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/3.5BA – Sleeps 12 – Oak Bluffs #133568ha
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Charming East Chop Home, Quiet, Walk/Bike to Town, Awesome Water Views!
4BR/2BA
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Sleeps 6
– Oak Bluffs #227256ha
$371 - $557 per night
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Luxury Loft Historic Center Oak Bluffs
5BR+/2.5BA
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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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Beautiful Home Close to Beach and Town
3BR/2BA
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Sleeps 6
– Oak Bluffs #235942
$214 - $310 per night
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Walk to Beach, Town and Park from Gorgeous Martha's Vineyard Home
6BR/2.5BA
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Sleeps 10
– Oak Bluffs #221408
$171 - $743 per night
- Breathtaking Waterviews with Private Beach - Harbour House 4BR/2.5BA – 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 – Sleeps 12-14 – Oak Bluffs #271261
Special offer June Special - Save $100s
Jun 9, 2013 to Jun 16, 2013
$3,000- $13,000/wk -
Modern Design Home W/ Private Beach Access.Spacious,Chic,Open,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/2.5BA
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Sleeps 15
– Oak Bluffs #43151
$1500- $5250/wk
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Lovely 3 Bedrm, 3 Bath Home W/Ac;Steps to Lagoon & Walk to Town
3BR+/3.5BA
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Sleeps 6
– Oak Bluffs #343277
$1,500- $3,000/wk; $550.00/nt min 3 nt
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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
$800 - $829 per night
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Sept Availability! East Chop, Quiet, Walk/Bike to Town, Awesome Views!
4BR/2.25BA
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Sleeps 6
– Oak Bluffs #313472
$2600- $3900/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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Sunny Large House, Quiet Street, Short Walk to Town and Beaches
4BR/2.5+BA
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Sleeps 8
– Oak Bluffs #252977ha
$143 - $557 per night
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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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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/4.5BA
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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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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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2013 Fall Getaways - Now Booking!
4BR/2BA
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Sleeps 8
– Oak Bluffs #413958
$900- $3400
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Luxury Home with Water Views in Farm Neck! Ob523
5BR/4.5BA
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Sleeps 8
– Oak Bluffs #3250419ha
$1071 - $1557 per night
- Chickawaukee Two 2BR/1.5BA – Sleeps 4 – Oak Bluffs #3221391ha
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Just Opened up Fireworks Weekend, August 15-18. Great Location. Ac, New Home 4BR+/3BA – Sleeps 9 – Oak Bluffs #342749
Special offer $75 off per night
Jun 23, 2013 to Jun 30, 2013
$350 - $625 per night 2-7 night min stay -
Contemporary Luxury Open-Air Loft in the Heart of the Arts District
3BR/3BA
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Sleeps 6
– Oak Bluffs #242039
$286 - $536 per night
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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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Location, Location, Location!
4BR+/2BA
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Sleeps 8
– Oak Bluffs #59668
$900- $2900/wk
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Hilltop Waterview Home, 5BR with Universal (Handicap) Access
5BR+/3.5BA
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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+/1BA
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Sleeps 10-12
– Oak Bluffs #3508963ha
$7800 per week 7 night min stay
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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+/3.5BA
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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
$314 - $471 per night
- 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
$436 per night
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Private Beach Access in Great Neighborhood
3BR/2.5BA
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Sleeps 6
– Oak Bluffs #249612
$2000 - $2800 per week 7 night min stay
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Just 2 Summer Weeks Left or Come for the Beautiful Off Season
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/1.5BA
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Sleeps 10
– Oak Bluffs #105316ha
$300 - $557 per night
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Spectacular Waterviews, Private Waterfront, Oceanview Villa
3BR/2BA
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Sleeps 6
– Oak Bluffs #164102
$257 - $371 per night
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Dreamy Waterfront Beach Cottage in East Chop on Mv
3BR+/1.5BA
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Sleeps 6-7
– Oak Bluffs #107969
4000- 5000
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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
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Sleeps 6
– Oak Bluffs #124998
$1700- $2775 per week
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Exquisite East Chop Waterview Home/Swimspa Labor Day Week Available!
6BR+/4.5BA
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Sleeps 15
– Oak Bluffs #338384
$8505 per week 7 night min stay
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Executive Oceanview Hilltop Home with Spectacular Sunrises.
4BR+/4.5BA
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Sleeps 8-10
– Oak Bluffs #361199
$857 - $1000 per night 2-7 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
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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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Great Family 6 Bedroom House on the Hill Overlooking Oak Bluff Harbor
6BR+/2.5BA
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Sleeps 9-10
– Oak Bluffs #301726
$3200- $4700/wk
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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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Gingerbread Cottage - Harbor View
5BR+/1.5BA
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Sleeps 11-12
– Oak Bluffs #349343
$2700 per week 7 night min stay
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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/wk to $2100/wk + $100 cleanng fee
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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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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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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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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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Sweet Little Space
2BR/2BA
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Sleeps 4
– Oak Bluffs #236250
$1500- $1850/wk
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Impeccable East Chop Cottage
2BR+/1.5BA
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Sleeps 5
– Oak Bluffs #356558
$1400- $2200/wk
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Charming Island House-Close to Ginger Bread Cottages, Beaches, Shops.. 3BR/2BA – Sleeps 8 – Oak Bluffs #937169ha
Special offer 20% of June and September bookings!
Jun 17, 2013 to Sep 8, 2013
$214 - $357 per night -
Lagoon Pond
3BR/2BA
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Sleeps 4-6
– Oak Bluffs #451916
$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 – Sleeps 6-7 – Oak Bluffs #462367
Special offer EXTRA DAY for weeklong rentals!
Jul 7, 2013 to Aug 3, 2013
$1200- $3000/wk -
Waterfront Home in Oak Bluffs – Walk to Town and Beach 4BR+/1.5BA – Sleeps 8 – Oak Bluffs #401921
Special offer $500 discount for July 4th week!
Jun 29, 2013 to Jul 6, 2013
June $4000, July $4500-5000, Aug $5000 -
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 in-Town Rental, Cinderella Cottage! Ob503
4BR/2.5BA
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Sleeps 8
– Oak Bluffs #3198075ha
$443 - $757 per night
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Oak Bluffs Rental, Tranquil Neighborhood Ob502
3BR/2.5BA
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Sleeps 6
– Oak Bluffs #3198073ha
$214 - $257 per night
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Oceanfront Cottage on Nantucket Sound! Ob529
2BR/1BA
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Sleeps 6
– Oak Bluffs #3198107ha
$982 per night
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Waterview Seaview Condos #203! Ob518
2BR/2BA
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Sleeps 4
– Oak Bluffs #3198097ha
$329 - $400 per night
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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
$329 - $400 per night
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Waterview Seaview Condo #304- Ob517
2BR/2BA
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Sleeps 4
– Oak Bluffs #3198095ha
$329 - $400 per night
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1611 - 2012 Colonial Renovation in Oak Bluffs
5BR/3.5BA
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Sleeps 13
– Oak Bluffs #3019695ha
$357 - $693 per night
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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
$329 - $500 per night
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East Chop, Waterfront, Wifi Internet
5BR/5BA
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Sleeps 9
– Oak Bluffs #942452ha
$900 - $1114 per night
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Waterview, Central Air, Wifi Hi Speed Internet
5BR/3.5BA
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Sleeps 9
– Oak Bluffs #942453ha
$486 - $686 per night
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Classic East Chop Summer Home, Wifi Internet
6BR/4BA
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Sleeps 10
– Oak Bluffs #942466ha
$457 - $600 per night
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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
$207 - $600 per night
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East Chop - Walk to Town, Wifi, Central a/C
5BR/2BA
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Sleeps 8
– Oak Bluffs #942594ha
$436 - $707 per night
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Walk to Town and Beach, Newly Renovated
3BR/1BA
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Sleeps 4
– Oak Bluffs #942549ha
$214 - $271 per night
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Gorgeous Ocean View Cottage Home, Ink Well Beach Across Street, Walk T...
6BR/3.5BA
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Sleeps 10
– Oak Bluffs #3025276ha
$464 - $964 per night
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651-Lovely Home Centrally Located to Town & Beach
3BR+/1BA
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Sleeps 8
– Oak Bluffs #3019365ha
$407 - $493 per night
- The Tucker Inn 9BR/6BA – Sleeps 21 – Oak Bluffs #3221626ha
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Owner Says, 'Raise Cash. Reduce Rates by 20%
3BR/2BA
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Sleeps 8
– Oak Bluffs #3236729ha
$150 - $225 per night 3-7 night min stay
- East Chop Water View 5BR/3.5BA – Sleeps 9 – Oak Bluffs #3221557ha
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East Chop Gem
3BR/2.5BA
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Sleeps 6
– Oak Bluffs #3240299ha
$252 - $454 per night
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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 1830 Farmhouse Total Restoration
4BR/2BA
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Sleeps 8
– Oak Bluffs #121097ha
$457 per night
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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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Classic Vineyard Beach House Near Long Point
5BR/3BA
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Sleeps 10
– Oak Bluffs #114632ha
$133 - $500 per night
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East Chop Oceanview July Availability! Book Now!
4BR+/2.5BA
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Sleeps 8-10
– Oak Bluffs #352115
$929 - $1000 per night 4-7 night min stay
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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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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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5 Bedroom Victorian in Oak Bluffs
5BR/2BA
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Sleeps 12
– Oak Bluffs #12262
$1750- $3075/wk
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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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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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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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Look No Further.. Classic Cape, End of Road, Walk to Town
4BR+/2.5BA
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Sleeps 11-14
– Oak Bluffs #59620
$1900- $2900/wk (discounts apply)
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.