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Oak Bluffs Vacation Rentals

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Island Inn - 47G - Oak Bluffs, MA Vacation Rental

Island Inn - 47G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - 261 274 274 309 444
Island Inn - 39G - Oak Bluffs, MA Vacation Rental

Island Inn - 39G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - 220 - - - 267 407
Island Inn - 38G - Oak Bluffs, MA Vacation Rental

Island Inn - 38G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - - - 236 281 407
Island Inn - 45G - Oak Bluffs, MA Vacation Rental

Island Inn - 45G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - - - 261 309 444
Island Sanctuary - Oak Bluffs, MA Vacation Rental

Island Sanctuary

Oak Bluffs, MA
3 Bed 1.5 Bath Sleeps 7
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Island Inn - 42G - Oak Bluffs, MA Vacation Rental

Island Inn - 42G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
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Island Inn - 48G - Oak Bluffs, MA Vacation Rental

Island Inn - 48G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
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Island Inn - 40G - Oak Bluffs, MA Vacation Rental

Island Inn - 40G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - 242 - - 261 309 444
Island Inn - 15D - Oak Bluffs, MA Vacation Rental

Island Inn - 15D

Oak Bluffs, MA
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - 262 323
Island Inn - 33G - Oak Bluffs, MA Vacation Rental

Island Inn - 33G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - 249 249 249 281 346
Island Inn - 7C - Oak Bluffs, MA Vacation Rental

Island Inn - 7C

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
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Island Inn - 49G - Oak Bluffs, MA Vacation Rental

Island Inn - 49G

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

Bright Grove

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - 277 293 325 -
Island Inn - 17D - Oak Bluffs, MA Vacation Rental

Island Inn - 17D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - 164 - - - 199 258
Island Inn - 32G - Oak Bluffs, MA Vacation Rental

Island Inn - 32G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
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Island Inn - 26F - Oak Bluffs, MA Vacation Rental

Island Inn - 26F

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
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Island Inn - 24F - Oak Bluffs, MA Vacation Rental

Island Inn - 24F

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
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Island Inn - 37G - Oak Bluffs, MA Vacation Rental

Island Inn - 37G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
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Island Inn - 44G - Oak Bluffs, MA Vacation Rental

Island Inn - 44G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
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#OB Pool House - Oak Bluffs, MA Vacation Rental

#OB Pool House

Oak Bluffs, MA
5 Bed 4.5 Bath Sleeps 10
- - - - - - - - - - 974 952 857 857 857 993 1526
Island Inn - 16D - Oak Bluffs, MA Vacation Rental

Island Inn - 16D

Oak Bluffs, MA
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - 187 - - - 227 346
Island Inn - 11D - Oak Bluffs, MA Vacation Rental

Island Inn - 11D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - 164 - - - - -
Island Inn - 13D - Oak Bluffs, MA Vacation Rental

Island Inn - 13D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - 289
Island Inn - 31G - Oak Bluffs, MA Vacation Rental

Island Inn - 31G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - - - - 227 -
Island Inn - 51G - Oak Bluffs, MA Vacation Rental

Island Inn - 51G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - 421
Clyde's Nook  - Oak Bluffs, MA Vacation Rental

Clyde's Nook

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
- - - - - - - - - - 354 345 307 307 307 361 570
Oak Bluffs Beauty - Oak Bluffs, MA Vacation Rental

Oak Bluffs Beauty

Oak Bluffs, MA
4 Bed 3 Bath Sleeps 10
- - - - - - - - - - - 407 358 - - - -
Island Inn - 12D - Oak Bluffs, MA Vacation Rental

Island Inn - 12D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - 289
Island Inn - 50G - Oak Bluffs, MA Vacation Rental

Island Inn - 50G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - 451
Hidden Among the Trees - Oak Bluffs, MA Vacation Rental

Hidden Among the Trees

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
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Island Inn - 4B - Oak Bluffs, MA Vacation Rental

Island Inn - 4B

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
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Cape on Forest  - Oak Bluffs, MA Vacation Rental

Cape on Forest

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - - - - 657
Island Inn - 35G - Oak Bluffs, MA Vacation Rental

Island Inn - 35G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - 201 - - 227 -
Island Inn - 43G - Oak Bluffs, MA Vacation Rental

Island Inn - 43G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - - - - 293 444
The Wayland Victorian - Oak Bluffs, MA Vacation Rental

The Wayland Victorian

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 10
- - - - - - - - - - 580 679 593 - - - -
Island Inn - 25F - Oak Bluffs, MA Vacation Rental

Island Inn - 25F

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
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Island Inn - 41G - Oak Bluffs, MA Vacation Rental

Island Inn - 41G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - 243 - - 451
Island Inn - 3B - Oak Bluffs, MA Vacation Rental

Island Inn - 3B

Oak Bluffs, MA
0 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
- - - - - - - - - - - 300 267 - - - -
Island Inn - 46G - Oak Bluffs, MA Vacation Rental

Island Inn - 46G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - 421
Island Inn - 21E - Oak Bluffs, MA Vacation Rental

Island Inn - 21E

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
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Island Inn - 23F - Oak Bluffs, MA Vacation Rental

Island Inn - 23F

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - 158 178 -
Page 1 of 3

About Oak Bluffs

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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