Oak Bluffs Vacation Rentals from $642: Search Short-Term Rentals

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Our top choices for Oak Bluffs vacation rentals

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs

Louis R.

$1,886 nightly

Jul 5 - Jul 6

Total with taxes and fees

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Oak Bluffs

Stephen S.

$680 nightly

Jun 30 - Jul 1

Total with taxes and fees

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs

Swathanthra M.

$1,946 nightly

Jul 9 - Jul 10

Total with taxes and fees

Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

"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...

Miriam D.

$2,840 nightly

Jun 28 - Jun 29

Total with taxes and fees

On the beach, sun loungers, beach towels

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Oak Bluffs

Stephanie

$1,054 nightly

Jul 10 - Jul 11

Total with taxes and fees

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Oak Bluffs

Ashley S.

$626 nightly

Jun 29 - Jun 30

Total with taxes and fees

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Hyannis

$318 nightly

Jun 28 - Jun 29

Total with taxes and fees

The Sky-High Beach House: Panoramic Waterfront views

Fairhaven

$466 nightly

Jul 14 - Jul 15

Total with taxes and fees

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Top Oak Bluffs Hotel Reviews

AutoCamp Cape Cod

10/10 Excellent

"It was all great, especially for a first-timer."

Summercamp

10/10 Excellent

"Location was perfect in Oak Bluffs close to the ferry terminal and nearby attractions. The staff was very attentive and friendly and the little things at the hotel helped to make the stay enjoyable like the popcorn, coffee/tea, outdoor seating and common areas. Really enjoyed our stay with the family at Summercamp and would highly recommend. The only thing I wish was different was that the recreation room was utilized for 2 out of the 3 days we were there. If we were told that upon check-in it would have helped set the expectation with our kids, as opposed to the kids seeing what was available in the rec room on day 1 and then constantly asking if they could go only to find out that it was closed to a private event."

Sea Crest Beach Resort

8/10 Good

"We had an okay stay overall. The rooms were clean, and the restaurant was excellent. Unfortunately, one day during our visit the property lost power from 9:00 a.m. until 1:00 p.m., which was inconvenient. We stayed after Memorial Day and were disappointed to find that some of the advertised amenities, including the pizza and ice cream shops, were closed. Additionally, the indoor pool was not very enjoyable, as the water temperature was around 85 degrees and felt too warm to be refreshing. While there were some positives, the unavailable amenities and power outage impacted our overall experience."

Harbor View Hotel

10/10 Excellent

"Property was Beautiful. Only downside was there is no Elevator in the area we stayed which was a pain being on 3rd floor with a baby/carrage etc. My fault for not checking ahead of time but other than that the place was great. Close walking distance to downtown Edgartown. Staff was very friendly and accomodating."

Find out more about Oak Bluffs

Everything you need to know about Oak Bluffs vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Bluffs vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oak Bluffs vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oak Bluffs in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $642 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oak Bluffs rentals

At Expedia, we put the best Oak Bluffs vacation 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 vacation.

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.

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Frequently asked questions

Can I find vacation rentals in Oak Bluffs?

Yes, you can find vacation rentals in Oak Bluffs near Flying Horses Carousel, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Oak Bluffs?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: Visitors give good reviews to this Oak Bluffs vacation home rental, which is located in the city center and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Other favorite 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 vacation rentals will I find in Oak Bluffs?

Choose from 270 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

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 vacation rentals like in Oak Bluffs?

Vacation rentals are private accommodations you can reserve for several days or longer in Oak Bluffs. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.

Oak Bluffs Vacation Rentals

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Check prices for these dates

Our top choices for Oak Bluffs vacation rentals

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Beautiful Estate with salt water pool & pond with kayaks

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

The Sky-High Beach House: Panoramic Waterfront views

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

5 Mi to Beach: Cape Cod Getaway w/ Grill

New Seabury Cape Condo + Pool & Beach Escape

Spacious and Bright , Very Close to Beach!

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Luxury Monument Beach Villa /Short term rentals

Charming studio in tranquil Falmouth with AC

Serene Haven w/ No Shared Spaces | Cape Cod

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

4-bedroom house in lovely Edgartown..Centrally located

Find vacation rentals that suit your style

Top Oak Bluffs Hotel Reviews

AutoCamp Cape Cod

Find out more about Oak Bluffs

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