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148 Rentals
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Featured 
$500/night
Near Beach & Harbor Oak Bluffs | 001
7 Gorham Avenue, Oak Bluffs, MA 02558- 4 Bedrooms
- 2 Baths
- 6 Guests
- Cottage
Featured
$475/night
In Town Victorian with large back yard | 69
77 Pennacook Avenue, Oak Bluffs MA 02557- 5 Bedrooms
- 1.5 Baths
- 6 Guests
- Cottage
Featured
$571/night
Oak Bluffs 5 BR/ 2BA close to harbor with A/C! | 39
58 New York Avenue, Oak Bluffs, MA 02557- 5 Bedrooms
- 2 Baths
- House
Featured
$3,571/night
Squibnocket Retreat/280
18 Spruce Gate Road- 4 Bedrooms
- 4. Baths
- 8 Guests
- House
Featured
$929/night
One block to the Beach in Oak Bluffs Sleeps 10 | 237
15 Pequot Avenue, Oak Bluffs, MA 02557- 5 Bedrooms
- 3.5 Baths
- 10 Guests
- House
Featured
$629/night
A classic vineyard beach house with water views /277
220 Newton Ave, Oak Bluffs, MA- 2 Bedrooms
- 1 Baths
- 4 Guests
- Cottage
Featured
$886/night
Vineyard Haven Beauty/281
44 Edgartown Road- 4 Bedrooms
- 2.5 Baths
- 7 Guests
Featured
$572/night
Oak Bluffs -Waterview Home on the lagoon | 102
12 Mae Avenue, Oak Bluffs- 3 Bedrooms
- 2 Baths
- 8-10 Guests
- House
$715/night
Nashawena Park Steps from Inkwell Beach | 34
38 Nashawena Avenue, Oak Bluffs. MA 02557- 4 Bedrooms
- 2 Baths
- 8 Guests
- House
$343/night
Walk to private Gull Landing lagoon beach, bike to town, enjoy quiet !/270
51 Gull Landing, Oak Bluffs, MA 02557- 3 Bedrooms
- 2 Baths
- 7 Guests
- House
$643/night
Waterfront 4 Bedroom in Sengy | 263
12 Wood Duck Way, Oak Bluffs, MA 02557- 4 Bedrooms
- 3 Baths
- 8 Guests
- House
$743/night
Newer home in Vineyard Haven with cental a/c and close to town | 228
51 Amelia's Crossing, Vineyard Haven, MA 02568- 3 Bedrooms
- 3 Baths
- 6-8 Guests
- House
$372/night
MVCMA Campground cottage walk to beach & town | 152
5 Rock Ave, Oak Bluffs, MA 02557, USA- 4 Bedrooms
- 2 Baths
- 8 Guests
- Cottage
$519/night
Custom Built home with Farmer’s porch in East Chop | 55
5 Elmwood Avenue, Oak Bluffs, MA 02557- 3 Bedrooms
- 2 Baths
- 6 Guests
- House
$643/night
Seaview Condo- Sleeps 5! | 35
2 Pennacook Avenue, Oak Bluffs, MA 02557- 2 Bedrooms
- 2 Baths
- 5 Guests
- Condo
$2,143/night
Ocean Park Overlooking Nantucket Sound in Oak Bluffs | 121
101 Ocean Avenue, Oak Bluffs, MA 02557- 7 Bedrooms
- 4.5 Baths
- 14 Guests
- House
$472/night
Chilmark Cape -Select Ferry Tickets available | 68
25 North Road, Chilmark, MA 02575- 4 Bedrooms
- 2 Baths
- 8 Guests
- House
$500/night
Katama Colonial | 144
34 Schoolhouse Road, Edgartown, MA 02539- 3 Bedrooms
- 2 Baths
- 8 Guests
- House
$1,286/night
LOCATION! LOCATION! LOCATION! 4 Bedroom Overlooking Nantucket Sound! | 262
115 Seaview Avenue, Oak Bluffs, M- 4 Bedrooms
- 4.5 Baths
- 10 Guests
- House
$500/night
Campground Cottage Once Summer home of Ulysses S. Grant | 17
10 Clinton Avenue, Oak Bluffs, MA 02557- 5 Bedrooms
- 1 Baths
- 8 Guests
- Cottage