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Oak Bluffs Vacation Rentals

1 - 42 of 44 rentals
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Cape on Forest  - Oak Bluffs, MA Vacation Rental

Cape on Forest

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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Bright Grove - Oak Bluffs, MA Vacation Rental

Bright Grove

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
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Island Sanctuary - Oak Bluffs, MA Vacation Rental

Island Sanctuary

Oak Bluffs, MA
3 Bed 1.5 Bath Sleeps 7
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The Wayland Victorian - Oak Bluffs, MA Vacation Rental

The Wayland Victorian

Oak Bluffs, MA
5 Bed 2 Bath Sleeps 12
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Serenity  - Oak Bluffs, MA Vacation Rental

Serenity

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 4
125 175 175 135 135 135 135 135 175 175 130 130 130 130 130 170 170
The Walker House  - Oak Bluffs, MA Vacation Rental

The Walker House

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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The Samoset  - Oak Bluffs, MA Vacation Rental

The Samoset

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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Oak View Cottage  - Oak Bluffs, MA Vacation Rental

Oak View Cottage

Oak Bluffs, MA
3 Bed 2.5 Bath Sleeps 6
- - - - - - - - - 750 750 750 750 750 750 750 750
Sunset Meadows - Oak Bluffs, MA Vacation Rental

Sunset Meadows

Oak Bluffs, MA
2 Bed 1 Bath Sleeps 4
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Stewart Manor - Oak Bluffs, MA Vacation Rental

Stewart Manor

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
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The Looks Pond Garden House - West Tisbury, MA Vacation Rental
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Seventh Heaven  - Vineyard Haven, MA Vacation Rental

Seventh Heaven

Vineyard Haven, MA
4 Bed 2 Bath Sleeps 9
- - - - - - - - - 195 190 190 190 190 190 235 235
Nature's Pocket  - Vineyard Haven, MA Vacation Rental

Nature's Pocket

Vineyard Haven, MA
3 Bed 3 Bath Sleeps 6
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Pine Street Haven - Edgartown, MA Vacation Rental

Pine Street Haven

Edgartown, MA
4 Bed 3 Bath Sleeps 8
- 195 215 165 165 165 165 160 - - - - 195 220 220 280 280
The Happy Place  - Vineyard Haven, MA Vacation Rental

The Happy Place

Vineyard Haven, MA
4 Bed 1.5 Bath Sleeps 8
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Casita del Amor "Love Cottage" - Edgartown, MA Vacation Rental
125 170 170 120 - - - - - - - - - - - - -
Oak Villa - Edgartown, MA Vacation Rental

Oak Villa

Edgartown, MA
6 Bed 3.5 Bath Sleeps 13
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The CAVU Mansion on Bellevue  - Tisbury, MA Vacation Rental
- - - - - - - - - 195 190 190 190 190 190 245 245
The Blue Cape - Edgartown, MA Vacation Rental

The Blue Cape

Edgartown, MA
3 Bed 2 Bath Sleeps 8
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Lantern Lane - Vineyard Haven, MA Vacation Rental

Lantern Lane

Vineyard Haven, MA
4 Bed 2.5 Bath Sleeps 11
190 225 225 190 190 190 190 190 240 240 190 190 190 190 190 240 240
The Vacation House - Vineyard Haven, MA Vacation Rental

The Vacation House

Vineyard Haven, MA
2 Bed 1 Bath Sleeps 6
115 165 165 120 120 120 120 99 - - 99 120 120 120 120 155 155
Colonial Blue on Whalers Walk - Edgartown, MA Vacation Rental
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Islander's Retreat  - Vineyard Haven, MA Vacation Rental

Islander's Retreat

Vineyard Haven, MA
3 Bed 3.5 Bath Sleeps 9
225 - - 280 290 290 290 290 325 325 290 290 290 290 290 325 325
Briar Patch - Edgartown, MA Vacation Rental

Briar Patch

Edgartown, MA
3 Bed 2 Bath Sleeps 7
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Casa de Reyna - Edgartown, MA Vacation Rental

Casa de Reyna

Edgartown, MA
5 Bed 3.5 Bath Sleeps 8
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The  Eliot Noyes - Chilmark, MA Vacation Rental

The Eliot Noyes

Chilmark, MA
4 Bed 2 Bath Sleeps 8
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The Bird's Nest  - Chilmark, MA Vacation Rental

The Bird's Nest

Chilmark, MA
2 Bed 1 Bath Sleeps 4
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Sweet Island Child - Chilmark, MA Vacation Rental

Sweet Island Child

Chilmark, MA
3 Bed 2 Bath Sleeps 6
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Martha's Nest - Edgartown, MA Vacation Rental

Martha's Nest

Edgartown, MA
3 Bed 2 Bath Sleeps 8
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Island Romance  - Chilmark, MA Vacation Rental

Island Romance

Chilmark, MA
4 Bed 1.5 Bath Sleeps 8
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Tranquility on Great Plains - West Tisbury, MA Vacation Rental
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Off the Radar on Hidden Village Road - West Tisbury, MA Vacation Rental
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Historic Whaling Captain's Home - Falmouth, MA Vacation Rental
165 195 195 165 165 165 165 165 220 220 175 175 175 175 175 250 250
Captain's Cottage - Falmouth, MA Vacation Rental

Captain's Cottage

Falmouth, MA
1 Bed 1 Bath Sleeps 5
125 140 140 115 115 115 115 115 150 150 120 120 120 120 120 155 155
Historic Whaling Captain's Home & Cottage - Falmouth, MA Vacation Rental
255 295 295 235 250 250 250 250 330 330 265 265 265 265 265 365 365
Beauty and the Beach on Chapoquoit Island  - Falmouth, MA Vacation Rental
215 260 - - - 155 - - - - 195 195 195 195 195 280 -
The Green Monstah! - Falmouth, MA Vacation Rental

The Green Monstah!

Falmouth, MA
4 Bed 1.5 Bath Sleeps 12
160 215 215 180 180 180 180 180 225 225 155 155 155 155 155 215 215
"Old Silver" - Falmouth, MA Vacation Rental

"Old Silver"

Falmouth, MA
2 Bed 1 Bath Sleeps 4
155 195 195 150 150 150 150 150 190 190 130 130 130 130 130 175 175
Shady Centerville Tree House - Centerville , MA Vacation Rental

Shady Centerville Tree House

Centerville , MA
4 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
155 195 195 170 170 170 170 170 185 - - - - - - - -
Mill View: La Maison de l'Artiste - Falmouth, MA Vacation Rental
140 180 180 150 150 150 150 150 190 190 140 140 140 140 140 185 185
Stunning Coastal Retreat - Falmouth, MA Vacation Rental

Stunning Coastal Retreat

Falmouth, MA
5 Bed 2.5 Bath Sleeps 12
- - 155 140 140 140 140 140 195 195 150 150 150 150 140 - -
A Slice of Heaven in Falmouth - Falmouth, MA Vacation Rental
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Page 1 of 2

About Oak Bluffs

Oak Bluffs rated 4.8 out of 5 based on 49 reviews Oak bluffs, MA

Beautiful beaches, quaint shops, and cozy restaurants make a getaway to one of our Oaks Bluffs vacation rentals on Martha's Vineyard a can't-miss Massachusetts experience.

Once a part of nearby Edgartown, Oak Bluffs became its own community in 1880 (it was formerly dubbed Cottage City). Named for the oak groves that grew along the bluffs overlooking Nantucket Sound, Oak Bluffs has long been a tourism stronghold. In the 19th century, tourists arrived from the mainland via steamer and shopped, danced, and swam to their hearts' content. Today, thousands of visitors head here each summer to swim in the warm waters of the Sound and to enjoy concerts, art festivals, and other activities throughout the season. 

Things to Do in Oak Bluffs, MA

Oak Bluffs boasts a wealth of attractions, the most notable being the Flying Horses Carousel. This Victorian-era merry-go-round, the nation's oldest, is a National Historic Landmark and delights children and adults from spring to fall. 

The Cottage Museum houses period furnishings and photos of the town from the 19th century. Tour the East Chop Lighthouse, a cast-iron lighthouse built in 1878 - the last lighthouse erected on the island. The Featherstone Center for the Arts features galleries and studios amid six beautiful acres. Enjoy a lecture series or admire the rotating exhibits. 

Outdoor Attractions in Oak Bluffs, MA

Oak Bluffs, like Edgartown, boasts a plethora of beautiful beaches and preserves. East Chop Beach is a small beach near the harbor with a great view of Nantucket Sound. Oak Bluffs Town Beach features calm water, perfect for novice swimmers and families. Joseph Sylvia Beach offers miles of soft sand and is a windsurfer's paradise. 

Hikers and bikers look no further than the beautiful parks, farms, and preserves in town. Sailing Camp Park features 15 acres of preserved land with great views of the lagoon. At 18 acres, Featherstone Farm boasts a network of tranquil wooded trails for wandering. Farm Pond Preserve displays a wealth of marshlands and woodland trails connected to Trade Wind Field Preserve; the latter offers nearly 72 lush acres of woodlands and fields. Pecoy Point Preserve affords visitors 17 acres of marsh and woodland, as well as trails along peaceful Sengekontacket Pond.

From scenic marshlands to quaint mom-and-pop shops and romantic eateries, our Oak Bluffs vacation rentals offer the perfect home base for enjoying this charming town - and all of Martha's Vineyard.  

Photo credit: AR Pictures via Shutterstock

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