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

Oak Bluffs Vacation Rentals

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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 rentals

Smart TV

1. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (92 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is ￥47,796
￥85,421 total
includes taxes & fees
Sep 10 - Sep 11
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Property grounds

2. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is ￥39,830
￥81,328 total
includes taxes & fees
Sep 2 - Sep 3
Make Lasting Memories In This Adorable Vineyard Cottage!
Property grounds

3. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is ￥31,705
￥119,768 total
includes taxes & fees
Sep 7 - Sep 8
Lovely two bedroom apartment with indoor fireplace
Property grounds

4. 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 ￥50,345
￥113,895 total
includes taxes & fees
Aug 31 - Sep 1
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Exterior

5. 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 ￥69,304
￥222,629 total
includes taxes & fees
Sep 7 - Sep 8
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Coffee/tea maker, fridge, microwave, oven

6. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is ￥65,321
￥162,299 total
includes taxes & fees
Sep 7 - Sep 8
Brand New Guest house
Sun loungers, beach towels

7. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is ￥79,501
￥152,334 total
includes taxes & fees
Sep 8 - Sep 9
Charming Vacation Home in Oak Bluffs.
TV, fireplace, books

8. 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 ￥50,186
￥133,827 total
includes taxes & fees
Sep 11 - Sep 12
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Interior

9. 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 ￥215,082
￥345,243 total
includes taxes & fees
Sep 8 - Sep 9
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Exterior

10. 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 ￥390,334
￥596,523 total
includes taxes & fees
Sep 16 - Sep 17
Beautiful Estate with salt water pool & pond with kayaks
Interior

11. Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs
9.4 out of 10, Exceptional, (96 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is ￥67,711
￥110,871 total
includes taxes & fees
Sep 9 - Sep 10
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Terrace/patio

12. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is ￥61,975
￥152,690 total
includes taxes & fees
Aug 31 - Sep 1
Walk to Beach! Oak Bluffs Home & Studio
Interior

13. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is ￥31,832
￥72,216 total
includes taxes & fees
Aug 27 - Aug 28
Brand new! Lovely apartment-Vineyard Haven
Private beach nearby, beach bar

14. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (366 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is ￥40,263
￥46,081 total
includes taxes & fees
Sep 7 - Sep 8
The Club at New Seabury
Interior

15. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Terrace/patio

16. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (53 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is ￥143,388
￥210,884 total
includes taxes & fees
Aug 20 - Aug 21
WATERFRONT Downtown Cottage w/ Beach
Smart TV, fireplace, books, printers

17. Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (39 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is ￥135,263
￥172,265 total
includes taxes & fees
Sep 6 - Sep 7
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Coffee/tea maker, fridge, microwave, oven

18. Walking-distance to town, shops, restaurants & ferry!

Walking-distance to town, shops, restaurants & ferry!
Tisbury
10.0 out of 10, Exceptional, (26 reviews)
"I rented this for my staff, and they said it was the best place they have stayed on Martha's Vineyard."
United States
else r.
Walking-distance to town, shops, restaurants & ferry!
TV

19. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (85 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is ￥17,350
￥56,141 total
includes taxes & fees
Sep 2 - Sep 3
New Seabury Cape Condo + Pool & Beach Escape
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

8/10 Good
"I did not like the tight parking to fit two vehicles in each section underneath the support legs of the parking lot solar array. People did not even think of leaving enough space for a second vehicle in each section. They should have been told to make room for a second vehilce."
Daniel 1-night trip
Posted 1 hour ago
Admiralty Inn & Suites - a Red Collection Hotel

Find out more about Oak Bluffs

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Frequently asked questions

Can I find vacation rentals in Oak Bluffs?

Yes, you can find vacation rentals in Oak Bluffs near Flying Horses Carousel, or you can go with a more secluded option if you're looking for extra privacy while you relax. The shops and waterfront are just a few reasons why tourists like Oak Bluffs. Allow lots of time to check out the beaches and wineries during your visit.

What are some of the best vacation rentals in Oak Bluffs?

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.: Visitors give good reviews to this Oak Bluffs vacation home rental, which offers a fireplace, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Oak Bluffs are Quaint, ranch style home in Oak Bluffs with central air and Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs.

How many vacation rentals will I find in Oak Bluffs?

Choose from 278 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

What can I see and do in Oak Bluffs?

Ocean Park and Oak Bluffs Town Beach are a couple of scenic spots to enjoy the outdoors, whereas Cottage Museum is one of the cultural attractions. Other places in town to visit include Circuit Avenue and Oak Bluffs Harbor.

What are vacation rentals like in Oak Bluffs?

Vacation rentals are private accommodations you can reserve for several days or longer in Oak Bluffs. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.