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

Holiday Homes in Oak Bluffs

  • 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 homes

1. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is NZ$1,318
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown

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, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is NZ$2,344
includes taxes & fees
15 Oct - 16 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

3. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is NZ$1,218
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

4. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
The price is NZ$1,628
includes taxes & fees
15 Oct - 16 Oct
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

5. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
Delightful 3-bedroom house with AC in Oak Bluffs

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is NZ$1,862
includes taxes & fees
27 Oct - 28 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

7. 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, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is NZ$6,533
includes taxes & fees
18 Oct - 19 Oct
Beautiful Estate with salt water pool & pond with kayaks

8. 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)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
The price is NZ$3,711
includes taxes & fees
27 Oct - 28 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

9. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is NZ$1,636
includes taxes & fees
14 Nov - 15 Nov
Walk to Beach! Oak Bluffs Home & Studio

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

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is NZ$2,858
includes taxes & fees
18 Oct - 19 Oct
New 4 BR house near center and beaches with bikes

11. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (45 reviews)
"Great stay!"
United States
Kian S.
The price is NZ$789
includes taxes & fees
18 Oct - 19 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

12. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (224 reviews)
"Great location "
United States
Stephanie B.
The price is NZ$912
includes taxes & fees
1 Nov - 2 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

13. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is NZ$1,923
includes taxes & fees
18 Oct - 19 Oct
The Seashell Cove - Martha's Vineyard

14. 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, (54 reviews)
"We had the best week at 67 Tide Run! The property is gorgeous. We enjoyed kayaking and fishing from the dock. It was plenty big enough for our family of 10. We are going to miss the views. It’s perfect! You cannot go wrong booking Jamie’s home."
United States
cindy w.
The price is NZ$1,970
includes taxes & fees
16 Oct - 17 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

15. Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (101 reviews)
"We had an amazing stay and hope to be back again! The house was clean, comfortable, and just as pictured."
United States
Melina G.
The price is NZ$2,890
includes taxes & fees
18 Oct - 19 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.

16. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is NZ$1,281
includes taxes & fees
15 Oct - 16 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

17. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (45 reviews)
"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."
United States
Kathryn C.
The price is NZ$1,200
includes taxes & fees
20 Oct - 21 Oct
Stunning 4-bedroom Private Fresh Water Beach Front

18. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (4 reviews)
"The home worked out well for our needs. They have a very nice fully fenced in yard which was very beneficial."
United States
Rosemary P.
Recently renovated 3 bedroom

19. Nice home near Mashpee Commons and all Falmouth has to offer

Nice home near Mashpee Commons and all Falmouth has to offer
Falmouth
6.0 out of 10, (3 reviews)
"Quiet location"
United States
andrea m.
Nice home near Mashpee Commons and all Falmouth has to offer

20. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
Haven in Hatchville - newly renovated home
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

Oak Bluffs Holiday Homes information

Number of reviews
517
Accommodation
1334 Holiday Homes
Lowest Price
NZ$789
Highest Price
NZ$6,533