Oak Bluffs Vacation Rentals from CA $205: Short-Term Rentals for 2026

Q: 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.

Q: What are some of the best vacation rentals in Oak Bluffs?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel : Visitors give good reviews to this Oak Bluffs vacation home rental, which is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Other favorite homes for rent in Oak Bluffs are Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs and Quaint, ranch style home in Oak Bluffs with central air .

Q: How many vacation rentals will I find in Oak Bluffs?

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

Q: 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 Flying Horses Carousel.

Q: 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.

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Our top choices for Oak Bluffs vacation rentals

An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

1. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Oak Bluffs

Donna R.

CA $549 total

includes taxes & fees

Nov 22 - Nov 23

A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

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

Oak Bluffs

Sherise M.

CA $678 total

includes taxes & fees

Nov 7 - Nov 8

3. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Oak Bluffs

CA $392 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

4. Vineyard Luxury "Yurt"

Oak Bluffs

David C.

CA $612 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with stainless steel appliances, a dining area with a wooden table set for six, and a living area with a sofa and TV.

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

Oak Bluffs

Chris S.

CA $942 total

includes taxes & fees

Nov 13 - Nov 14

A circular stone patio with Adirondack chairs and a small table in a forested area.

6. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Eli R.

CA $860 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

7. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

Oak Bluffs

"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...

Kate K.

CA $1,247 total

includes taxes & fees

Nov 9 - Nov 10

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

Oak Bluffs

Cassandra

CA $680 total

includes taxes & fees

Nov 8 - Nov 9

A two-story house with a stone facade, a covered patio, and a well-maintained garden.

9. Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

Lamar A.

CA $4,352 total

includes taxes & fees

Nov 30 - Dec 1

10. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

CA $1,172 total

includes taxes & fees

Nov 9 - Nov 10

A row of white lounge chairs with blue cushions, arranged under a white canopy, overlooking the sea.

11. The Club at New Seabury

New Seabury

Kathleen

CA $236 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with wicker chairs and a round table with a sun design.

12. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Tisbury

Adrienne W.

A patio with wicker chairs and a small table, a grassy yard, a wooden fence, and a view of a body of water.

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

Seconsett Island

Michele M.

CA $613 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

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

Katama

Susan M.

CA $2,329 total

includes taxes & fees

Nov 16 - Nov 17

15. Charming Guesthouse | Walk to Beach | Downtown

Falmouth

"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...

Kandy W.

CA $796 total

includes taxes & fees

Nov 7 - Nov 8

A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

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

Falmouth

Stephanie B.

CA $731 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

17. Charming studio in tranquil Falmouth with AC

Falmouth

Harry H.

CA $321 total

includes taxes & fees

Nov 9 - Nov 10

A covered outdoor seating area with a view of the ocean, a ceiling fan, and a flat-screen TV on the wall.

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

East Falmouth

Ben L.

CA $1,359 total

includes taxes & fees

Nov 19 - Nov 20

A spacious living area with wooden beams, a dining table, and a sofa.

19. The Seashell Cove - Martha's Vineyard

Katama

Eric C.

CA $1,483 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with a large window overlooking a lake, a dining area with chairs, and a living room with a sofa.

20. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Sandwich

Sean H.

CA $541 total

includes taxes & fees

Nov 7 - Nov 8

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Find vacation rentals that suit your style

Top Oak Bluffs Hotel Reviews

A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

Madison Inn

Oak Bluffs

10/10 Excellent

Anonymous traveller

A spacious living room with a sofa, chairs, a coffee table, and a staircase.

Morgan Hotel

Oak Bluffs

10/10 Excellent

Fred Di

A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

Faraway Martha's Vineyard

Edgartown

10/10 Excellent

Alicia

A large, multi-story house with a covered porch and a well-maintained lawn.

Shore Haven Inn

Falmouth

10/10 Excellent

Jamie

A two-story house with a brick pathway leading to the front door, surrounded by a well-maintained lawn and green Adirondack chairs.

The Franklin Hotel Martha's Vineyard

Edgartown

10/10 Excellent

Martha

A bedroom with a bed, bedside tables, a chair, a table, and a view of the outdoors.

The Coonamessett

Falmouth

10/10 Excellent

We stayed for 2 nights in early Aug 2015. When we checked in we were told we had an upgrade due to a large group staying at the hotel. We ended up with a huge suite! It was very quiet, peaceful and relaxing. There is a great restaurant and bar right in the inn and also a fun pub next door that features live music, lots of fun! The bed and linens were excellent and the room size was very large. A bit of a "grand old dame", but well-maintained and very clean. Staff helped with taking the...

HJTours Inc

A cozy room with wicker furniture, a stone fireplace, and a view of the ocean.

Inn on the Sound

Falmouth Heights

10/10 Excellent

My wife and I were celebrating our anniversary and decided to head to Cape Cod. With so many options of where to stay we began to read reviews and settled on the Inn on the Sound. I cannot be happier. The facilities were great, the room spacious and tastefully decorated and the food (breakfast) was outstanding. The location made walking to the beach or to dinner, only a few steps away. I would highly recommend staying here. Jon, Debbie and team should be congratulated on running a first rate...

Peter

A modern building with a sign reading "WALMOUTH TIDES" near the beach.

Falmouth Tides

Falmouth Heights

10/10 Excellent

Jay

A spacious living area with a dining table, sofas, and a view of the sea.

Harbor View Hotel

Edgartown

10/10 Excellent

suzanne

A multi-story hotel with a grand entrance, a flagpole, and a well-lit facade.

Vineyard Square Hotel & Suites

Edgartown

10/10 Excellent

Scott

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Bluffs vacation rentals we have selected for you start as low as CA $205 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 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.

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?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: Visitors give good reviews to this Oak Bluffs vacation home rental, which is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Other favorite homes for rent in Oak Bluffs are Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs and Quaint, ranch style home in Oak Bluffs with central air.

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 Flying Horses Carousel.

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

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oak Bluffs vacation rentals

1. Walk to Beach & Lighthouse: Oak Bluffs Studio!

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

3. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

4. Vineyard Luxury "Yurt"

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

6. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

7. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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

9. Beautiful Estate with salt water pool & pond with kayaks

10. Walk to Beach! Oak Bluffs Home & Studio

11. The Club at New Seabury

12. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

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

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

15. Charming Guesthouse | Walk to Beach | Downtown

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

17. Charming studio in tranquil Falmouth with AC

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

19. The Seashell Cove - Martha's Vineyard

20. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Find vacation rentals that suit your style

Top Oak Bluffs Hotel Reviews

Madison Inn

10/10 Excellent

Find out more about Oak Bluffs

Oak Bluffs vacation rentals: An excellent choice for every season

How to find incredible deals on Oak Bluffs rentals

Frequently Asked Questions

Can I find vacation rentals in Oak Bluffs?

What are some of the best vacation rentals in Oak Bluffs?

How many vacation rentals will I find in Oak Bluffs?

What can I see and do in Oak Bluffs?

What are vacation rentals like in Oak Bluffs?