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

Oak Bluffs Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Oak Bluffs holiday rentals

Property grounds

1. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (153 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is HK$1,961
HK$4,005 total
includes taxes & fees
2 Sept - 3 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!
Smart TV

2. 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 HK$3,334
HK$5,459 total
includes taxes & fees
1 Sept - 2 Sept
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Exterior

3. Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Oak Bluffs
10.0 out of 10, Exceptional, (47 reviews)
"Great accommodations and a perfect location for the beach, shopping and great food."
United States
Hugh M.
The price is HK$3,099
HK$5,705 total
includes taxes & fees
26 Aug - 27 Aug
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
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 HK$1,687
HK$4,600 total
includes taxes & fees
8 Sept - 9 Sept
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, (7 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is HK$3,413
HK$11,094 total
includes taxes & fees
6 Sept - 7 Sept
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, (5 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 HK$3,883
HK$8,859 total
includes taxes & fees
24 Aug - 25 Aug
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 HK$3,915
HK$7,501 total
includes taxes & fees
8 Sept - 9 Sept
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 HK$2,471
HK$6,660 total
includes taxes & fees
8 Sept - 9 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Exterior

9. 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 HK$23,535
HK$33,614 total
includes taxes & fees
7 Sept - 8 Sept
Beautiful Estate with salt water pool & pond with kayaks
Interior

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

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (11 reviews)
"TLDR: House is nice,"
United States
Rachel
The price is HK$10,591
HK$17,263 total
includes taxes & fees
8 Sept - 9 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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, (94 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is HK$3,334
HK$5,459 total
includes taxes & fees
8 Sept - 9 Sept
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 HK$3,052
HK$7,518 total
includes taxes & fees
1 Sept - 2 Sept
Walk to Beach! Oak Bluffs Home & Studio
TV

13. 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 HK$854
HK$2,720 total
includes taxes & fees
2 Sept - 3 Sept
New Seabury Cape Condo + Pool & Beach Escape
Interior

14. 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 HK$3,428
HK$5,932 total
includes taxes & fees
27 Aug - 28 Aug
Brand new! Lovely apartment-Vineyard Haven
Terrace/patio

15. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (52 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is HK$7,766
HK$11,409 total
includes taxes & fees
8 Sept - 9 Sept
WATERFRONT Downtown Cottage w/ Beach
Coffee/tea maker, fridge, microwave, oven

16. 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!
Exterior

17. NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (18 reviews)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
The price is HK$6,237
HK$11,462 total
includes taxes & fees
17 Aug - 18 Aug
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Interior

18. 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.
The price is HK$2,353
HK$4,206 total
includes taxes & fees
2 Sept - 3 Sept
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
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

Falmouth Inn

Falmouth Inn

10/10 Excellent
"Super clean."
Robert 1-night trip
Posted 2 hours ago
Falmouth Inn

Find out more about Oak Bluffs

Search for holiday rentals in Oak Bluffs on Expedia! You can easily find your home rentals, villas, holiday apartments in Oak Bluffs using one of the methods below:

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Look no further and take a look at our great range of rental properties in Oak Bluffs!

Frequently asked questions

Can I find holiday rentals in Oak Bluffs?

Yes, there are holiday rentals in Oak Bluffs close to Flying Horses Carousel, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Oak Bluffs has to offer?

Victorian cottage overlooking downtown Oak Bluffs and the Harbor.: This highly rated holiday home rental in Oak Bluffs 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 that you can cook with friends or family. Other favourite homes for rent in Oak Bluffs are Quaint, ranch style home in Oak Bluffs with central air and Bright old-world cottage with two porches & large yard - walk to town & beaches.

How many holiday rentals will I find in Oak Bluffs?

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

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 holiday rentals like in Oak Bluffs?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oak Bluffs. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.