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Oak Bluffs Vacation Rentals

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Island Inn - 36G - Oak Bluffs, MA Vacation Rental

Island Inn - 36G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- - 99 99 99 118 118 99 99 156 168 178 194 188 168 145 144
Island Inn - 38G - Oak Bluffs, MA Vacation Rental

Island Inn - 38G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- 87 88 84 - - - 89 92 140 144 - - - 160 145 144
Island Inn - 45G - Oak Bluffs, MA Vacation Rental

Island Inn - 45G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
99 110 111 111 111 133 133 120 116 188 198 189 - - 160 131 127
Island Inn - 43G - Oak Bluffs, MA Vacation Rental

Island Inn - 43G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
99 110 111 111 111 133 133 120 116 175 179 - - 179 187 163 162
Island Inn - 31G - Oak Bluffs, MA Vacation Rental

Island Inn - 31G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
84 87 88 89 84 - - 85 - - - - - - 137 - -
Island Inn - 46G - Oak Bluffs, MA Vacation Rental

Island Inn - 46G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - 99 99 99 - - - 110 188 198 199 216 209 187 146 141
Island Inn - 37G - Oak Bluffs, MA Vacation Rental

Island Inn - 37G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
99 99 99 99 99 118 118 99 99 156 168 169 - - 160 145 144
Island Inn - 16D - Oak Bluffs, MA Vacation Rental

Island Inn - 16D

Oak Bluffs, MA
1 Bed 1 Bath Sleeps 4
71 75 75 76 72 - - 76 79 119 130 130 - - 136 123 122
Island Inn - 12D - Oak Bluffs, MA Vacation Rental

Island Inn - 12D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - 63 67 63 - - 68 69 99 113 114 - - 119 108 108
Island Inn - 42G - Oak Bluffs, MA Vacation Rental

Island Inn - 42G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
- 128 128 128 128 151 151 137 134 197 201 - - 199 211 185 185
Island Inn - 30G - Oak Bluffs, MA Vacation Rental

Island Inn - 30G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
99 99 99 99 99 118 118 99 99 156 168 178 194 188 168 145 137
Island Inn - 6B - Oak Bluffs, MA Vacation Rental

Island Inn - 6B

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- 69 73 74 74 88 88 79 77 116 126 127 - 120 125 108 108
Island Inn - 51G - Oak Bluffs, MA Vacation Rental

Island Inn - 51G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
99 99 99 99 99 - - - 99 157 169 170 - - 178 163 162
Island Inn - 25F - Oak Bluffs, MA Vacation Rental

Island Inn - 25F

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
63 66 66 63 - - - 64 - - - 108 - - 119 99 99
Island Inn - 33G - Oak Bluffs, MA Vacation Rental

Island Inn - 33G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- 92 99 99 99 99 - - - - - - - - - 138 144
Island Inn - 40G - Oak Bluffs, MA Vacation Rental

Island Inn - 40G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- - - 99 99 - - - 99 157 161 - - 179 187 163 162
Island Inn - 35G - Oak Bluffs, MA Vacation Rental

Island Inn - 35G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
79 - - - - - - 89 92 140 151 152 - - 160 145 144
Island Inn - 41G - Oak Bluffs, MA Vacation Rental

Island Inn - 41G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
121 128 128 128 128 151 151 137 134 197 212 221 239 232 211 185 185
Island Inn - 18D - Oak Bluffs, MA Vacation Rental

Island Inn - 18D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- 69 73 74 74 88 88 79 77 116 126 127 - - 119 108 108
Island Inn - 17D - Oak Bluffs, MA Vacation Rental

Island Inn - 17D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
59 - - - - - - 68 69 99 113 114 - - 107 99 99
Island Inn - 39G - Oak Bluffs, MA Vacation Rental

Island Inn - 39G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
99 99 99 99 99 118 118 99 99 156 168 169 - - - 138 144
Island Inn - 3B - Oak Bluffs, MA Vacation Rental

Island Inn - 3B

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - 68 69 113 113 - - 120 125 99 99
Island Inn - 10C - Oak Bluffs, MA Vacation Rental

Island Inn - 10C

Oak Bluffs, MA
1 Bed 1 Bath Sleeps 2
79 83 83 84 84 112 112 89 87 126 - - - - - 117 122
Island Inn - 34G - Oak Bluffs, MA Vacation Rental

Island Inn - 34G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- 83 88 89 84 - - 99 99 156 168 178 194 188 168 145 144
Island Inn - 7C - Oak Bluffs, MA Vacation Rental

Island Inn - 7C

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- 73 73 74 74 88 88 79 77 116 126 127 - 120 125 108 108
Island Inn - 48G - Oak Bluffs, MA Vacation Rental

Island Inn - 48G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
121 128 128 128 128 151 151 137 134 212 221 221 239 232 211 167 163
Island Inn - 29G - Oak Bluffs, MA Vacation Rental

Island Inn - 29G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
- - - - - 124 124 99 99 156 168 169 - - 160 145 144
Island Inn - 9C - Oak Bluffs, MA Vacation Rental

Island Inn - 9C

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
59 - - - - - - 68 69 99 113 114 - - - 99 108
Island Inn - 5B - Oak Bluffs, MA Vacation Rental

Island Inn - 5B

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- 69 73 74 74 76 - - 65 99 113 114 - - - 99 108
Island Inn - 15D - Oak Bluffs, MA Vacation Rental

Island Inn - 15D

Oak Bluffs, MA
1 Bed 1 Bath Sleeps 4
- - - 72 72 - - 76 79 119 123 - - - 136 123 122
Island Inn - 50G - Oak Bluffs, MA Vacation Rental

Island Inn - 50G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
109 109 - - - 136 143 137 134 212 210 - - - - 159 163
Island Inn - 13D - Oak Bluffs, MA Vacation Rental

Island Inn - 13D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
63 66 66 67 63 - - 68 69 99 108 - - - 119 108 108
Island Inn - 47G - Oak Bluffs, MA Vacation Rental

Island Inn - 47G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- 99 111 111 111 133 133 120 116 188 198 189 - - 178 146 141
Island Inn - 32G - Oak Bluffs, MA Vacation Rental

Island Inn - 32G

Oak Bluffs, MA
1 Bed 1.5 Bath Sleeps 6
99 99 99 99 99 118 118 99 99 156 168 169 - - 160 145 144
Island Inn - 14D - Oak Bluffs, MA Vacation Rental

Island Inn - 14D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - 68 69 99 113 114 - - 119 108 108
Island Inn - 20D - Oak Bluffs, MA Vacation Rental

Island Inn - 20D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
69 73 73 74 74 88 88 79 77 116 126 133 145 140 125 108 108
Island Inn - 21E - Oak Bluffs, MA Vacation Rental

Island Inn - 21E

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 6
- 114 - - 110 - - - - - 195 - - - 195 160 155
Island Inn - 4B - Oak Bluffs, MA Vacation Rental

Island Inn - 4B

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
63 66 66 67 63 - - 68 69 99 113 114 - 120 125 108 108
Island Inn - 19D - Oak Bluffs, MA Vacation Rental

Island Inn - 19D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
69 73 73 74 74 88 88 79 77 116 126 127 - - 119 108 108
Island Inn - 11D - Oak Bluffs, MA Vacation Rental

Island Inn - 11D

Oak Bluffs, MA
0 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - 119 108 108
Island Inn - 44G - Oak Bluffs, MA Vacation Rental

Island Inn - 44G

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 6
- 110 111 111 111 133 133 120 116 188 198 199 185 - - 139 141
Island Inn - 49G - Oak Bluffs, MA Vacation Rental

Island Inn - 49G

Oak Bluffs, MA
2 Bed 2 Bath Sleeps 4
- - - - - 144 151 137 134 212 221 210 - - 200 167 163
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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