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

Oak Bluffs Holiday Rentals

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Our top choices for Oak Bluffs holiday rentals

Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very good, (6 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is AU$487
includes taxes & fees
23 July - 24 July
Walk to Beach & Lighthouse: Oak Bluffs Studio!

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, (93 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is AU$1,000
includes taxes & fees
22 July - 23 July
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (4 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 AU$2,684
includes taxes & fees
7 Aug - 8 Aug
Brand New Guest house

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)
"I was able to get to the house within minutes from the Vineyard Haven ferry. There was plenty of parking. The house was immaculate and well appointed. The beaches and restaurants nearby were great. It was also very convenient to find on the way back from a long day. The beds are very comfortable."
United States
Ross
The price is AU$1,007
includes taxes & fees
24 July - 25 July
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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 AU$2,892
includes taxes & fees
26 July - 27 July
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (6 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is AU$3,389
includes taxes & fees
1 Aug - 2 Aug
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 AU$3,102
includes taxes & fees
26 July - 27 July
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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 AU$5,670
includes taxes & fees
22 July - 23 July
Beautiful Estate with salt water pool & pond with kayaks

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 AU$1,000
includes taxes & fees
22 July - 23 July
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is AU$2,182
includes taxes & fees
3 Aug - 4 Aug
Walk to Beach! Oak Bluffs Home & Studio

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.
Small One Bedroom Private Cottage on Large Quiet Property.

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.
Brand new! Lovely apartment-Vineyard Haven

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (50 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is AU$2,288
includes taxes & fees
20 Aug - 21 Aug
WATERFRONT Downtown Cottage w/ Beach

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.
The price is AU$1,696
includes taxes & fees
3 Aug - 4 Aug
Walking-distance to town, shops, restaurants & ferry!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (60 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is AU$1,615
includes taxes & fees
16 Aug - 17 Aug
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (84 reviews)
"Great place, great location."
United States
James H.
The price is AU$497
includes taxes & fees
17 Aug - 18 Aug
New Seabury Cape Condo + Pool & Beach Escape

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place! Clean! Great communication! Clean and well stocked. A pleasure to deal with."
United States
Kelly H.
4-bedroom house in lovely Edgartown..Centrally located

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 AU$2,015
includes taxes & fees
17 Aug - 18 Aug
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (363 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 AU$826
includes taxes & fees
11 Aug - 12 Aug
The Club at New Seabury

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is AU$383
includes taxes & fees
27 July - 28 July
Charming studio in tranquil Falmouth with AC
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

Find out more about Oak Bluffs

Everything you need to know about Oak Bluffs holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Bluffs holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oak Bluffs holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Bluffs. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Bluffs holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs holiday rentals we have selected for you start as low as AU$826 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Bluffs rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Bluffs holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Bluffs. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This highly rated holiday home rental in Oak Bluffs is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. 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 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.