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

Oak Bluffs Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oak Bluffs holiday rentals

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 NZ$870
includes taxes & fees
10 Sept - 11 Sept
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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, (154 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is NZ$828
includes taxes & fees
2 Sept - 3 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!

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 NZ$1,243
includes taxes & fees
7 Sept - 8 Sept
Lovely two bedroom apartment with indoor fireplace

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 NZ$1,200
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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 NZ$2,332
includes taxes & fees
6 Sept - 7 Sept
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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 NZ$1,685
includes taxes & fees
7 Sept - 8 Sept
Brand New Guest house

7. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is NZ$1,581
includes taxes & fees
8 Sept - 9 Sept
Charming Vacation Home in Oak Bluffs.

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 NZ$1,405
includes taxes & fees
11 Sept - 12 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 NZ$3,681
includes taxes & fees
8 Sept - 9 Sept
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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 NZ$6,310
includes taxes & fees
13 Sept - 14 Sept
Beautiful Estate with salt water pool & pond with kayaks

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, (95 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is NZ$1,134
includes taxes & fees
8 Sept - 9 Sept
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

12. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is NZ$1,571
includes taxes & fees
31 Aug - 1 Sept
Walk to Beach! Oak Bluffs Home & Studio

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 NZ$752
includes taxes & fees
27 Aug - 28 Aug
Brand new! Lovely apartment-Vineyard Haven

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 NZ$491
includes taxes & fees
7 Sept - 8 Sept
The Club at New Seabury

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.
The price is NZ$1,026
includes taxes & fees
1 Sept - 2 Sept
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and 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 NZ$2,172
includes taxes & fees
20 Aug - 21 Aug
WATERFRONT Downtown Cottage w/ Beach

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 NZ$1,827
includes taxes & fees
6 Sept - 7 Sept
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

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!

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 NZ$579
includes taxes & fees
2 Sept - 3 Sept
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oak Bluffs Hotel Reviews

Find out more about Oak Bluffs

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oak Bluffs holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oak Bluffs. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oak Bluffs. Seeing all the best attractions is bound to make you fall in love with Oak Bluffs. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oak Bluffs short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

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

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.