Oak Bluffs Holiday Rentals

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Holiday Rentals in Oak Bluffs

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs
9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
United States
Leon R.
The price is NZ$1,573
includes taxes & fees
26 Nov - 27 Nov
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

Oak Bluffs
9.4 out of 10, Exceptional, (88)
"We loved our stay! It was the perfect location, loved the view, it was sparce but clean. Check in/out was easy and owner was responsive. "
United States
Tracy M.
The price is NZ$871
includes taxes & fees
16 Nov - 17 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is NZ$2,133
includes taxes & fees
21 Nov - 22 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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

Oak Bluffs
9.4 out of 10, Exceptional, (91)
"Location, the water view, delicious restaurants nearby. Apt was comfy, clean. For 1 night only used the fridge. "
United States
Brenda M.
The price is NZ$877
includes taxes & fees
21 Nov - 22 Nov
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (337)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
United States
Rachael
The Club at New Seabury

Steps from Marina, beach, restaurants!

Wareham
9.8 out of 10, Exceptional, (12)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
The price is NZ$415
includes taxes & fees
17 Nov - 18 Nov
Steps from Marina, beach, restaurants!

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

Onset
9.8 out of 10, Exceptional, (28)
"Just as described in listing. Really enjoyed time on deck with water view."
United States
Joan P.
The price is NZ$739
includes taxes & fees
20 Nov - 21 Nov
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable
8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is NZ$914
includes taxes & fees
19 Nov - 20 Nov
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

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

Onset
9.4 out of 10, Exceptional, (9)
"Very spacious, clean, wonderful view, and walking distance from everything. "
United States
Sergio
The price is NZ$739
includes taxes & fees
20 Nov - 21 Nov
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Newly Renovated Martha's Vineyard Vacation Rental!

Katama
9.6 out of 10, Exceptional, (47)
"Very nice house that served our needs. Well located. Nicely appointed. The bedroom downstairs with twin beds accommodated my elderly mother who has trouble with stairs. No real maintenance issues other than, the gfci outlets in the bathrooms did not work."
United States
Silvia B.
The price is NZ$1,048
includes taxes & fees
21 Nov - 22 Nov
Newly Renovated Martha's Vineyard Vacation Rental!

Amazing Onset Getaway in the Starfish Suite

Onset
9.8 out of 10, Exceptional, (23)
"The place was very nice and it was right next to the beach. We had everything we needed and it had a cute outdoor space. "
United States
Yen-Yen P.
The price is NZ$809
includes taxes & fees
16 Nov - 17 Nov
Amazing Onset Getaway in the Starfish Suite

Spacious and Bright , Very Close to Beach!

Onset
9.6 out of 10, Exceptional, (22)
"wonderful location - clean and well maintained."
United States
lisa j.
The price is NZ$744
includes taxes & fees
16 Nov - 17 Nov
Spacious and Bright , Very Close to Beach!

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Barnstable
10.0 out of 10, Exceptional, (4)
"Great property for families- loved the downstairs pool table and outside area with fire pit and volleyball net. Super clean. Highly recommend. "
United States
Erica C.
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Charming studio in tranquil Falmouth with AC

Falmouth
The price is NZ$365
includes taxes & fees
28 Nov - 29 Nov
Charming studio in tranquil Falmouth with AC

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

Falmouth
10.0 out of 10, Exceptional, (207)
"The house was even nicer than the pictures. We came in March for a long weekend with some friends and had a really great time. Walking distance to so many fun things- great house for all ages!"
United States
Briget R.
The price is NZ$874
includes taxes & fees
24 Nov - 25 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth
10.0 out of 10, Exceptional, (11)
"We LOVED our stay. The home is gorgeous and comfortable with everything we needed. The kids loved the game barn. Nicely located. We loved the deck. Would stay again!"
United States
Enid G.
The price is NZ$1,276
includes taxes & fees
16 Nov - 17 Nov
Spring Escape in Hatchville – Sleeps 6 + Dogs!

3-bedroom house in charming Barnstable with WiFi, AC,Walking distance to Main st

Barnstable
10.0 out of 10, Exceptional, (1)
"Excellent property with a great location"
United States
David B.
The price is NZ$729
includes taxes & fees
27 Nov - 28 Nov
3-bedroom house in charming Barnstable with WiFi, AC,Walking distance to Main st

Sal's Place

2.0 star property
Hyannis
The price is NZ$775
includes taxes & fees
20 Nov - 21 Nov
Sal's Place

The Seashell Cove - Martha's Vineyard

Katama
9.8 out of 10, Exceptional, (23)
"My family and I had a great stay in this lovely home!! The house had everything we needed and was a great starting point for all island adventures. Charles was so helpful throughout the entire trip. We would most certainly stay here again!"
United States
Caryn I.
The price is NZ$1,010
includes taxes & fees
15 Dec - 16 Dec
The Seashell Cove - Martha's Vineyard

Hyannis Hideaway in Cape Cod

Barnstable
10.0 out of 10, Exceptional, (2)
"We had a great time at Hyannis Hideaway! The location was PERFECT! We were no more than 6 minutes to the beach. 2 minutes from stores and restaurants! AC units in every room to keep us cool. The house was so clean and spacious for our big group. We can’t wait to go back!"
United States
Ashleigh I.
The price is NZ$1,095
includes taxes & fees
16 Nov - 17 Nov
Hyannis Hideaway in Cape Cod
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 favorite 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 depends 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 NZ$871 per night. Entering your travel dates in the search wizard you might find 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?

MOST CHIC SPOT! Your Martha's Vineyard Getaway!: This highly rated holiday home rental in Oak Bluffs is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 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 Updated house close to town and beach with patio, AC, and games 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 260 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 lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Oak Bluffs Fishing Pier. Other places in town to visit include Circuit Avenue and Flying Horses Carousel.

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.