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Browse Select Oak Bluffs Holiday Homes

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.2 out of 10, (24)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

8.4 out of 10, Very good, (39)
"Close to the beach , clean and a wonderful Vineyard stay"
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard

Waterfront Home w/ Guest Cottage

10.0 out of 10, Exceptional, (1)
"I lined the view from the home and the safety in the area! Overall, great place for a big family !"
Waterfront Home w/ Guest Cottage

Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

7.4 out of 10, Good, (3)
"We had a wonderful early-June weekend stay at this charming house minutes walk from town. Highlights were reading on the rocking chair on the deck and playing games in the screened-in porch. Everything looks just like in the listing - charming, warm, like staying at your grandpa's beach house. There were a few bumps - the listed dryer was in a locked shed, a faucet wasn't working - but our sense was this is a new listing and details are still being ironed out. None of that interfered with our...
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer

Best Kept Secret Retreat for Adults with Water & Golf Course Views!

10.0 out of 10, Exceptional, (37)
"The home was beautiful and very well appointed. Easily accommodated our group of 8 adults with room to spare. Minor complaint is that there could’ve been a few more towels available, but the washer and dryer took care of that."
Best Kept Secret Retreat for Adults with Water & Golf Course Views!

Spacious colonial home close to town with AC, porches, & W/D

10.0 out of 10, Exceptional, (5)
Spacious colonial home close to town with AC, porches, & W/D

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

The price is £474
includes taxes & fees
11 Sept - 12 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Updated house close to town and beach with patio, AC, and games

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great location, walking distance to beach, restaurants and shops!"
Updated house close to town and beach with patio, AC, and games

Quaint, ranch style home in Oak Bluffs with central air

2.0 star property
10.0 out of 10, Exceptional, (1)
"Exactly as expected. Very clean and was nice and cool upon arrival. Well stocked and had everything we needed for our stay, including towels, linens, toiletries, and cleaning supplies. Very quick responses from property management. Phenomenal location. Perfect for anyone looking for a solid, clean and comfortable camp on the island. "
Quaint, ranch style home in Oak Bluffs with central air

Cozy getaway in a central location w/ a full kitchen & furnished deck

6.8 out of 10, (23)
"The furniture and amenities provided were good"
Cozy getaway in a central location w/ a full kitchen & furnished deck

Private house with jetted tub, deck, grill, central AC and large yard

6.0 out of 10, (1)
"We love the layout. It was beautiful modern and open. The large rooms and high ceilings felt luxurious. The location was convenient, although not within walking distance to the beach a lovely space for a retreat in Martha’s Vineyard."
Private house with jetted tub, deck, grill, central AC and large yard

Quaint,,,Quiet..up island feel yet a short walk to town and harbor

9.8 out of 10, Exceptional, (92)
"Awesome, fun place. Has everything you need for a great Vineyard stay!"
Quaint,,,Quiet..up island feel yet a short walk to town and harbor

Spacious island home near Farm Neck Golf Course, the beach and town

10.0 out of 10, Exceptional, (1)
"Great house, great location - perfect space for our large group."
Spacious island home near Farm Neck Golf Course, the beach and town

Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w/AC

10.0 out of 10, Exceptional, (30)
"The location is nice and secluded, yet within walking distance to town and the beach. "
Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w/AC

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
The price is £1,805
includes taxes & fees
3 Sept - 4 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Historic Home with Gorgeous Antiques & Mondern Conveniences

6.8 out of 10, (22)
"Walking distance to beach, ferry, and town"
Historic Home with Gorgeous Antiques & Mondern Conveniences

"The Carousel House" - Ocean Park - Featured in New York Times

9.8 out of 10, Exceptional, (55)
"We had a great stay. Communication was clear and the house was clean. We loved the convenience where everything is a walkable distance. "
"The Carousel House" - Ocean Park - Featured in New York Times

CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

9.6 out of 10, Exceptional, (30)
"This home was absolutely beautiful. In a great location to get anywhere in the island. The host was extremely helpful when needed. I would one hundred percent recommend this place to anybody! "
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

9.4 out of 10, Exceptional, (3)
"The home was clean and comfortable. Our host was very friendly and responsive. Overall a great experience!"
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice nostalgic home Needs minor work (Toilet seats)(Middle room mirror )AC "
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Oak Bluffs Hotel Reviews