The Best Oak Bluffs, MA Resorts from $103

Q: What is Oak Bluffs like for a resort vacation?

You deserve to get away, and a resort is just the place to indulge in all the amenities and services you need for a relaxing stay in Oak Bluffs. One of the comfortable resorts in the surrounding area could be just what you're looking for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or fun activities to try.

Q: What's a favorite resort in Oak Bluffs?

Here's our top-rated Oak Bluffs resort: The Island Inn on Martha's Vineyard - Golf resort. Features a seasonal outdoor pool, 3 outdoor tennis courts, and a beach shuttle.

Q: What can I do in Oak Bluffs?

Travelers enjoy exploring the beaches, and have good things to say about the shopping and other activities. Monuments like Trinity Park Tabernacle and East Chop Light are places to learn more about the local history, or you can head to Oak Bluffs Town Beach and Inkwell Beach for some time by the water. Additional attractions in the area include Circuit Avenue and Flying Horses Carousel.

Q: What's the weather like in Oak Bluffs?

The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Oak Bluffs is 47 inches.

Q: What's the best way to get to and around Oak Bluffs?

Fly into Vineyard Haven, MA (MVY-Martha's Vineyard), which is located 5.2 mi (8.3 km) from the heart of the city. Otherwise, you can search for flights to Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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Recommended hotels in Oak Bluffs

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

1. Madison Inn

Oak Bluffs

Melissa

$207 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

2. Morgan Hotel

Oak Bluffs

Anika

$136 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

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

Oak Bluffs

Cassandra

$423 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Oak Bluffs

Donna R.

$343 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Oak Bluffs

$275 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

6. Vineyard Luxury "Yurt"

Oak Bluffs

David C.

$439 nightly

Nov 11 - Nov 12

Total with taxes and fees

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

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

Oak Bluffs

Chris S.

$610 nightly

Nov 20 - Nov 21

Total with taxes and fees

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

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

Oak Bluffs

Eli R.

$557 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

9. < 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.

$796 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

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

Oak Bluffs

Lamar A.

$2,588 nightly

Nov 30 - Dec 1

Total with taxes and fees

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

Oak Bluffs

Sherise M.

$423 nightly

Nov 11 - Nov 12

Total with taxes and fees

12. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

$751 nightly

Nov 11 - Nov 12

Total with taxes and fees

A marina with boats docked along the shore, surrounded by greenery and a sandy beach.

13. Mansion House Inn And Spa

Vineyard Haven

David

$187 nightly

Nov 11 - Nov 12

Total with taxes and fees

A patio with a wooden table and chairs, a hanging flower pot with red and yellow flowers, and a view of the sea with boats in the background.

14. Vineyard Harbor Motel - Private Beach

Vineyard Haven

Joseph

$160 nightly

Nov 18 - Nov 19

Total with taxes and fees

A sandy beach with footprints and seaweed, a clear blue sky, and a row of houses in the background.

15. Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgartown

Lisa

$182 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

16. The Franklin Hotel Martha's Vineyard

Edgartown

Mark

$147 nightly

Nov 24 - Nov 25

Total with taxes and fees

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

17. Faraway Martha's Vineyard

Edgartown

Dylan

$236 nightly

Nov 24 - Nov 25

Total with taxes and fees

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

18. The Coonamessett

Falmouth

Sergio Rodrigo

$91 nightly

Nov 30 - Dec 1

Total with taxes and fees

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

19. Harbor View Hotel

Edgartown

Eryn

$316 nightly

Nov 24 - Nov 25

Total with taxes and fees

20. Red Horse Inn

Falmouth Heights

Thomas

$109 nightly

Nov 11 - Nov 12

Total with taxes and fees

View all properties

Learn more about Oak Bluffs

The colorful gingerbread cottages of the Martha's Vineyard Campground will charm you with their whimsical Victorian details. Take the Flying Horses carousel for a spin, then stroll along Ocean Park's waterfront where locals gather for sunset picnics.

See all hotels in Oak Bluffs

A historic two-story house with a balcony and a porch, surrounded by a well-maintained garden.

Top reviews in Oak Bluffs

Madison Inn

Oak Bluffs

10/10 Excellent

Anonymous traveler

Morgan Hotel

Oak Bluffs

10/10 Excellent

Raymond

Vineyard Harbor Motel - Private Beach

Vineyard Haven

10/10 Excellent

Martina

A beach with clear skies, calm waves, and large rocks.

InnSeason Resorts Captain's Quarters

Falmouth Heights

10/10 Excellent

Crystal

The Franklin Hotel Martha's Vineyard

Edgartown

10/10 Excellent

Kathryn

A residential property with a gravel driveway, a wooden bench, and a house with a shingled exterior.

The Lightkeepers Inn

Edgartown

10/10 Excellent

Anonymous traveler

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

Shore Haven Inn

Falmouth

10/10 Excellent

Nicole

Faraway Martha's Vineyard

Edgartown

10/10 Excellent

Cathy

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgartown

10/10 Excellent

"M"

Red Horse Inn

Falmouth Heights

10/10 Excellent

Meredith

A cozy living room with a fireplace, comfortable seating, and a bookshelf.

The Ashley Inn

Edgartown

10/10 Excellent

Anonymous traveler

The Coonamessett

Falmouth

10/10 Excellent

Gorgeous property right out of the gate from the area where you enter and check-in merging with the space to sit by the fireplace then the beautiful, rustic tavern and stunning event space in addition to the lovely, updated and spacious room just yards away for our overnight stay! Very friendly and kind staff as well! Could not be more impressed and pleased with our stay. Perfect balance of rustic, old Cape Cod charm and modern amenities. Superb!

Holly

A beach with clear blue water, a sandy shore, and a pier with boats. There are blue umbrellas and lounge chairs on the beach.

Falmouth Tides

Falmouth Heights

10/10 Excellent

Luiz

Harbor View Hotel

Edgartown

10/10 Excellent

Anonymous traveler

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

Inn on the Sound

Falmouth Heights

10/10 Excellent

Lisa

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

Vineyard Square Hotel & Suites

Edgartown

10/10 Excellent

Lynn

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

Frederick William House

Falmouth

10/10 Excellent

My friend and I spent 4 nights in this beautiful bed and breakfast. The property is conveniently located on Route 28 in Falmouth. Not only is the house on a bike trail, but you are allowed to use the bikes for free, even to take to the Vinyard, a 40 minute ride by ferry. We went over twice using the Queen Authority first from Falmouth and the Steamship Authority from Woods Hole the next. The Steamship was cheaper and better. But there are really nice beaches nearby. Woods Hole is nearby where...

Elm

An outdoor patio with a fire table, seating, and a table set for a meal.

The Palmer House Inn

Falmouth

10/10 Excellent

My husband and I loved our stay at the antiques-filled Palmer House Inn. We were able to easily walk to the active Main Street and had our choice of excellent restaurants and gift shops to browse. We also walked to the beach (mostly sandy, but with many sharp rocks as you enter the water), rented bikes and rode to a lighthouse, and enjoyed the delicious breakfasts while sitting on the porch in the cooler weather. I would definitely recommend this property to anyone heading to Cape Cod.

Lori

Frequently Asked Questions

What is Oak Bluffs like for a resort vacation?

You deserve to get away, and a resort is just the place to indulge in all the amenities and services you need for a relaxing stay in Oak Bluffs. One of the comfortable resorts in the surrounding area could be just what you're looking for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or fun activities to try.

What's a favorite resort in Oak Bluffs?

Here's our top-rated Oak Bluffs resort: The Island Inn on Martha's Vineyard - Golf resort. Features a seasonal outdoor pool, 3 outdoor tennis courts, and a beach shuttle.

What can I do in Oak Bluffs?

Travelers enjoy exploring the beaches, and have good things to say about the shopping and other activities. Monuments like Trinity Park Tabernacle and East Chop Light are places to learn more about the local history, or you can head to Oak Bluffs Town Beach and Inkwell Beach for some time by the water. Additional attractions in the area include Circuit Avenue and Flying Horses Carousel.

What's the weather like in Oak Bluffs?

The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Oak Bluffs is 47 inches.

What's the best way to get to and around Oak Bluffs?

Fly into Vineyard Haven, MA (MVY-Martha's Vineyard), which is located 5.2 mi (8.3 km) from the heart of the city. Otherwise, you can search for flights to Hyannis, MA (HYA-Barnstable Municipal), which is 20.5 mi (32.9 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

Best Resorts in Oak Bluffs

Bundle & Save

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Upfront pricing

Check prices for these dates

Recommended hotels in Oak Bluffs

1. Madison Inn

2. Morgan Hotel

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

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

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

6. Vineyard Luxury "Yurt"

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

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

9. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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

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

12. Walk to Beach! Oak Bluffs Home & Studio

13. Mansion House Inn And Spa

14. Vineyard Harbor Motel - Private Beach

15. Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

16. The Franklin Hotel Martha's Vineyard

17. Faraway Martha's Vineyard

18. The Coonamessett

19. Harbor View Hotel

20. Red Horse Inn

Learn more about Oak Bluffs

Top reviews in Oak Bluffs

Madison Inn

10/10 Excellent

Frequently Asked Questions

What is Oak Bluffs like for a resort vacation?

What's a favorite resort in Oak Bluffs?

What can I do in Oak Bluffs?

What's the weather like in Oak Bluffs?

What's the best way to get to and around Oak Bluffs?

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