MARTHA'S VINEYARD HOME, HEATED POOL, 10 MIN WALK TO OAK BLUFFS FERRY
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with v ...
From $1006 per night (USD)VRBO
From $752 per night (USD)VRBO
Charming 3-bedroom cottage in Oak Bluffs with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this renovated 3-bedroom home in Oak Bluffs, across from Farm Neck Golf Club. The Beach is just a 4-minute dri ...
From $752 per night (USD)VRBO
From $855 per night (USD)VRBO
Exquisitely Comfortable 4bdrm 3ba Home w/ Large Yard in Oak Bluffs!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Gloria’s Cottage – A Martha’s Vineyard Retreat Step into the warmth of Gloria’s Cottage, a beautifully appoi ...
From $855 per night (USD)VRBO
From $1127 per night (USD)VRBO
Updated 3-bedroom in gorgeous Oak Bluffs w/ waterviews and expansive front porch
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Get ready to relax in this 3-bedroom cottage in Oak Bluffs. Nestled in a peaceful neighborhood, this beautiful property ...
From $1127 per night (USD)VRBO
From $1617 per night (USD)VRBO
Cozy Oak Bluffs Cottage walk to town Pet Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This modest single-family home was newly renovated in 2023. It is a single-level house just west of downtown Oak Bluffs. ...
From $1617 per night (USD)VRBO
From $465 per night (USD)VRBO
Martha’s Vineyard 15 minute walk to Oak Bluffs Beach and Town
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
15 minute walk to Oak Bluffs town and beach. 2 queen beds. 5 minute walk to the bus. 5 minute walk to library. 1 bedroom ...
From $465 per night (USD)VRBO
From $1781 per night (USD)VRBO
Waterview Farm Contemporary Island Home Walk to Beach and Farm Neck Golf Club
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Six bedroom, five and a half bath contemporary island home located in Waterview Farm with direct access to the beach on ...
From $1781 per night (USD)VRBO
From $1137 per night (USD)VRBO
Retreat to Martha's Vineyard with a Private Pool & Outdoor Living in Oak Bluffs\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Retreat to Martha's Vineyard in a modern ranch style vacation home with a heated pool tucked on 1.5 acres of landscaped ...
From $1137 per night (USD)VRBO
From $1061 per night (USD)VRBO
Newly Renovated! Walk to Town Oak Bluffs, 4 Bedroom/3 Bath A/C
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This newly renovated home is approximately 2100sf with 4 bedrooms and 3 bathrooms. Furnished and decorated by award winn ...
From $1061 per night (USD)VRBO
From $369 per night (USD)VRBO
Downtown Oak Bluffs, short walk to beach & town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Location, location, location. This cozy 3 bedroom house is located steps from downtown on a family neighborhood side str ...
From $369 per night (USD)VRBO
Click For PricingVRBO
Three Bedroom Family Getaway in Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 6
Our Sweet Carol Lane home here on Martha's Vineyard is in a quiet neighborhood just over one mile away from the heart of ...
Click For PricingVRBO
From $488 per night (USD)VRBO
The Island Collection MV: Charming Cottage Located In Heart Of Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away ...
From $488 per night (USD)VRBO
From $442 per night (USD)VRBO
Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the desirable, private Meadow View Farms Estates, across from the Farm Neck Golf Club, this charmingly decora ...
From $442 per night (USD)VRBO
From $438 per night (USD)VRBO
Serene Sengekontacket Pond Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The property is set among several private townhouses in a lovely neighborhood located off of Sengekontacket Pond in Oa ...
From $438 per night (USD)VRBO
From $783 per night (USD)Expedia
Spacious Home - 1500 ft from Beach & Circuit Ave
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated four bedroom, two full bathroom home with an inviting front porch, private backyard and footsteps to Ci ...
From $783 per night (USD)Expedia
From $606 per night (USD)VRBO
Within Walking Distance to Town, Beach & Parks, Enclosed yard with a new deck,
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Located on historic Circuit Ave in Oak Bluffs within walking distance to town, beach, tennis courts and parks. Minutes a ...
From $606 per night (USD)VRBO
From $695 per night (USD)VRBO
Great location, happy house 0.5 mile Nancy’s & Jetty Beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
1900's Victorian, renovated and newly furnished. House is located on New York Ave, which is the main road between Oak Bl ...
From $695 per night (USD)VRBO
From $581 per night (USD)VRBO
Adorable Oak Bluffs Cottage With Ac On East Chop
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Adorable 4 bedroom cottage in the East Chop neighborhood of Oak Bluffs. You will love the beautiful back yard that has a ...
From $581 per night (USD)VRBO
From $685 per night (USD)VRBO
Beach, Town, Tennis, Pickleball - Central AC
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 15
We will let the photos do the talking, but note that this home has some especially attractive features for large groups, ...
From $685 per night (USD)VRBO
From $452 per night (USD)VRBO
Your \"Vineyard Dream\" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A BEAUTIFUL PROPERTY CLOSE TO TOWN-GREAT PRICE! LOTS OF PRIVACY BUT CLOSE TO EVERYTHING IN OB. ONE WEEK MINIMUM FOR ALL ...
From $452 per night (USD)VRBO
From $1228 per night (USD)VRBO
4 BR/4 BA Modern Victorian: The Mack on Winemack
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful Victorian home has all the charm of a true Martha’s Vineyard Gingerbread cottage combined with all of the ...
From $1228 per night (USD)VRBO
From $1331 per night (USD)VRBO
Oceanfront Home - Walk to Everything
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Endless water views, fully updated, and steps from a sandy beach excellent for swimming ("Inkwell"/Oak Bluffs Town Beach ...
From $1331 per night (USD)VRBO
From $399 per night (USD)VRBO
The Nest, Comfortable, Cozy and Convenient
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Nest is a private entranced guesthouse that is ideally located 2/3-1 mile walking distance to Oak Bluffs town, har ...
From $399 per night (USD)VRBO
From $795 per night (USD)VRBO
Beach and downtown OB walkable! 5 Bedroom Victorian on the park.
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 11
You will find this 5 Bedroom Victorian quite charming with its bright & cheery interior. Located right across from wide ...
From $795 per night (USD)VRBO
From $872 per night (USD)VRBO
The Island Collection MV: Experience a Luxury Getaway by the Lagoon
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful 3 bedroom home is located in a quiet area on Martha’s Vineyard by Lagoon Pond. When you walk inside, you ...
From $872 per night (USD)VRBO
From $776 per night (USD)VRBO
Beautiful MV Retreat - Central AC - Large Deck, Blue Stone Patio and Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Martha's Vineyard! Many of our guests return year after year, drawn by our property’s prime location, cleanli ...
From $776 per night (USD)VRBO
From $1876 per night (USD)VRBO
Modern Vineyard Home with Pool, Hot Tub and Pond
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
This is a great home for large families and friends. Amazing amenities include a brand new swimming pool, outdoor shower ...
From $1876 per night (USD)VRBO
From $1016 per night (USD)VRBO
Luxurious Sengekontacket Contemporary With Water Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
POINT B EXCLUSIVE - This freshly renovated Luxurious Contemporary combines water views out to Sengekontacket Pond from m ...
From $1016 per night (USD)VRBO
From $847 per night (USD)VRBO
Magnificent Spacious Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This lovely and beautifully furnished three-story home is located in a quiet residential section of Oak Bluffs. It is a ...
From $847 per night (USD)VRBO
From $1449 per night (USD)VRBO
Amazing Gem with Guest House and Private Sandy Beach on Lagoon Pond
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Nestled on a quiet road within walking distance to Oak Bluffs, this 3-bedroom house with a separate 1-bedroom guest hou ...
From $1449 per night (USD)VRBO
From $317 per night (USD)VRBO
The Sweetest Suite – Beach, kayaks & Starry Nights
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your perfect island escape. Tucked beneath a canopy of soaring 70-foot trees, our charming guest suite offers ...
From $317 per night (USD)VRBO
From $1709 per night (USD)VRBO
Spectacular Classic Waterfront Cottage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
33 Beach captures the essence of Martha's Vineyard. Built around the turn of the century as a stop for the New York Yach ...
From $1709 per night (USD)VRBO
From $987 per night (USD)VRBO
PRIVATE WATER ACCESS! ON FARM NECK GOLF COURSE! Kayaks & Canoe & A/C
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Immaculately clean, beautifully furnished three bedroom, 2 and 1/2 bath beach house in private community. Community is ...
From $987 per night (USD)VRBO
From $957 per night (USD)VRBO
Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to the Oak Bluffs Victorian Cottage that dreams are made of! Newly renovated (summer 2017), the rambling Main H ...
From $957 per night (USD)VRBO
From $681 per night (USD)VRBO
Beautiful home with pool in great location- close to everything!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedroom home with 2 big full bathrooms. Walk to ferry and town center. One of the bathrooms include a jacuzzi tub and ...
From $681 per night (USD)VRBO
From $841 per night (USD)VRBO
Ellen's MV Hideaway: Down island convenience, solitude, and lots of space!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
DM me before booking! Ellen’s Hideaway is an impeccably renovated home offering quality, beauty, and comfort, a welcomin ...
From $841 per night (USD)VRBO
From $1193 per night (USD)VRBO
Coastal Farmhouse With Connected Carriage House
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
POINT B EXCLUSIVE - This newly built Farmhouse with Connected Carriage House features a modern coastal-style with nice i ...
From $1193 per night (USD)VRBO
From $985 per night (USD)VRBO
Modern Farmhouse In Central Oak Bluffs Neighborhood
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
POINT B EXCLUSIVE - This newly-built Modern Farmhouse is tucked away in a quiet and centrally located neighborhood in Oa ...
From $985 per night (USD)VRBO
From $2158 per night (USD)VRBO
Grand Coastal-Style Estate In The Preserve
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 12
**AUGUST SPECIAL: SAVE $4,000 OFF 8/24 - 8/31 | NEW RATES PROGRAMMED** POINT B EXCLUSIVE - This recently built luxury ho ...
From $2158 per night (USD)VRBO
From $1035 per night (USD)VRBO
BRAND NEW!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful, brand new 5 BR, 2.5 BA w/ outdoor shower Cape-Style Home on 1 Acre of land minutes away from downtown Oak Blu ...
From $1035 per night (USD)VRBO
From $475 per night (USD)VRBO
4 bedroom home family friendly in desirable area
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This 4 bedroom, 3-story home has plenty of space to relax with two decks and a private third level master suite. Located ...
From $475 per night (USD)VRBO
From $851 per night (USD)VRBO
Close to Lagoon & easy access downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming, newly built home will provide the perfect getaway for your Martha's Vineyard vacation! Centrally-located, ...
From $851 per night (USD)VRBO
From $447 per night (USD)VRBO
Please let us know in advance which ferry you’re on and arrival time.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Fully equipped cottage behind the main house, Private, available all year round! Perfect romantic get away. Back Patio ...
From $447 per night (USD)VRBO
From $459 per night (USD)VRBO
Brick Ranch on Cul-de-sac, with Fireplace and Central Air Conditioning !
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom brick ranch at the end of a wooded cul-de-sac. Landscaped property located 1 mile from the town of Vineyar ...
From $459 per night (USD)VRBO
From $638 per night (USD)VRBO
Island Serenity: Beautiful home in quiet neighborhood close to Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely 3 bedroom, 2 full bathroom home with huge deck is less than 1 mile walk to famous Circuit Avenue in Oak Bluffs an ...
From $638 per night (USD)VRBO
From $471 per night (USD)VRBO
Charming Studio Guest House in the Heart of Oak Bluffs
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This recently renovated charming studio guest house in the heart of Oak Bluffs sleeps 2 in a Queen size bed. Complete w ...
From $471 per night (USD)VRBO
From $1685 per night (USD)VRBO
The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away ...
From $1685 per night (USD)VRBO
From $1457 per night (USD)VRBO
Discount last week July Reduced Oak Bluffs walk to Circuit Ave & Inkwell Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Surround yourself with comfort and fresh furnishings! This is a beautiful five-year-old home that is stylishly furnishe ...
From $1457 per night (USD)VRBO
From $1023 per night (USD)VRBO
Now booking Summer 2026!! OAK BLUFFS 5 Bedroom/3 Bath/Central AC.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This is one summer school you won't want to miss! Bright, airy, elegant home is perfect combination of past and present ...
From $1023 per night (USD)VRBO
From $458 per night (USD)VRBO
ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Gorgeous newly renovated and newly furnished mid-century beach cottage designed by prominent interior design firm Tersig ...
From $458 per night (USD)VRBO
From $563 per night (USD)VRBO
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Extra-large gingerbread cottage in historic Campgrounds in Oak Bluffs, sleeps nine. Located on a double lot in the hear ...
From $563 per night (USD)VRBO
From $335 per night (USD)VRBO
Sweet Little Post&Beam
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Very comfortable well appointed 750 sq ft home with heat and AC. Has 1 bedroom upstairs with a queen size bed and a hal ...
From $335 per night (USD)VRBO
From $418 per night (USD)VRBO
Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
If Steamship Authority ferry reservations appear to be unavailable, please contact me for possible options. Please not ...
From $418 per night (USD)VRBO
From $1192 per night (USD)VRBO
Original Pratt House built in 1866 with Ocean View of the Inkwell beach.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was ...
From $1192 per night (USD)VRBO
From $659 per night (USD)VRBO
OAK BLUFFS - INKWELL WATERVIEW Renovated Cottage with A/C, modern decor
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautifully renovated in-town Victorian Cottage. 4 bedrooms and 2.5 baths. 2 of the 4 bedrooms with a partial water view ...
From $659 per night (USD)VRBO
From $2498 per night (USD)VRBO
East Chop Beach House w/Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Fabulous new house in East Chop completed in 2019 located in the heart of East Chop. The house is well appointed, very ...
From $2498 per night (USD)VRBO
From $335 per night (USD)VRBO
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Tucked in a quiet neighborhood and within walking distance to town and beaches, this quaint cottage was moved to East Ch ...
From $335 per night (USD)VRBO
From $1181 per night (USD)VRBO
Modern Martha's Vineyard Retreat in Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
New construction home in Oak Bluffs. Enjoy a modern, clean and peaceful stay in the Vineyard. This home is mins to dow ...
From $1181 per night (USD)VRBO
From $423 per night (USD)Expedia
Conveniently located near Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This comfortable home has all the amenities of home in an idyllic setting, easy access to town, beach and gorgeous East ...
From $423 per night (USD)Expedia
From $1399 per night (USD)VRBO
Best Kept Secret Retreat for Adults with Water & Golf Course Views!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
Quite, serene, tranquil & beautiful are words guests have used to describe this home. This newly renovated home provide ...
From $1399 per night (USD)VRBO
From $452 per night (USD)VRBO
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 6
Mid-century rustic cottage charm tucked on 3 acres 1 mi to Oak Bluffs and Vineyard Haven center's. Acquired in 1950 by L ...
From $452 per night (USD)VRBO
From $1376 per night (USD)VRBO
Walk to Beach and Town. Large Family House.
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
-Seven air conditioned bedrooms -Four bathrooms -One living room and two small sitting rooms -large bluestone patio wit ...
From $1376 per night (USD)VRBO
From $663 per night (USD)VRBO
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! Deck,A/C,Outdoor Shower, Wifi
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $663 per night (USD)VRBO
From $435 per night (USD)VRBO
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
quaint quite modern but rustic guest house ideal for couple far from crowds but close to all located in oak bluffs 4 mi ...
From $435 per night (USD)VRBO
From $560 per night (USD)VRBO
Oak Bluffs Cottage - A Short Walk to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay in this beautiful Vineyard home and enjoy a relaxing vacation back in time! Within 5 minutes of stepping out the f ...
From $560 per night (USD)VRBO
From $525 per night (USD)VRBO
Water View Oasis 1 mi from Oak Bluffs 10 min Walk to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful water view, spacious natural landscape, and privacy enhance the serenity of our rustic barn-style home tucked ...
From $525 per night (USD)VRBO
From $643 per night (USD)VRBO
Convenient In-Town (Oak Bluffs) Location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great Vineyard location on Vineyard Avenue in Oak Bluffs. Built in 1920 and thoughtfully restored in 1999, this house is ...
From $643 per night (USD)VRBO
From $346 per night (USD)VRBO
In-Town Certified National Historic Oak Bluffs Property -
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the ...
From $346 per night (USD)VRBO
From $547 per night (USD)VRBO
Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This comfortable house provides up and downstairs amenities. The master bedroom with bath is on the ground floor; the o ...
From $547 per night (USD)VRBO
From $1117 per night (USD)VRBO
Waterfront Home in Oak Bluffs - Walk to Town and Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This lovely four-bedroom shingled Cape overlooks Farm Pond, Harthaven, and Nantucket Sound. It is a vintage cottage com ...
From $1117 per night (USD)VRBO
From $489 per night (USD)VRBO
Close to town, beautifully updated
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
*** For stays between 9/1/2024 and 6/14/2025, Please inquire about a discounted cleaning rate***. Renovated Oak Blu ...
From $489 per night (USD)VRBO
From $454 per night (USD)VRBO
Comfortable Island Home, Easy Access to Beaches and Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Salt Box style Log Home with open floor plan built by my family with a country feel, located on a wooded lot in the down ...
From $454 per night (USD)VRBO
From $492 per night (USD)VRBO
Delilah & Joseph Pierce House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Travel and Enjoy! Built by international artist, curator, educator, advocate, and diplomat Delilah W. Pierce, and her fa ...
From $492 per night (USD)VRBO
From $767 per night (USD)VRBO
Dog-friendly home with fenced yard- walking distance to beach, ferry & town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Wayland Victorian Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $767 per night (USD)VRBO
From $718 per night (USD)VRBO
Completely renovated, air conditioned cottage close to the beach. Dog friendly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This property has something for the whole family to enjoy. A large wrap-around porch, screened in dining area on side po ...
From $718 per night (USD)VRBO
From $567 per night (USD)VRBO
Location, Charm, & Steps to Town/Beach -- Central AC, 100% Renewable Energy
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
(Note: for 2025, we are renovating the upstairs bath and creating a more spa-like shower. New Photos by late March, rou ...
From $567 per night (USD)VRBO
From $4032 per night (USD)VRBO
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
6 Bedrooms, Sleeping Porch, 3 Full Baths, 2 Half Baths, Sleeps 12+ A timeless Martha’s Vineyard escape awaits you at th ...
From $4032 per night (USD)VRBO