Oak Bluffs Rentals
From $634 per night (USD)VRBO
Charming Recently Renovated 3-Bedroom Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to our cozy home, ideally located just 1 mile from the ferry, within walking distance to the lagoon via a scenic ...
From $634 per night (USD)VRBO
From $592 per night (USD)Expedia
Renovated Vineyard Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming vacation retreat! This recently renovated cottage is perfect for a summer escape to the Vineyar ...
From $592 per night (USD)Expedia
From $1221 per night (USD)VRBO
Delightful and Roomy 4-bedroom house in OB, 4 bed, 4 bath, Central A/C
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Make yourself at home in this fabulous 4-bedroom Oak Bluffs retreat. With 3 queen beds, 2 twins, and 2 sofa beds, this a ...
From $1221 per night (USD)VRBO
From $868 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 $868 per night (USD)Expedia
From $633 per night (USD)VRBO
Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to your home away from home! Experience the charm of Oak Bluffs in this spacious 3-bedroom, 2.5-bathroom beautif ...
From $633 per night (USD)VRBO
From $790 per night (USD)Expedia
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 $790 per night (USD)Expedia
From $1023 per night (USD)VRBO
Vineyard Social-Spacious 5BR Home in Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fant ...
From $1023 per night (USD)VRBO
From $726 per night (USD)Expedia
Charming 3-bedroom w/loft.New Construction home with AC,WiFi. Short walk to town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Oak Bluffs home boasts 3 inviting bedrooms and a cozy loft, including 2 king beds, 2 full beds and a queen sofa bed ...
From $726 per night (USD)Expedia
From $677 per night (USD)VRBO
Quiet Getaway Within Walking Distance Of All Oak Bluffs Has To Offer.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
An enchanting Cape Cod cottage nestled on a quiet road with Farm Pond and ocean views. Share family dinners and conversa ...
From $677 per night (USD)VRBO
From $447 per night (USD)Expedia
Oak Bluffs 3-Bedroom Victorian Cottage, Steps from Sunset Lake/Park
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Step Into Vineyard history—with a modern twist. Originally part of the historic Methodist Campground in Oak Bluffs, this ...
From $447 per night (USD)Expedia
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Renovated Vineyard Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming vacation retreat! This recently renovated cottage is perfect for a summer escape to the Vineyar ...
Click For PricingVRBO
From $1468 per night (USD)VRBO
Waterfront home in Vineyard Haven. Walking distance to shops and dining.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This waterfront house is the perfect home base for your trip to Martha's Vineyard. A stay at this great location will pu ...
From $1468 per night (USD)VRBO
From $1005 per night (USD)VRBO
Breathtaking Waterviews with Private Beach - Harbour House with AC and Heat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Breathtaking views, with a short (2 minute) walk to the private beach and the most prestigious golf course on the island ...
From $1005 per night (USD)VRBO
From $449 per night (USD)VRBO
Updated Vineyard Farmhouse - Walk to Town & Ferry
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This well maintained, bright and cheery Vineyard farmhouse includes 4 bedrooms and 2.5 renovated bathrooms with outdoor ...
From $449 per night (USD)VRBO
From $476 per night (USD)VRBO
Charming Vineyard Classic Home, Walk to Town & Boat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a charming and comfortable stay in our Martha's Vineyard home, built in 1920 and recently updated with modern amen ...
From $476 per night (USD)VRBO
From $3483 per night (USD)VRBO
Spacious 9-bedroom house with Waterview, WiFi, AC in delightful Oak Bluffs
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 18
Get ready to relax in this 9-bedroom house in Oak Bluffs. This superb property boasts 3 king beds, 5 full beds, and 2 tw ...
From $3483 per night (USD)VRBO
From $1129 per night (USD)VRBO
Beautiful home with screened porch, deck, W/D, family room, & central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blissful Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $1129 per night (USD)VRBO
From $1118 per night (USD)Expedia
Waterfront Home w/ Guest Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the magic of Martha's Vineyard from our beachfront retreat. Nestled in a quiet neighborhood, yet conveniently ...
From $1118 per night (USD)Expedia
From $557 per night (USD)VRBO
Charming 3-Bedroom Home in the Heart of Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Martha’s Vineyard getaway! Nestled in the heart of Oak Bluffs, this charming 3-bedroom home offe ...
From $557 per night (USD)VRBO
From $719 per night (USD)VRBO
Lovely spacious MV 3-bdr, 3 bath island home, sleeps 12, air and comm. pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Make yourself at home in our lovely 3-bedroom West Tisbury retreat. Perfect for families and friends looking for a peace ...
From $719 per night (USD)VRBO
From $247 per night (USD)VRBO
2-bedroom house, Short walk to beach, with AC and WiFi in Oak Bluffs
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private Home and yard a block from the Lagoon in Oak Bluffs. Easy walk to quiet neighborhood beach. Brand new kitchen/ba ...
From $247 per night (USD)VRBO
From $1230 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 $1230 per night (USD)Expedia
From $3671 per night (USD)VRBO
WE’RE BACK! Oak Bluffs Retreat. NEW PRIVATE POOL -- FERRY TIX!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Large beautifully appointed three bedroom, 2 1/2 bath house, with a den perfect for space for everyone to enjoy themselv ...
From $3671 per night (USD)VRBO
From $571 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 $571 per night (USD)VRBO
From $720 per night (USD)VRBO
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 $720 per night (USD)VRBO
From $580 per night (USD)Expedia
Downtown brand new construction 3 bed & 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brand-new, high-end 3BR/3BA home in the heart of Vineyard Haven—just one block from the ferry terminal. Walk to restaura ...
From $580 per night (USD)Expedia
From $452 per night (USD)VRBO
Short Walk to Town - Nice Comfortable -Reasonable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This property is new to VRBO, however it has been hosting guests for several years on another site with 5 star reviews. ...
From $452 per night (USD)VRBO
From $1223 per night (USD)Expedia
Charming 3-bedroom family home with WiFi and AC in Vineyard Haven.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this family home with 3 bedrooms, a spacious loft with half bath, and comfortable amenities. This property has a l ...
From $1223 per night (USD)Expedia
From $776 per night (USD)VRBO
Completely Renovated Oak Bluffs Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Fully renovated for 2025, this stylish 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis cour ...
From $776 per night (USD)VRBO
From $1691 per night (USD)Expedia
6bedroom, 4bath, chefs kitchen, central air, ping pong, walking distance to town
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
This NEWLY RENOVATED 6-bedroom house in Vineyard Haven is just a 10 minute walk to public beach, downtown restaurants, b ...
From $1691 per night (USD)Expedia
From $1224 per night (USD)VRBO
Modern 4BR Escape w Jeep Wrangler. Near Town. Patio, Fire Pit & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your vacation retreat! This recently renovated single-family near downtown Vineyard Haven blends high-end fin ...
From $1224 per night (USD)VRBO
From $906 per night (USD)Expedia
Walk to town & beach A/C, Strong WiFi, family & pet friendly. Outdoor shower
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summertime! And the living is easy in this comfortable, casual home on Martha's Vineyard. The large front deck is great ...
From $906 per night (USD)Expedia
From $591 per night (USD)VRBO
Spacious colonial home close to town with AC, porches, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Seabreeze Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $591 per night (USD)VRBO
From $1452 per night (USD)Expedia
Stunning Tisbury Retreat with Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to this brand-new luxury home in Vineyard Haven, minutes from downtown and the ferry. Designed for comfort and st ...
From $1452 per night (USD)Expedia
From $311 per night (USD)VRBO
Quaint, ranch style home in Oak Bluffs with central air
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
The Rootskeller Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $311 per night (USD)VRBO
From $838 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 $838 per night (USD)VRBO
From $677 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 $677 per night (USD)VRBO
From $420 per night (USD)VRBO
Charming 2-bedroom townhouse in Oak Bluffs with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Sengekontacket pond in Oak Bluffs is waiting for you at this quiet 2-bedroom townhouse with a private deck overlooking a ...
From $420 per night (USD)VRBO
From $2066 per night (USD)VRBO
Spacious, Family-Friendly Edgartown Home – 3BR, Sleeps 14, Renovated in 2025
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Spacious & Family-Friendly Edgartown Retreat – Fully Renovated in 2025 Welcome to your perfect Martha’s Vineyard getawa ...
From $2066 per night (USD)VRBO
From $405 per night (USD)VRBO
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Dogs Welcome w/ Fee | Beach Across Street | Postcard-Worthy Sunsets Easy island living awaits at this 3-bedroom, 1-bath ...
From $405 per night (USD)VRBO
From $239 per night (USD)VRBO
Walk to Beach & Lighthouse: Oak Bluffs Studio!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Pets Welcome w/ Fee | Solo Getaway or Couple's Retreat Island charm meets laid-back comfort at this 1-bathroom studio i ...
From $239 per night (USD)VRBO
From $1078 per night (USD)Expedia
Private house with jetted tub, deck, grill, central AC and large yard
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Family Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1078 per night (USD)Expedia
From $429 per night (USD)VRBO
Private suite with roof deck, near golf, bus stop, shops, and trails
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Garage Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $429 per night (USD)VRBO
From $955 per night (USD)Expedia
Charming, Victorian in East Chop
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Relax with the whole family at this peaceful place to stay. Ideally located in East Chop, in walking distance to the B ...
From $955 per night (USD)Expedia
From $666 per night (USD)VRBO
Walk to Beach Spacious Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to our vineyard home, a charming haven nestled on 1/3 acre of land within steps to the center of town. This retre ...
From $666 per night (USD)VRBO
From $776 per night (USD)Expedia
Spacious house with private yard, firepit - option to rent car
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
3 Sisters Vineyard Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $776 per night (USD)Expedia
From $1132 per night (USD)VRBO
Wishing Well Oak Bluffs: 4-bedroom house with WiFi, AC - Close to Beach and Town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Consider this house your home away from home while you visit Oak Bluffs. With 4 charming bedrooms including a queen bed, ...
From $1132 per night (USD)VRBO
From $1068 per night (USD)Expedia
Serene private home w/ large deck & yard on conservation land
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
The Big Easy Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1068 per night (USD)Expedia
From $526 per night (USD)VRBO
Oasis in downtown Oak Bluffs: 2 x King BR Condo, AC & Prime Location, sleeps 6\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 'Whale Tail', one of the most iconic and talked-about properties in Oak Bluffs! Located directly above Vineya ...
From $526 per night (USD)VRBO
From $850 per night (USD)Expedia
Classic Cape & Bunk House Nearby Downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This house is the perfect home away from home for your Vineyard holiday. The sitting & dining areas with the fully equi ...
From $850 per night (USD)Expedia
From $269 per night (USD)VRBO
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Pet Friendly w/ Fee | BBQ Ready | Outdoor Shower Seeking a relaxing Martha’s Vineyard escape? Look no further than this ...
From $269 per night (USD)VRBO
From $1977 per night (USD)Expedia
Fantastic Waterfront Private Beach & Dock on West Chop
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy everything you love about the Vineyard staying in this updated 4 bedroom house on the outer Vineyard Haven harbor. ...
From $1977 per night (USD)Expedia
From $658 per night (USD)VRBO
Charming 4-bedroom home in marvelous Tisbury walking distance to shops and ferry
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to Lake Street Haven, a beautifully decorated 4 bedroom, 3 bathroom private home located in the heart of Vineyard ...
From $658 per night (USD)VRBO
From $1994 per night (USD)Expedia
Soothing 4-bedroom house with a built full yard andAC in charming Tisbury
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 4-bedroom house in Tisbury is perfect for your escape. With 1 king bed, 2 queen beds, 2 twin bed, and 2 futon, ther ...
From $1994 per night (USD)Expedia
From $1052 per night (USD)VRBO
Spacious 5-bedroom house with AC - near downtown Tisbury
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Serene & Spacious Retreat in Tisbury – Perfect for Your Getaway! Discover the charm and tranquility of this beautiful 5 ...
From $1052 per night (USD)VRBO
From $688 per night (USD)VRBO
Centrally-located 3-bedroom house in Oak Bluffs with Expansive Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Updated Cape in a quiet neighborhood is steps from the State forest and it's miles of bike paths. Ten minutes to Edgarto ...
From $688 per night (USD)VRBO
From $666 per night (USD)VRBO
4-bedroom house in Tisbury for a relaxing getaway - newly renovated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Discover the beauty of Tisbury from this 4-bedroom house. Just a 5 minute walk to a small family beach with gorgeous sun ...
From $666 per night (USD)VRBO
From $2427 per night (USD)VRBO
Luxury Property with Sweeping Views & Private Beach in Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Set back off a bluff with expansive views of Nantucket Sound and beyond to Chappy is this sophisticated waterfront home ...
From $2427 per night (USD)VRBO
From $1303 per night (USD)VRBO
Shady Pines - Pet Friendly Rolling Ranch Near Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Ideally located just one mile from downtown Oak Bluffs, this newly updated home is tucked away on a quiet stree ...
From $1303 per night (USD)VRBO