A row of colorful, historic houses with a central path.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Oak Bluffs vacation homes

A circular stone patio with Adirondack chairs and a small table in a forested area.

1. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is ￥50,427
￥114,080 total
includes taxes & fees
Aug 25 - Aug 26
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

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

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is ￥69,417
￥222,992 total
includes taxes & fees
Sep 7 - Sep 8
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

3. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is ￥78,957
￥151,292 total
includes taxes & fees
Sep 16 - Sep 17
Charming Vacation Home in Oak Bluffs.
A spacious living area with a high ceiling, a dining table, and a kitchen area.

4. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is ￥49,842
￥134,326 total
includes taxes & fees
Sep 18 - Sep 19
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

5. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"TLDR: House is nice,"
United States
Rachel
The price is ￥215,433
￥350,441 total
includes taxes & fees
Sep 8 - Sep 9
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

6. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is ￥395,575
￥602,516 total
includes taxes & fees
Sep 16 - Sep 17
Beautiful Estate with salt water pool & pond with kayaks
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

7. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is ￥61,551
￥151,646 total
includes taxes & fees
Aug 31 - Sep 1
Walk to Beach! Oak Bluffs Home & Studio

8. THE HAVEN: No car needed 0.4 m to downtown/beach.

THE HAVEN: No car needed 0.4 m to downtown/beach.
Tisbury
The price is ￥140,031
￥288,855 total
includes taxes & fees
Sep 14 - Sep 15
THE HAVEN: No car needed 0.4 m to downtown/beach.
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

9. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (8 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ￥83,862
￥228,530 total
includes taxes & fees
Sep 7 - Sep 8
New 4 BR house near center and beaches with bikes
A modern kitchen with white cabinets, a wooden dining table, and black chairs.

10. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is ￥84,019
￥164,615 total
includes taxes & fees
Sep 2 - Sep 3
Walk to Town/Golf Club - Renovated Edgartown Home
A two-story house with a brick chimney, a wooden deck, and a wooden fence.

11. serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is ￥55,381
￥131,320 total
includes taxes & fees
Sep 18 - Sep 19
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
A waterfront marina with boats docked, buildings with gabled roofs, and a clear blue sky.

12. Walk to downtown Edgartown in quiet neighborhood - Perfect Location!

Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
Edgartown
10.0 out of 10, Exceptional, (5 reviews)
"One of the most well equipped vacation rentals I’ve stayed in. A simple, but well curated place. Thank you to our hosts!"
United States
Anonymous traveler
The price is ￥119,685
￥200,176 total
includes taxes & fees
Aug 31 - Sep 1
Walk to downtown Edgartown in quiet neighborhood - Perfect Location!
A wooden boardwalk leading to a beach with a lighthouse in the distance.

13. Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (18 reviews)
"This is a beautiful and unique home with plenty of space and activities for the family. The photos were accurate and there was so much space for everyone to relax. We enjoyed our stay so much. "
United States
Lisa F.
The price is ￥57,449
￥127,117 total
includes taxes & fees
Sep 3 - Sep 4
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
A spacious living area with wooden beams, a dining table, and a sofa.

14. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is ￥119,685
￥193,403 total
includes taxes & fees
Sep 6 - Sep 7
The Seashell Cove - Martha's Vineyard
A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

15. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (17 reviews)
"Super neat and clean rental with plenty of space for our large group. We were only there one night but would definitely stay again if in the area!"
United States
Laura K.
The price is ￥63,672
￥150,128 total
includes taxes & fees
Aug 27 - Aug 28
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
A coastal road with a rocky breakwater and a stack of stones.

16. Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (15 reviews)
"We had a family reunion and 75 Locust Street was the central hub of the four night stay. The house is beautiful, clean and we had family from all over stay there. We'd go back in a heartbeat. Easy access to downtown and the hosts were communicative and informative."
United States
Melissa L.
Beautiful Home in Falmouth Village
A beach with clear water and a sandy shore.

17. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (51 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is ￥118,673
￥224,557 total
includes taxes & fees
Aug 29 - Aug 30
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A two-story house with a porch, white chairs, and a red door.

18. The Costal Corner - Martha's Vineyard

The Costal Corner - Martha's Vineyard
Katama
10.0 out of 10, Exceptional, (10 reviews)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
United States
stephen t.
The Costal Corner - Martha's Vineyard
A modern kitchen with white cabinetry, a central island, skylights, and a view of the outdoors.

19. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Stay was awesome! Perfect house for family gatherings "
United States
Diana P.
The price is ￥90,187
￥225,765 total
includes taxes & fees
Aug 23 - Aug 24
Recently renovated 3 bedroom
A spacious kitchen with a large island, wooden ceiling beams, and large windows.

20. Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!

Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
East Falmouth
9.8 out of 10, Exceptional, (76 reviews)
"This property is 100% portrayed as in the photos. The view is exactly as beautiful as in the photos. My family and I enjoyed are stay in this gorgeous home. "
United States
Erin S.
The price is ￥85,375
￥163,828 total
includes taxes & fees
Sep 7 - Sep 8
Beach Front on Beautiful Jenkins Pond, Quiet Area, Discounted off season rates!
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

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"Anything you need is provided in the hotel and around the vicinity. There's a Stop & Shop, cute restaurants, a movie theater, and even a Walmart. The hotel itself is nice, quaint, and cozy- if you want something upscale and lively then elsewhere is recommended. I like to get away from the hustle and bustle when I return to the hotel to rest. So the Admiralty Inn & Suites is just right for me. The outdoor pool is so inviting. Also, the local beaches are minutes away, as well as the ferries to Martha's Vineyard. I'm glad I made this choice and will likely stay at this hotel every time I visit the Cape & Martha's Vineyard. Even if I want to spend a day in Hyannis and Nantucket, I will still choose it."
Dr Jackie 3-night trip
Posted 4 hours ago
Admiralty Inn & Suites - a Red Collection Hotel

Find out more about Oak Bluffs

Oak Bluffs Vacation Homes information

Number of reviews
Accommodation
1396 Vacation Homes
Lowest Price
￥136,700
Highest Price
￥136,700