Oak Bluffs Vacation Rentals from CA $344: 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 265 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

Q: What can I see and do in Oak Bluffs?

Oak Bluffs Town Beach and Inkwell 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.

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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In two weeks

In two months

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Our top choices for Oak Bluffs vacation rentals

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

Oak Bluffs

Cassandra

CA $747 total

includes taxes & fees

Oct 4 - Oct 5

2. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Oak Bluffs

Linda T.

CA $1,241 total

includes taxes & fees

Sep 28 - Sep 29

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

Oak Bluffs

Diana

CA $867 total

includes taxes & fees

Sep 23 - Sep 24

On the beach, sun loungers, beach towels

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

Oak Bluffs

Rachael C.

CA $1,291 total

includes taxes & fees

Sep 24 - Sep 25

5. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs

Sherri R.

CA $1,905 total

includes taxes & fees

Oct 1 - Oct 2

6. < 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 $1,294 total

includes taxes & fees

Sep 23 - Sep 24

Coffee/tea maker, fridge, microwave, oven

7. Brand New Guest house

Oak Bluffs

Elizabeth O.

CA $1,339 total

includes taxes & fees

Oct 1 - Oct 2

8. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

Oak Bluffs

Bethann N.

CA $937 total

includes taxes & fees

Sep 29 - Sep 30

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Top Oak Bluffs Hotel Reviews

Falmouth Inn

8/10 Good

"Breakfast toaster needs to work better or replaced everything else was good."

Faraway Martha's Vineyard

8/10 Good

"A few smaller items that made the stay slightly questionable, no elevator bags had to be carried. Not much to do about that in an historical building, but it's a note for guests. I would expect a notch better, especially when coming to bedding. The bed was comfortable, but I would expect down pillows and blanket at this price point. The record player was a lovely touch. Parking was challenging, but again, historical town we must make compromises. Wonderful shower towels, GREAT pool and hot tub area. The location of the hotel is / was supreme. Only coffee offered in the lobby, no inroom machine, and no option of a latte, or capp in the hotel or lobby, only in adjacent restaurant. (Loud bathroom fan, bug in room, a little mildew build up on the shower grout, definite degradation happening on plumbing fixtures. At this price point, should be better)"

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

8/10 Good

"The property was as described, tranquil. It's within walking distance to Oak Bluffs downtown at 1.4 miles. It was built in 1966 and looks like a place from that period with wood paneling, older low toilets etc. Our only minor issue was a toilet that kept running intermittently. Altogether we were very satisfied."

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 $344 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 265 Expedia vacation rentals in Oak Bluffs for a memorable vacation.

What can I see and do in Oak Bluffs?

Oak Bluffs Town Beach and Inkwell 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.

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Check prices for these dates

Our top choices for Oak Bluffs vacation rentals

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

2. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

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

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

5. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

6. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

7. Brand New Guest house

8. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

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

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

11. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

12. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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

14. Walk to Beach! Oak Bluffs Home & Studio

15. Brand new! Lovely apartment-Vineyard Haven

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

17. The Club at New Seabury

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

19. Charming 3 Bedroom Apartment . Walk to Ferry, Shops & Beach

20. New Seabury Cape Condo + Pool & Beach Escape

Find vacation rentals that suit your style

Top Oak Bluffs Hotel Reviews

Falmouth Inn

Inn on the Square

MV Surfside Hotel

AutoCamp Cape Cod

Pequot Hotel

The Attleboro House

Faraway Martha's Vineyard

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Quaint, ranch style home in Oak Bluffs with central air

Find out more about Oak Bluffs

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