This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Oak Bluffs Vacation Rentals Show this location only Back to top
- Stunning, Immaculate and Enormous, Summer at This 6000 Sqft Beach Home! 6BR/3BA – Sleeps 12 – Oak Bluffs #133568ha
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Luxury Loft Historic Center Oak Bluffs
5BR+/2BA
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Sleeps 7-11
– Oak Bluffs #309975
$2500- $5000
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Waterview, Intown, Walk to Beach, Ac, 6 Plus Bedroom/4 Bath
6BR/4BA
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Sleeps 16-18
– Oak Bluffs #458142
$700 per night 3 night min stay
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Updated & Elegant, in-Town Waterview Victorian. 1 Block from Beach. Big Porch.
5BR/2BA
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Sleeps 11
– Oak Bluffs #141191ha
$350 - $686 per night 2-7 night min stay
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Walk to Beach, Town and Park from Gorgeous Martha's Vineyard Home
6BR/2BA
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Sleeps 10
– Oak Bluffs #221408
$1200 - $5200 per week
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Beautiful Home Close to Beach and Town 3BR/2BA – Sleeps 6 – Oak Bluffs #235942
Special offer 20% off in July, September and on
Jun 15, 2013 to Dec 31, 2013
$257 - $310 per night - Breathtaking Waterviews with Private Beach - Harbour House 4BR/2BA – Sleeps 8 – Oak Bluffs #114788
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Beautiful, Bright and Beachy Cottage; Walk to Town and Beach!
2BR+/1BA
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Sleeps 4-5
– Oak Bluffs #229848
$1295 - $2100 per week 7 night min stay
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Ocean Park- Featured in NY Times, Renovated, Central Air, Wifi
6BR+/3BA
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Sleeps 12-14
– Oak Bluffs #271261
$3,000- $13,000/wk
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Lovely 3 Bedrm, 3 Bath Home W/Ac;Steps to Lagoon & Walk to Town
3BR+/3BA
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Sleeps 6
– Oak Bluffs #343277
$1,500- $3,000/wk; $550.00/nt min 3 nt
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July 15-July 21 $3000.Modern Home W/ Private Beach Access.Spacious,Bright.
4BR+/2BA
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Sleeps 8-9
– Oak Bluffs #288246
$1600- $3500/wk
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Beach, Town, and Tennis
6BR/2BA
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Sleeps 15
– Oak Bluffs #43151
$1500- $5250/wk
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Big Victorian Beach House and Cottage. Steps to Beach & Town
5BR+/2BA
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Sleeps 10
– Oak Bluffs #367550
$4004 - $5005 per week 7 night min stay
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Original Pratt House Built in 1866 with Ocean View of the Inkwell Beach
5BR/2BA
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Sleeps 10
– Oak Bluffs #288060
$5600 - $5800 per week
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Walk to Beach and Town. Large Renovated House.
7BR+/4BA
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Sleeps 14-16
– Oak Bluffs #338780
From $3200/wknd
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Sunny Large House, Quiet Street, Short Walk to Town and Beaches
4BR/2BA
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Sleeps 8
– Oak Bluffs #252977ha
$143 - $557 per night
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Great Family House- 2 Minute Walk to Beaches and Town!
5BR+/5BA
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Sleeps 2-15
– Oak Bluffs #311762
$900- $5200
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1870 Renovated Victorian Beach House in the Heart of East Chop
8BR+/3BA
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Sleeps 16-20
– Oak Bluffs #235781
$3500- $6500/wk
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Beautifully Restored Home on Ocean Park One Block from Beach
7BR/4BA
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Sleeps 17
– Oak Bluffs #300138
$10,000 per week 7 night minimum
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Central Air, 6+ Bedroom, 6.5 Bath, Private Association Beach
6BR+/6.5BA
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Sleeps 18-22
– Oak Bluffs #288874
$4000- $10800/wk
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In-Town Victorian, Walk to Beach, Former B and B
9BR/7BA
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Sleeps 18-24
– Oak Bluffs #311763
$900- $7200/wk
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Waterfront, Lagoon Pond, 150' Private Beach. Beautiful Sunsets
3BR+/2.75BA
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Sleeps 9-10
– Oak Bluffs #394700
From $2,800 - $4,500.00/wk
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Perfect Location! in Town, Six Bedroom, Six Bath, with a/C
6BR+/6BA
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Sleeps 20
– Oak Bluffs #399624
$900- $6400
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2013 Fall Getaways - Now Booking!
4BR/2BA
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Sleeps 8
– Oak Bluffs #413958
$900- $3400
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Water View in Town, Located on Beautiful Ocean Park
4BR+/1BA
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Sleeps 12
– Oak Bluffs #365854
$1500- 3000 wk
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Luxury Home with Water Views in Farm Neck! Ob523
5BR/4BA
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Sleeps 8
– Oak Bluffs #3250419ha
$7500 - $10900 per week
- Chickawaukee Two 2BR/1BA – Sleeps 4 – Oak Bluffs #3221391ha
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Just Opened up Fireworks Weekend, August 15-18. Great Location. Ac, New Home
4BR+/3BA
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Sleeps 9
– Oak Bluffs #342749
$350 - $625 per night 2-7 night min stay
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Ob Watrfront 4BR+Stdio. Quiet/Walk to Town. Beachy, Grt Vu's.
4BR+/2BA
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Sleeps 10
– Oak Bluffs #101782
$750- $5000/wk
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Contemporary Luxury Open-Air Loft in the Heart of the Arts District
3BR/3BA
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Sleeps 6
– Oak Bluffs #242039
$2000 - $3750 per week
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Hilltop Waterview Home, 5BR with Universal (Handicap) Access
5BR+/3BA
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Sleeps 10-13
– Oak Bluffs #176599
$2900- $3500/wk US or Canadian Dollars
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Family-Friendly, Island Retreat with Luxurious Amenities
4BR+/5BA
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Sleeps 10-12
– Oak Bluffs #3508963ha
$7800 per week 7 night min stay
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Location, Location, Location!
4BR+/2BA
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Sleeps 8
– Oak Bluffs #59668
$900- $2900/wk
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Location! Harborfront with Small Private Beach!
3BR/2BA
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Sleeps 6
– Oak Bluffs #347502
$1995- $4200/wk
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Waterview Farms Contemporary Adjacent to Farm Neck Golf Course
4BR+/3BA
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Sleeps 8-10
– Oak Bluffs #402797
$2,200 to $2,700/wk
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Waterview Farms, Prime Bike Trails, Martha's Vineyard! Ob501
4BR/3BA
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Sleeps 8
– Oak Bluffs #3198072ha
$2200 - $3300 per week
- Harthaven Waterfront- Ob527 6BR/2BA – Sleeps 11 – Oak Bluffs #3198105ha
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Nashawena Park Oak Bluffs Martha's Vineyard! Ob509
3BR/2BA
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Sleeps 6
– Oak Bluffs #3198080ha
$3050 per week
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Ask About June Specials!
2BR+/2BA
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Sleeps 4
– Oak Bluffs #357299
$1,600 - 1,700/wk
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Charming Six Bedroom Waterview East Chop Victorian in Excellent Location
6BR/1BA
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Sleeps 10
– Oak Bluffs #105316ha
$357 - $557 per night
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Executive Modern Oceanview Hilltop Home with Spectacular Sunrises
4BR+/4BA
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Sleeps 9
– Oak Bluffs #395843ha
$650 - $1500 per night 2-7 night min stay
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Spectacular Waterviews, Private Waterfront, Oceanview Villa
3BR/2BA
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Sleeps 6
– Oak Bluffs #164102
$1800 - $2600 per week
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Perfect Location! by Beach, Harbor & Town! Renovated Gingerbread House & Garden
2BR+/2BA
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Sleeps 4-8
– Oak Bluffs #3496344ha
$350 - $570 per night 2-7 night min stay
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Ocean View Cottage, Private Waterfront , Adjacent to Farm Neck 3BR/3BA – Sleeps 6 – Oak Bluffs #124998
Special offer Oceanview 3BR Cottage $2100 includes car ferry reservation
Sep 1, 2013 to Sep 8, 2013
$1700- $2775 per week -
Exquisite East Chop Waterview Home/Swimspa Labor Day Week Available!
6BR+/4BA
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Sleeps 15
– Oak Bluffs #338384
$8505 per week 7 night min stay
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Dreamy Waterfront Beach Cottage in East Chop on Mv
3BR+/1BA
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Sleeps 6-7
– Oak Bluffs #107969
3000- 5000
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Great Family 6 Bedroom House on the Hill Overlooking Oak Bluff Harbor 6BR+/2BA – Sleeps 9-10 – Oak Bluffs #301726
Special offer 6 Bedroom House Overlooking the Harbor for the 4th of July!
Jun 30, 2013 to Jul 7, 2013
$3200- $4700/wk -
One Level Home in Quiet Cul De Sac. Walk to Lagoon and Main St
3BR/2BA
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Sleeps 6
– Oak Bluffs #341865
$2100 per week 7 night min stay
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Executive Oceanview Hilltop Home with Spectacular Sunrises.
4BR+/4BA
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Sleeps 8-10
– Oak Bluffs #361199
$857 - $1000 per night 2-7 night min stay
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Private Beach Access in Great Neighborhood
3BR/2BA
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Sleeps 6
– Oak Bluffs #249612
$2000 - $2800 per week 7 night min stay
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Perfect for Family, Friends, or a Romantic Getaway
4BR/2BA
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Sleeps 7
– Oak Bluffs #84255
$800- $2400/wk
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1.5 Miles to Town and Beach! 2BR/2BA Sleeps 6. Oak Bluffs
2BR+/2BA
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Sleeps 4-6
– Oak Bluffs #303168
$1904 per week 7 night min stay
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Clean & Cozy Cape Style Home Close to Town
3BR+/2BA
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Sleeps 6-8
– Oak Bluffs #274048
$186 - $300 per night 2-7 night min stay
- Beautiful 3BR/2/Bath Walk to Private Lagoon Beach Porch 3BR/2BA – Sleeps 6 – Oak Bluffs #345781
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Gingerbread Cottage - Harbor View
5BR+/1BA
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Sleeps 11-12
– Oak Bluffs #349343
$2700 per week 7 night min stay
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Sweet Little Space
2BR/2BA
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Sleeps 4
– Oak Bluffs #236250
$1500- $1850/wk
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In-Town Victorian House & Cottage, Walk to Beach, Ferry & Town
5BR/3BA
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Sleeps 9
– Oak Bluffs #239847
$2200- $3600/wk
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Location! Location! Location! Vintage Vineyard Cottage
4BR/2BA
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Sleeps 8
– Oak Bluffs #353500
$1950.00- $2800.00 wk
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Cozy, Clean, Bikes, Kayaks, Laundry, Near Bike Path and Town
3BR+/1BA
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Sleeps 6-9
– Oak Bluffs #240448
$215 - $255 per night 2-7 night min stay
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Charming Island House-Close to Ginger Bread Cottages, Beaches, Shops..
3BR/2BA
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Sleeps 8
– Oak Bluffs #937169ha
$1700 - $2500 per week
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Impeccable East Chop Cottage
2BR+/1BA
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Sleeps 5
– Oak Bluffs #356558
$1400- $2200/wk
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Beautiful Cozy Colonial Short Walk to Town
3BR/2.5BA
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Sleeps 6
– Oak Bluffs #115086
$1500- $2050/wk
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Waterfront Home in Oak Bluffs – Walk to Town and Beach
4BR+/1BA
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Sleeps 8
– Oak Bluffs #401921
June $4000, July $4500-5000, Aug $5000
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Lagoon Pond
3BR/2BA
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Sleeps 4-6
– Oak Bluffs #451916
$375 - $400 per night 6-7 night min stay
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East Chop Victorian Wraparound Porch Walk to Town
5BR/2BA
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Sleeps 10
– Oak Bluffs #357987
$500 per night 2 night min stay
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Charming Light Filed Home on Bike Path and Close to Beach
3BR/2BA
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Sleeps 6-7
– Oak Bluffs #462367
$1200- $3000/wk
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Picture-Perfect Storybook Gingerbread Cottage
2BR+/1BA
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Sleeps 6
– Oak Bluffs #391092
$1500- $1800/wk
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Oak Bluffs Rental, Tranquil Neighborhood Ob502
3BR/2BA
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Sleeps 6
– Oak Bluffs #3198073ha
$1500 - $1800 per week
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Oceanfront Cottage on Nantucket Sound! Ob529
2BR/1BA
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Sleeps 6
– Oak Bluffs #3198107ha
$6875 per week
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Waterview Seaview Condos #203! Ob518
2BR/2BA
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Sleeps 4
– Oak Bluffs #3198097ha
$2300 - $2800 per week
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Seaview Condo #204 in the Heart of Oak Bluffs! Ob519
2BR/2BA
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Sleeps 4
– Oak Bluffs #3198098ha
$2300 - $2800 per week
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Waterview Seaview Condo #304- Ob517
2BR/2BA
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Sleeps 4
– Oak Bluffs #3198095ha
$2300 - $2800 per week
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Oak Bluffs in-Town Rental, Cinderella Cottage! Ob503
4BR/2BA
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Sleeps 8
– Oak Bluffs #3198075ha
$3100 - $5300 per week
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651-Lovely Home Centrally Located to Town & Beach
3BR+/1BA
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Sleeps 8
– Oak Bluffs #3019365ha
$2850 - $3450 per week
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1611 - 2012 Colonial Renovation in Oak Bluffs
5BR/3.5BA
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Sleeps 13
– Oak Bluffs #3019695ha
$2500 - $4850 per week
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Lagoon Waterview, Central Ac, 200 Yards to Private Assoc Lagoon Beach...
3BR/2BA
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Sleeps 6
– Oak Bluffs #942169ha
$2300 - $3500 per week
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East Chop - Walk to Town, Wifi, Central a/C
5BR/2BA
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Sleeps 8
– Oak Bluffs #942594ha
$3050 - $4950 per week
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Classic East Chop Summer Home, Wifi Internet
6BR/4BA
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Sleeps 10
– Oak Bluffs #942466ha
$3200 - $4200 per week
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East Chop, Waterfront, Wifi Internet
5BR/5BA
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Sleeps 9
– Oak Bluffs #942452ha
$6300 - $7800 per week
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Gorgeous Ocean View Cottage Home, Ink Well Beach Across Street, Walk T...
6BR/3BA
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Sleeps 10
– Oak Bluffs #3025276ha
$3250 - $6750 per week
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Waterview, Central Air, Wifi Hi Speed Internet
5BR/3BA
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Sleeps 9
– Oak Bluffs #942453ha
$3400 - $4800 per week
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Bridle Path Beauty , Family Room W/ Pool Table, Large Porch, 47" Lcd H...
3BR/3BA
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Sleeps 8
– Oak Bluffs #942541ha
$1450 - $4200 per week
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Walk to Town and Beach, Newly Renovated
3BR/1BA
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Sleeps 4
– Oak Bluffs #942549ha
$1500 - $1900 per week
- East Chop Water View 5BR/3BA – Sleeps 9 – Oak Bluffs #3221557ha
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East Chop Gem
3BR/2BA
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Sleeps 6
– Oak Bluffs #3240299ha
$1765 - $3175 per week
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In-Town Certified National Historic Oak Bluffs Property -
2BR/1BA
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Sleeps 5
– Oak Bluffs #38273
$125 - $285 per night 2-7 night min stay
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East Chop Oceanview Home with Swimspa/Hot Tub. Lovely!! 4BR+/2BA – Sleeps 8-10 – Oak Bluffs #352115
Special offer Last Minute Cancellations! Great Rate!!!
Jun 21, 2013 to Jul 6, 2013
$929 - $1000 per night 4-7 night min stay -
Beautiful Family Home Short Walk to Oak Bluffs Center
3BR+/2.5BA
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Sleeps 8
– Oak Bluffs #105041
$300 - $371 per night 2-7 night min stay
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Quiet Island Living
1BR+/1BA
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Sleeps 2-3
– Oak Bluffs #34331
$150 - $175 per night 2-7 night min stay
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East Chop 1830 Farmhouse Total Restoration
4BR/2BA
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Sleeps 8
– Oak Bluffs #121097ha
$3200 per week
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Rare Contemporary Oasis
3BR/2BA
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Sleeps 7
– Oak Bluffs #372658
$250 - $283 per night 3 night min stay
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5 Bedroom Victorian in Oak Bluffs
5BR/2BA
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Sleeps 12
– Oak Bluffs #12262
$1750- $3075/wk
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Now Booking Spring & Fall 2013 Weekends and June Vacations!
4BR/3BA
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Sleeps 9
– Oak Bluffs #80321
$2200- $4200/wk
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Classic Vineyard Beach House Near Long Point
5BR/3BA
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Sleeps 10
– Oak Bluffs #114632ha
$133 - $371 per night
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Oak Bluffs Farmhouse, Enclosed Pet Yard, a/C in Bedrooms, Walk to Town
3BR/2BA
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Sleeps 6
– Oak Bluffs #225290ha
$167 - $507 per night
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Immaculate Home-2 Master Suites,Ac,Wifi, Private Day Cruises Avail.
4BR/3BA
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Sleeps 8
– Oak Bluffs #104343
$1800/wk - $2800/wk
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4 Bedroom Martha's Vineyard Retreat - Oak Bluffs
4BR/3BA
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Sleeps 8
– Oak Bluffs #12349
$1850- $2795/wk
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Martha's Vineyard Shipbuilder's Custom Near Beach. Piano/Bikes
3BR/2.5BA
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Sleeps 6
– Oak Bluffs #184127
$1925 per week 7 night min stay
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Pristine in-Ground Pool, Outdoor Hottub, Designer Decorated Family Home.
3BR+/3BA
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Sleeps 7-12
– Oak Bluffs #471186
$600 per night 3 night min stay
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Perfect Location! by Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
2BR/1BA
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Sleeps 4
– Oak Bluffs #3496372ha
$195 - $295 per night 2-7 night min stay
Overview of Oak Bluffs Vacation Rentals
Oak Bluffs Rentals Are Where the Gingerbread Cottages Are Local Landmarks
Just getting to Martha’s Vineyard is an experience. It is an island so forget about bringing the car. Get on the ferry or fly over to Oak Bluffs rentals on this famously beautiful island in the state of Massachusetts. Many Oak Bluffs lodging choices are famously known as "gingerbread cottages" for their bright colors and ornate moldings. The area is known for its vibrant life. These Martha’s Vineyard rentals are perfect for independent travelers seeking lively vacations in this historic and beautiful area.
Oak Bluffs Rentals Let You Ride America’s Oldest Working Carousel
For visitors to Oak Bluffs rentals with children, a not-to-be-missed outing is The Farm Institute, where summer programs teach both children and parents about farming. Also near Oak Bluffs lodging is the Flying Horse Carousel where children can ride the oldest working carousel in the country. Catch the brass ring and get a free ride! A more adult-type trip is the Offshore Ale Company, where a tour of the brewery includes a free sample. These Martha’s Vineyard rentals really do cater to the whole family.
Take to the Air like the Aviators of Yesterday When You Stay in Oak Bluffs Lodging
Want to find out what the glory days of early flight were like? Oak Bluffs rentals are ideally placed so you can head to Classic Aviators, tug on a leather cap and goggles, and head up into the air in an open cockpit aircraft. If you have always wanted to learn to ice skate, head to Martha’s Vineyard Arena and learn a new skill when you vacation at Martha’s Vineyard rentals. Another trip ideal for families who stay in Oak Bluffs lodging is a visit to Island Alpaca to get up close and personal with these wonderfully fascinating animals.
Martha’s Vineyard Rentals Are on Beaches with Calm, Shallow Water
Of course, no visit to the area is complete without several trips to the beach. From Oak Bluffs rentals, you will find a variety of perfect beaches. From the shallow, calm stretches across the eastern side to thundering surf on the south, there is a beach to fit whatever you want from your day. The beaches close to Oak Bluffs lodging are those in the town or at Eastville and Joseph Sylvia State Beach. All these beaches close to Martha’s Vineyard rentals are on the east side and great for those with small children.