Oak Bluffs, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Oak Bluffs, Massachusetts on RentalSaver.com!

Oak Bluffs Rentals

From $411 per night (USD)
VRBO
Quiet 2-Bed, 2-Bath Condo with Spacious Sundeck & Tennis Courts
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a peaceful retreat in this cozy 2-bedroom, 2-bath condo with air conditioning, offering the perfect space to relax ...
From $411 per night (USD)
VRBO
From $1248 per night (USD)
VRBO
Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
THE “SUMMER WIND” HOUSE - WALK TO EVERYTHING! We have completely renovated our 5-bedroom, 3-full bathroom home with cent ...
From $1248 per night (USD)
VRBO
From $1416 per night (USD)
VRBO
Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Newly renovated luxury home with 2 king sized en suites and heated pool & hot tub is centrally located! 1.5 miles to dow ...
From $1416 per night (USD)
VRBO
From $1167 per night (USD)
VRBO
AMENITIES GALORE IN OAK BLUFFS PRIVATE COMMUNITY, DOCK, TENNIS, CENTRAL AC
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Our wonderful vacation home has been renovated adding central AC, new carpeting, new quartz countertops in both kitchens ...
From $1167 per night (USD)
VRBO
From $535 per night (USD)
VRBO
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Welcome to "Eventide." Your historic vacation home is nestled at 63 Temahigan Ave. in Oak Bluffs- Martha's Vineyard. Con ...
From $535 per night (USD)
VRBO
From $702 per night (USD)
Expedia
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Renovated in 2022, The Panola House is tucked away on a private expansive lot with its own roundabout driveway. The prop ...
From $702 per night (USD)
Expedia
From $489 per night (USD)
VRBO
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Bedrooms:
0
Bathrooms:
3
Sleeps:
6
Family owned and kept charming 19th century home in Oak Bluffs highlands near Baptist Temple park. This house is about ...
From $489 per night (USD)
VRBO
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Expedia
Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w/AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our location is the best of both worlds! The house is quietly situated among pine trees with few neighbors, plus it is w ...
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Expedia
From $650 per night (USD)
VRBO
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation ...
From $650 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Cozy cottage 3/4 mile from Oak Bluffs harbor
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Family owned/charming home in Oak Bluffs, 1/2 mile walk to East Chop Lighthouse and slightly more to the town harbor, wh ...
From $367 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience the charm of Martha’s Vineyard at your leisure from this ideally located apartment. With 2 bedrooms and 1 bat ...
From $515 per night (USD)
VRBO
From $638 per night (USD)
Expedia
Quaint,,,Quiet..up island feel yet a short walk to town and harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Your quintessential summer vacation starts here! The property has a combination of a strong rental history(read ren ...
From $638 per night (USD)
Expedia
From $853 per night (USD)
VRBO
Beautiful downtown Oak Bluffs!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Beautifully decorated ranch style home in Oak Bluffs Center. Close to the beach, restaurants, shopping, parks, library a ...
From $853 per night (USD)
VRBO
From $715 per night (USD)
VRBO
Perfect Family Home- Oak Bluffs, Martha's Vineyard
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Our wonderful family house is exactly what you're looking for to compliment your Martha's Vineyard vacation. The house' ...
From $715 per night (USD)
VRBO
From $536 per night (USD)
VRBO
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity, ...
From $536 per night (USD)
VRBO
From $536 per night (USD)
Expedia
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity ...
From $536 per night (USD)
Expedia
From $622 per night (USD)
VRBO
Peaceful Oak Bluffs home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax and pamper yourself kin a Mid-Century Modern Split-Level home. Located on a 1/4 acre lot minutes away from town,b ...
From $622 per night (USD)
VRBO
From $714 per night (USD)
Expedia
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Introducing our #CozyBluffs home in Oak Bluffs on Martha's Vineyard! Designed by local Architect Chuck Sullivan and buil ...
From $714 per night (USD)
Expedia
From $2324 per night (USD)
VRBO
Beautiful 5 BR, 4.5 baths w/ modern conveniences
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
We welcome you to enjoy our spacious and comfortable home. It's a beautiful 5 BR, 4.5 bath Oak Bluffs home with modern ...
From $2324 per night (USD)
VRBO
Click For Pricing
Expedia
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC
Bedrooms:
2
Bathrooms:
7
Sleeps:
10
The cottage is in restored original condition with many original features including hardwood floors, paned windows with ...
Click For Pricing
Expedia
From $372 per night (USD)
VRBO
Family Fun, Spacious+Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
About this space Welcome to the Burkeshire Manor! Enjoy the breeze of fresh air of the countryside from the shaded patio ...
From $372 per night (USD)
VRBO
From $920 per night (USD)
Expedia
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This lovely, spacious, and beautifully appointed condo is just steps from the beach and a short walk to the heart of Oak ...
From $920 per night (USD)
Expedia
From $880 per night (USD)
VRBO
Oak Bluffs - Quiet Neighborhood - Walk to Town, Ferry, Library and more!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This property is situated in a quiet neighborhood just a short walk to downtown Oak Bluffs. This location is perfect. ...
From $880 per night (USD)
VRBO
From $431 per night (USD)
Expedia
Cozy Beach Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Newly refurbished Cottage City Victorian beach house, built in 1870. Walk to beach, walk to town. 2 bedrooms up a narro ...
From $431 per night (USD)
Expedia
From $1833 per night (USD)
VRBO
Soulas Martha's Vineyard, Walk to Inkwell Beach & Town
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Newly renovated, Great for Family & Friend Stays, Corporate Retreats, Central Air & Heat, walk to Circuit Ave and Beach, ...
From $1833 per night (USD)
VRBO
From $1467 per night (USD)
VRBO
Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch.
Bedrooms:
2
Bathrooms:
6
Sleeps:
13
*** CONTACT HOST TO CONFIRM DATES BEFORE BOOKING**** *** CONTACT HOST FOR EARLY BIRD SPECIAL AND OFF-SEASON RATES*** * ...
From $1467 per night (USD)
VRBO
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VRBO
4+ Bedroom. Great location. Meadow View Rd. Oak Bluffs.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This spacious, well-decorated home is located in Meadow View Farms, Oak Bluffs - a quiet neighborhood of gracious custom ...
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VRBO
From $619 per night (USD)
Expedia
Beautiful 3 bedroom 2 bath Home / Close to Town & Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful and spacious 3 bedroom and 2 bathroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape style home. ...
From $619 per night (USD)
Expedia
From $595 per night (USD)
VRBO
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This home has all the amenities to make your stay a comfortable one. Its character stems from being built in the 1920s w ...
From $595 per night (USD)
VRBO
From $1104 per night (USD)
Expedia
Beautiful Carriage House on the Chop
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Recently built, this spectacular 3 Bedroom carriage house is located on 3/4 acre estate on beautiful East Chop Drive. Th ...
From $1104 per night (USD)
Expedia
From $628 per night (USD)
VRBO
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
A comfortable residence, this charming ranch has all the amenities for a perfect vacation. It's quiet location is 1.5 mi ...
From $628 per night (USD)
VRBO
Click For Pricing
Expedia
1 Bedroom, Sleeps 4; perfect small family vacation home
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Close to town and beach, but far enough away for peaceful quiet. 1 Bedroom; 3.5 bath; outdoor shower; front and side por ...
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Expedia
$Welcome to \Suzy's Place\ Best Location! Walk Everywhere. Newly built in 2024.$
From $847 per night (USD)
VRBO
Welcome to \"Suzy's Place\" Best Location! Walk Everywhere. Newly built in 2024.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
"Suzy's Place" is arguably the best location on the island. Your cozy getaway awaits in Oak Bluffs at this beautiful new ...
From $847 per night (USD)
VRBO
From $957 per night (USD)
Expedia
Brand New Guest house
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in Oak Bluffs, enjoy what this 2-bedroom apartment has to offer. With a washing machine, WiFi, AC, iron, hair dr ...
From $957 per night (USD)
Expedia
From $529 per night (USD)
VRBO
BRAND NEW 1-bedroom Owner's Suite in wonderful Oak Bluffs with Air Conditioning
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Get ready to relax in this 1-bedroom Owner's Suite in Oak Bluffs. This brand new property features a cozy bedroom with a ...
From $529 per night (USD)
VRBO
From $556 per night (USD)
Expedia
Spacious Second FL 4-Bedroom Rental – Private Entrance & Newly Renovated Deck!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Spacious 4-Bedroom Rental in Oak Bluffs – Private Entrance & Newly Renovated Deck! Enjoy the best of Oak Bluffs in this ...
From $556 per night (USD)
Expedia
From $894 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 $894 per night (USD)
VRBO
From $1184 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 $1184 per night (USD)
Expedia
From $693 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 $693 per night (USD)
VRBO
From $922 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 $922 per night (USD)
VRBO
From $891 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 $891 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Walk to Ferry & Beach from Central Oak Bluffs
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 3A Circuit Breeze The Space: Welcome to Circuit Breeze, a bright and comfortable first-floor retreat desig ...
From $669 per night (USD)
Expedia
From $1216 per night (USD)
VRBO
Relax & Unwind: Poolside Martha’s Vineyard Stay
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Luxury Vineyard Haven Home w/ Pool & Game Room Vineyard Haven Luxury Retreat with Pool, Foosball & Central Location We ...
From $1216 per night (USD)
VRBO
From $430 per night (USD)
Expedia
Oak Bluffs home conveniently located.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Plan your escape to Martha's Vineyard! Conveniently located near downtown Oak Bluffs, this 2BD/2BA home provides easy ac ...
From $430 per night (USD)
Expedia
From $5393 per night (USD)
VRBO
The Ultimate Group Escape on Marthas Vineyard
Bedrooms:
3
Bathrooms:
6
Sleeps:
18
Summary: Circuit Breeze, Sand By Me & Whale Tail Retreat The Space: Experience the ultimate Martha’s Vineyard getaw ...
From $5393 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
Family Friendly Hidden Oaks Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Located a short stroll away from Oak Bluffs harbor (and a 10-minute drive to the town beach), this serene home is centra ...
From $1181 per night (USD)
Expedia
From $1015 per night (USD)
VRBO
Charming 1-bedroom bungalow with AC in Oak Bluffs
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Stay comfortably in Oak Bluffs at this newly built delightful 1-bedroom bungalow. The bedroom features a cozy queen bed, ...
From $1015 per night (USD)
VRBO
From $827 per night (USD)
Expedia
4 bedroom cottage in Oak Bluffs Martha's Vineyard
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Nestled in Oak Bluffs, this delightful cottage offers 4 bedrooms - 3 with queen beds, one with 2 twin beds, With 2 bathr ...
From $827 per night (USD)
Expedia
From $891 per night (USD)
VRBO
Wayland Victorian in Oak Bluffs
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Wayland Victorian in Oak Bluffs Victorian Charm in Oak Bluffs – Walk to Beaches & Harbor Enjoy one of the best spots o ...
From $891 per night (USD)
VRBO
From $628 per night (USD)
Expedia
Family Home Near Arts District & Inkwell Beach
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Family Home Near Arts District & Inkwell Beach Family-Friendly Home with Backyard – 1 Mile to Beach Bring the whole fa ...
From $628 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 $1042 per night (USD)
Expedia
Spacious island home near Farm Neck Golf Course, the beach and town
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Twin Ponds The Space: Nestled just a stone's throw away from the renowned Farm Neck golf course in Oak Blu ...
From $1042 per night (USD)
Expedia
From $502 per night (USD)
VRBO
Quaint, ranch style home in Oak Bluffs with central air
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: The Rootskeller The Space: Nestled at the end of a tranquil cul de sac, this charming cabin-style home in ...
From $502 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Family friendly, walking distance to town, harbor, shops, restaurants, beaches
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Summary: Canary Cottage The Space: Experience the Martha's Vineyard of yesteryear at this beautifully updated histo ...
From $586 per night (USD)
Expedia
From $705 per night (USD)
VRBO
Inviting, two-story home with a large yard, sunroom, balcony
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Gingerbread Dream The Space: Experience the laidback lifestyle of the Vineyard from this classic, two-stor ...
From $705 per night (USD)
VRBO
From $810 per night (USD)
Expedia
Historical house with wraparound porch, modern updates, enclosed yard, & W/D
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Summary: Victorian by the Sea The Space: A unique coastal stay awaits you and yours at this newly renovated, grand ...
From $810 per night (USD)
Expedia
From $1087 per night (USD)
VRBO
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Summary: Bird Street Breeze The Space: Nestled in a quiet neighborhood next door to the public library (with access ...
From $1087 per night (USD)
VRBO
From $3152 per night (USD)
Expedia
2-story home near Crystal Lake with partial views, deck, grill, outdoor shower
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Summary: Vineyard State of Mind The Space: Centrally located within one and a half miles of downtown Oak Bluffs, th ...
From $3152 per night (USD)
Expedia
From $724 per night (USD)
VRBO
Updated house close to town and beach with patio, AC, and games
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Summary: Sankofa House The Space: Nestled in the historic Vineyard Highlands at the beginning of the African Americ ...
From $724 per night (USD)
VRBO
From $1069 per night (USD)
Expedia
Private island house with close beach access and water view from deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Summary: Soundmeadow House The Space: Located just outside the charming town of Oak Bluffs, MA, this delightful hou ...
From $1069 per night (USD)
Expedia
From $1027 per night (USD)
VRBO
House with guest studio close to town and beach with grill, games, AC & patio
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: Sankofa Martha's Vineyard The Space: Nestled in the historic Vineyard Highlands at the beginning of the Af ...
From $1027 per night (USD)
VRBO
From $727 per night (USD)
Expedia
Charming Martha's Vineyard retreat close to beaches & downtown - large yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Set Sail The Space: Set, sail, and settle down at this charming Martha's Vineyard hideaway! Showcasing one ...
From $727 per night (USD)
Expedia
From $1340 per night (USD)
VRBO
Charming home with private hot tub, firepit, deck, grill, outdoor shower, AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Tiffany's Treasure The Space: This two-story home will be just the perfect place to bring the whole family ...
From $1340 per night (USD)
VRBO
From $1200 per night (USD)
Expedia
Charming home near downtown & beach with patio, outdoor shower, grill, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Blissful Island Haven The Space: Centrally located within a half-mile of Inkwell Beach and a mile of downt ...
From $1200 per night (USD)
Expedia
From $311 per night (USD)
VRBO
Stylish island retreat with sunny interiors, wraparound deck, firepit & AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Fresh Pond Chateau The Space: Welcome to Fresh Pond Chateau, a beautifully renovated cottage nestled on a ...
From $311 per night (USD)
VRBO
From $838 per night (USD)
Expedia
Spacious colonial home close to town with AC, porches, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Seabreeze Retreat The Space: Welcome to your perfect summer retreat in Oak Bluffs, MA! This charming house ...
From $838 per night (USD)
Expedia
From $1102 per night (USD)
VRBO
Historic, dog-friendly beach view house with fast WiFi, ocean view, & grill
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
Summary: Captain Shaw Norris House The Space: Don't miss your chance to book this incredible historic beach view ho ...
From $1102 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
Enchanting home with tennis, firepit, golf nearby & washer/dryer
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Summary: Bird's Paradise The Space: Find serenity on the coastal bay of Martha's Vineyard with this fantastic getaw ...
From $1000 per night (USD)
Expedia
From $681 per night (USD)
VRBO
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Sunset Meadows The Space: The stunning waterways and marshlands of Martha's Vineyard are just outside your ...
From $681 per night (USD)
VRBO
From $700 per night (USD)
Expedia
Oak Bluffs Home with Renovated Screened-in Porch - Short Drive to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Fallen Oak Retreat The Space: Located in the historic Oak Bluffs neighborhood, this recently remodeled 3BR ...
From $700 per night (USD)
Expedia
From $468 per night (USD)
VRBO
Bright old-world cottage with two porches & large yard - walk to town & beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Oak Bluffs Cottage The Space: Savor the old-world charms of Oak Bluffs Cottage, an ideally situated Martha ...
From $468 per night (USD)
VRBO
From $783 per night (USD)
Expedia
Cozy island cottage near local attractions with breezy yard & inviting interior
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: TumbleINN The Space: Welcome to your ideal island retreat in Oak Bluffs, where unforgettable family vacati ...
From $783 per night (USD)
Expedia
From $1584 per night (USD)
VRBO
Private house with jetted tub, deck, grill, central AC and large yard
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Family Getaway The Space: Welcome to your perfect getaway in Oak Bluffs, MA! This charming house offers a ...
From $1584 per night (USD)
VRBO
From $1060 per night (USD)
Expedia
Historic cottage with patio, games, walk to beach & dog-friendly fenced yard
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Summary: Pilgrim Cottage The Space: Welcome to Pilgrim Cottage, your cozy home base for an authentic Martha’s Viney ...
From $1060 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Coastal home with outdoor shower, grill, fireplace, central AC, & W/D
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Yellow Brick Road House The Space: Bright and inviting, this home provides an ideal escape for your family ...
From $389 per night (USD)
VRBO
From $478 per night (USD)
Expedia
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Summary: Winthrop Cottage The Space: If you are planning a family vacation to Martha's Vineyard, consider this affo ...
From $478 per night (USD)
Expedia
From $1028 per night (USD)
VRBO
Newly remodeled home w/ new furniture, large yard & great porches
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Sunny Side Up The Space: Freshly remodeled with brand new furnishings throughout, this Oak Bluffs home is ...
From $1028 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Cozy getaway in a central location w/ a full kitchen & furnished deck
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Sea Glen Cottage The Space: This lovely cottage awaits you for your next Martha's Vineyard getaway with th ...
From $358 per night (USD)
Expedia
From $616 per night (USD)
VRBO
New Construction with Patio & Yard - Downtown & Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Oak Bluffs Beauty The Space: Immerse yourself in the charms of Oak Bluffs at this Martha's Vineyard home, ...
From $616 per night (USD)
VRBO
From $1070 per night (USD)
Expedia
Elegant Dream Home w/ Luxurious Living Spaces, Full Kitchen, & Wraparound Porch
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Oak Manor The Space: Welcome to your dream getaway in the charming town of Oak Bluffs, MA! This delightful ...
From $1070 per night (USD)
Expedia
From $1880 per night (USD)
VRBO
Charming home with walkable beach, large yard, deck, fire pit, and A/C
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Summary: Beach House The Space: Nestled in a tranquil neighborhood of Oak Bluffs, this charming and spacious home o ...
From $1880 per night (USD)
VRBO
From $611 per night (USD)
Expedia
Private suite with roof deck, near golf, bus stop, shops, and trails
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Garage Suite The Space: Welcome to our cozy one-bedroom suite, a perfect retreat for couples or solo trave ...
From $611 per night (USD)
Expedia
From $1046 per night (USD)
VRBO
Serene private home w/ large deck & yard on conservation land
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Summary: The Big Easy The Space: Welcome to your perfect family getaway in Oak Bluffs, MA! Nestled on a serene cul- ...
From $1046 per night (USD)
VRBO
From $782 per night (USD)
Expedia
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)
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 $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 $1340 per night (USD)
VRBO
Historic Oak Bluffs Cottage – Porch with View
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Historic Oak Bluffs Cottage – Porch with View Step into the charm of a bygone era at this classic Oak Bluffs home, fill ...
From $1340 per night (USD)
VRBO
From $734 per night (USD)
Expedia
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)
Expedia
From $836 per night (USD)
VRBO
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)
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 $836 per night (USD)
VRBO
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)
VRBO
From $857 per night (USD)
Expedia
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)
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 $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 $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 $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 $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 $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

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Results: 293 Rentals