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Oak Bluffs Vacation Rentals

1 - 42 of 43 rentals
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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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The Walker House  - Oak Bluffs, MA Vacation Rental

The Walker House

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

The Wayland Victorian

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

Oak View Cottage

Oak Bluffs, MA
3 Bed 2.5 Bath Sleeps 6
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Serenity  - Oak Bluffs, MA Vacation Rental

Serenity

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 4
125 125 155 155 130 130 130 130 130 165 165 130 130 130 130 130 165
The Samoset  - Oak Bluffs, MA Vacation Rental

The Samoset

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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Sunset Meadows - Oak Bluffs, MA Vacation Rental

Sunset Meadows

Oak Bluffs, MA
2 Bed 1 Bath Sleeps 4
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The Looks Pond Garden House - West Tisbury, MA Vacation Rental
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Nature's Pocket  - Vineyard Haven, MA Vacation Rental

Nature's Pocket

Vineyard Haven, MA
3 Bed 3 Bath Sleeps 6
270 270 320 320 290 290 290 290 290 340 340 290 290 290 290 290 340
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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Seventh Heaven  - Vineyard Haven, MA Vacation Rental

Seventh Heaven

Vineyard Haven, MA
4 Bed 2 Bath Sleeps 9
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Tranquility on Great Plains - West Tisbury, MA Vacation Rental
160 160 195 195 170 170 170 170 170 220 220 170 170 170 170 170 220
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
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Pine Street Haven - Edgartown, MA Vacation Rental

Pine Street Haven

Edgartown, MA
4 Bed 3 Bath Sleeps 8
140 130 - - - - - - - 215 225 160 160 160 160 160 225
The Blue Cape - Edgartown, MA Vacation Rental

The Blue Cape

Edgartown, MA
3 Bed 2 Bath Sleeps 8
120 120 180 180 125 125 125 135 135 195 195 135 135 135 135 135 195
Casita del Amor "Love Cottage" - Edgartown, MA Vacation Rental
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Colonial Blue on Whalers Walk - Edgartown, MA Vacation Rental
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Lantern Lane - Vineyard Haven, MA Vacation Rental

Lantern Lane

Vineyard Haven, MA
4 Bed 2.5 Bath Sleeps 11
185 185 235 235 195 195 195 195 195 250 250 195 195 195 195 195 250
The Vacation House - Vineyard Haven, MA Vacation Rental

The Vacation House

Vineyard Haven, MA
2 Bed 1 Bath Sleeps 6
99 99 145 145 115 115 115 115 115 155 155 115 115 115 115 115 155
Islander's Retreat  - Vineyard Haven, MA Vacation Rental

Islander's Retreat

Vineyard Haven, MA
3 Bed 3.5 Bath Sleeps 9
285 285 320 320 295 295 295 295 295 340 340 295 295 295 295 295 340
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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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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The Bird's Nest  - Chilmark, MA Vacation Rental

The Bird's Nest

Chilmark, MA
2 Bed 1 Bath Sleeps 4
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Off the Radar on Hidden Village Road - West Tisbury, MA Vacation Rental
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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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Captain's Cottage - Falmouth, MA Vacation Rental

Captain's Cottage

Falmouth, MA
1 Bed 1 Bath Sleeps 5
99 99 150 150 115 115 115 160 160 195 195 160 160 160 160 160 195
The Green Monstah! - Falmouth, MA Vacation Rental

The Green Monstah!

Falmouth, MA
4 Bed 1.5 Bath Sleeps 12
220 220 255 255 235 235 235 185 185 235 235 185 185 185 185 185 235
Beauty and the Beach on Chapoquoit Island  - Falmouth, MA Vacation Rental
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Stunning Coastal Retreat - Falmouth, MA Vacation Rental

Stunning Coastal Retreat

Falmouth, MA
5 Bed 2.5 Bath Sleeps 12
140 140 175 175 145 155 155 160 160 225 215 - - - - - -
"Old Silver" - Falmouth, MA Vacation Rental

"Old Silver"

Falmouth, MA
2 Bed 1 Bath Sleeps 4
130 130 170 170 135 135 135 160 160 195 195 160 160 160 160 160 195
Shady Centerville Tree House - Centerville , MA Vacation Rental

Shady Centerville Tree House

Centerville , MA
4 Bed 2.5 Bath Sleeps 8 (6 Adults Max)
215 215 245 245 225 225 225 175 175 225 225 175 175 175 175 175 225
Mill View: La Maison de l'Artiste - Falmouth, MA Vacation Rental
130 130 170 170 135 135 135 135 135 180 180 135 135 135 135 135 180
Historic Whaling Captain's Home - Falmouth, MA Vacation Rental
700 700 700 700 700 700 700 700 700 700 700 700 700 700 700 700 700
Historic Whaling Captain's Home & Cottage - Falmouth, MA Vacation Rental
750 750 750 750 750 750 750 750 750 750 750 750 750 750 750 750 750
A Slice of Heaven in Falmouth - Falmouth, MA Vacation Rental
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Hyannis Port Haven - Hyannis, MA Vacation Rental

Hyannis Port Haven

Hyannis, MA
4 Bed 3 Bath Sleeps 7
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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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