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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Oak Bluffs holiday rentals

Terrace/patio

Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.6 out of 10, Excellent, (7 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is HK$2,047
HK$4,240 total
includes taxes & fees
17 Aug - 18 Aug
Walk to Beach & Lighthouse: Oak Bluffs Studio!
Smart TV

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, (91 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is HK$3,882
HK$6,158 total
includes taxes & fees
26 Aug - 27 Aug
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Coffee/tea maker, fridge, microwave, oven

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$9,019
HK$15,295 total
includes taxes & fees
7 Aug - 8 Aug
Brand New Guest house
Exterior

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, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is HK$7,513
HK$16,320 total
includes taxes & fees
28 Jul - 29 Jul
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Property grounds

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$3,208
HK$6,535 total
includes taxes & fees
26 Aug - 27 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Sun-loungers, beach towels

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is HK$8,463
HK$13,299 total
includes taxes & fees
30 Jul - 31 Jul
Charming Vacation Home in Oak Bluffs.
Interior

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is HK$10,588
HK$17,512 total
includes taxes & fees
28 Jul - 29 Jul
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Exterior

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$31,370
HK$43,818 total
includes taxes & fees
28 Jul - 29 Jul
Beautiful Estate with salt water pool & pond with kayaks
Interior

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$3,725
HK$5,957 total
includes taxes & fees
26 Aug - 27 Aug
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Terrace/patio

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
Walk to Beach! Oak Bluffs Home & Studio
TV

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is HK$2,353
HK$4,003 total
includes taxes & fees
23 Aug - 24 Aug
Small One Bedroom Private Cottage on Large Quiet Property.
Interior

Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (28 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$1,398
HK$3,339 total
includes taxes & fees
30 Jul - 31 Jul
Brand new! Lovely apartment-Vineyard Haven
Coffee/tea maker, fridge, microwave, oven

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

Walking-distance to town, shops, restaurants & ferry!
Tisbury
10.0 out of 10, Exceptional, (25 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!
Terrace/patio

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (51 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is HK$7,450
HK$11,012 total
includes taxes & fees
31 Jul - 1 Aug
WATERFRONT Downtown Cottage w/ Beach
Private beach nearby, beach bar

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (364 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is HK$3,958
HK$4,530 total
includes taxes & fees
12 Aug - 13 Aug
The Club at New Seabury
Exterior

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, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is HK$6,235
HK$11,432 total
includes taxes & fees
17 Aug - 18 Aug
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
TV

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 place, great location."
United States
James H.
The price is HK$854
HK$2,728 total
includes taxes & fees
17 Aug - 18 Aug
New Seabury Cape Condo + Pool & Beach Escape
Property grounds

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, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is HK$9,403
HK$17,915 total
includes taxes & fees
26 Aug - 27 Aug
New 4 BR house near center and beaches with bikes
Smart TV, DVD player

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (28 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is HK$6,000
HK$9,663 total
includes taxes & fees
29 Jul - 30 Jul
The Seashell Cove - Martha's Vineyard
Beach nearby

Loft Hideaway in Falmouth Village

Loft Hideaway in Falmouth Village
Falmouth
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed our visit!! The location can’t be beat and Falmouth was a great place to explore. "
United States
Nancy F.
The price is HK$1,713
HK$3,486 total
includes taxes & fees
9 Aug - 10 Aug
Loft Hideaway in Falmouth Village
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

Summercamp

Summercamp

10/10 Excellent
"Great as always!"
Claire 2-night trip
Posted 3 hours ago
Summercamp

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?

Quaint, ranch style home in Oak Bluffs with central air: This highly rated holiday home rental in Oak Bluffs is located near the beach, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Oak Bluffs are Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs 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 271 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.