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From $1155 per night (USD)
VRBO
Island Inn - Residential Suite - 29G - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Your stay in this charming first-floor corner one and half-bedroom, one and half-bath unit is made comfortable ...
From $1155 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Island Inn - Residential Suite - 39G - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $528 per night (USD)
Expedia
From $782 per night (USD)
VRBO
Island Inn - Studio Suite - 23F - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $782 per night (USD)
VRBO
From $1009 per night (USD)
Expedia
Island Inn - Studio Suite - 5B - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This bright and inviting ground-floor studio suite offers everything you need for a relaxing and rejuvenating ...
From $1009 per night (USD)
Expedia
From $672 per night (USD)
VRBO
Island Inn - Residential Suite - 28G - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Your stay in this charming first-floor corner one and half-bedroom, one and half-bath unit is made comfortable ...
From $672 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Island Inn - Two Bedroom Suite - 1A - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming first-floor corner two-bedroom, one-bath unit is made comfortable with all the esse ...
From $425 per night (USD)
Expedia
From $744 per night (USD)
VRBO
Island Inn - 2 Bedroom & 2 Bath Townhouse - 48G - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor corner two-bedroom, two-bath unit is made comfortable with all the ess ...
From $744 per night (USD)
VRBO
From $1155 per night (USD)
Expedia
Island Inn - Residential Suite - 37G - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $1155 per night (USD)
Expedia
From $712 per night (USD)
VRBO
Island Inn - 2 Bedroom & 2 Bath Townhouse - 50G - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor corner two-bedroom, two-bath unit is made comfortable with all the ess ...
From $712 per night (USD)
VRBO
From $1155 per night (USD)
Expedia
Island Inn - Queen Studio - 24F - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $1155 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Island Inn - King Studio - 27F - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: Your stay in this charming ground-floor, one-bedroom, one-bath unit is made comfortable with all the essential ...
From $316 per night (USD)
VRBO
From $429 per night (USD)
Expedia
Island Inn - Studio Suite - 18D - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming first-floor corner two-bedroom, one-bath unit is made comfortable with all the esse ...
From $429 per night (USD)
Expedia
From $353 per night (USD)
VRBO
Island Inn - Studio Suite - 3B - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This cozy and convenient ground-floor rental offers everything you need for a restful and comfortable stay. Th ...
From $353 per night (USD)
VRBO
From $1009 per night (USD)
Expedia
Island Inn - Studio Suite - 13D - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Step into this inviting suite that offers a perfect blend of comfort and functionality. This unit features two ...
From $1009 per night (USD)
Expedia
From $1009 per night (USD)
VRBO
Island Inn - Residential Suite - 38G - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Summary: Your stay in this charming first-floor one-bedroom, half-wall bedroom, one and half-bath unit is made comforta ...
From $1009 per night (USD)
VRBO
From $948 per night (USD)
Expedia
Island Inn - 2 Bedroom & 2 Bath Townhouse - 47G - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor, two-bedroom, two-bath unit is made comfortable with all the essential ...
From $948 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Island Inn - Studio Suite - 17D - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This unit offers a bright, airy retreat with spacious interiors featuring two comfortable beds adorned with cr ...
From $375 per night (USD)
VRBO
From $1781 per night (USD)
VRBO
Waterview Farm Contemporary Island Home Walk to Beach and Farm Neck Golf Club
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Six bedroom, five and a half bath contemporary island home located in Waterview Farm with direct access to the beach on ...
From $1781 per night (USD)
VRBO
From $3191 per night (USD)
VRBO
Beautiful Oak Bluffs Family Estate
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Perfectly located 1.5 acre beautiful Oak Bluffs getaway across the street from Farm Neck Golf Course and Sengekontacket ...
From $3191 per night (USD)
VRBO
From $458 per night (USD)
VRBO
ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Gorgeous newly renovated and newly furnished mid-century beach cottage designed by prominent interior design firm Tersig ...
From $458 per night (USD)
VRBO
From $547 per night (USD)
VRBO
Cozy, exceptional view, quiet, high speed WIFI, close to all island attractions
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This comfortable house provides up and downstairs amenities. The master bedroom with bath is on the ground floor; the o ...
From $547 per night (USD)
VRBO
From $451 per night (USD)
VRBO
,Artist Guest House on beautiful estate open concept King Sized Bunk Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
quaint quite modern but rustic guest house ideal for couple far from crowds but close to all located in oak bluffs 4 mi ...
From $451 per night (USD)
VRBO
From $1813 per night (USD)
VRBO
SIX BEDROOM COMPOUND W/CENTRAL AIR IN IDYLLIC SETTING
Bedrooms:
3
Bathrooms:
6
Sleeps:
20
Home built 5 years ago with spacious living and open space made just right for family get gatherings. Nine high top ch ...
From $1813 per night (USD)
VRBO
From $1514 per night (USD)
Expedia
Best Kept Secret Retreat for Adults with Water & Golf Course Views!
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Quite, serene, tranquil & beautiful are words guests have used to describe this home. This newly renovated home provide ...
From $1514 per night (USD)
Expedia
From $1292 per night (USD)
VRBO
Picturesque and Private Island Home, Ideal Location for Perfect Island Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Discover the perfect escape from reality in this classic Martha's Vineyard sanctuary. All of this is situated on a 2-ac ...
From $1292 per night (USD)
VRBO
From $340 per night (USD)
VRBO
GREAT PRICE!PETS WELCOME! 2 Decks, Porch,Linens Included,Outdoor Shower, A/C
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
***IMPORTANT--PLEASE "MESSAGE "HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you wi ...
From $340 per night (USD)
VRBO
From $816 per night (USD)
VRBO
FAMILY VACATION- JULY14-21-SLEEP 10, PVT, LONG POINT BEACH
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Certificate #/ Ma. tax: C0221072960 Wonderful, spacious, light and airy home which sits on a private 2 acre prop ...
From $816 per night (USD)
VRBO
From $834 per night (USD)
Expedia
Great Martha's Vineyard House: Everything You Need - Nothing You Don't!
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Property rents Monday to Monday. 3 bedroom/ 2 and 1/2 bathroom Contemporary Vineyard house with wraparound deck, outdoor ...
From $834 per night (USD)
Expedia
From $945 per night (USD)
VRBO
Ellen's MV Hideaway: Down island convenience, solitude, and lots of space!
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
DM me before booking! Ellen’s Hideaway is an impeccably renovated home offering quality, beauty, and comfort, a welcomin ...
From $945 per night (USD)
VRBO
From $814 per night (USD)
VRBO
Beautiful MV Retreat - Central AC - Large Deck, Blue Stone Patio and Fire Pit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Martha's Vineyard! Many of our guests return year after year, drawn by our property’s prime location, cleanli ...
From $814 per night (USD)
VRBO
From $1876 per night (USD)
VRBO
Modern Vineyard Home with Pool, Hot Tub and Pond
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
This is a great home for large families and friends. Amazing amenities include a brand new swimming pool, outdoor shower ...
From $1876 per night (USD)
VRBO
From $1042 per night (USD)
VRBO
Luxurious Sengekontacket Contemporary With Water Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
POINT B EXCLUSIVE - This freshly renovated Luxurious Contemporary combines water views out to Sengekontacket Pond from m ...
From $1042 per night (USD)
VRBO
From $500 per night (USD)
VRBO
Woodsy Home w/Outdoor Living: Deck/Balcony/Patio. Close to Long Pt. & Lambert Cv
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Woodsy, Quiet Home Close to Long Pt Wildlife Ocean & Pond, Lambert's Cove, Towns & Bike Paths* Lots of Outdoor Living: ...
From $500 per night (USD)
VRBO
From $491 per night (USD)
Expedia
Serene Sengekontacket Pond Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The property is set among several private townhouses in a lovely neighborhood located off of Sengekontacket Pond in Oa ...
From $491 per night (USD)
Expedia
From $2949 per night (USD)
VRBO
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $2949 per night (USD)
VRBO
Click For Pricing
Expedia
Access Road to Long Point, Best Island Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a contemporary house, located on over 1 1/2 wooded acres with access to Long Point Beach, considered one of the ...
Click For Pricing
Expedia
From $707 per night (USD)
VRBO
Modern Apt Near Martha's Vineyard Beaches!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Whether you’re embarking on a couple’s weekend retreat or an upscale beach adventure with friends, this Oak Bluff vacati ...
From $707 per night (USD)
VRBO
From $810 per night (USD)
VRBO
Peaceful Summer Oasis
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom 2 bathroom home on a quiet street. The outdoor swing provides a lovely outdoor spaces reading snd relaxing. ...
From $810 per night (USD)
VRBO
From $688 per night (USD)
VRBO
Private island house with close beach access and water view from deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
10
Soundmeadow House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $688 per night (USD)
VRBO
From $779 per night (USD)
Expedia
Breathtaking Waterviews with Private Beach - Harbour House with AC and Heat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Breathtaking views, with a short (2 minute) walk to the private beach and the most prestigious golf course on the island ...
From $779 per night (USD)
Expedia
From $2872 per night (USD)
VRBO
WE’RE BACK! Oak Bluffs Retreat. NEW PRIVATE POOL -- FERRY TIX!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Large beautifully appointed three bedroom, 2 1/2 bath house, with a den perfect for space for everyone to enjoy themselv ...
From $2872 per night (USD)
VRBO
From $882 per night (USD)
VRBO
Completely Renovated Oak Bluffs Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Fully renovated for 2025, this stylish 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis cour ...
From $882 per night (USD)
VRBO
From $584 per night (USD)
VRBO
Charming 2-bedroom townhouse in Oak Bluffs with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Sengekontacket pond in Oak Bluffs is waiting for you at this quiet 2-bedroom townhouse with a private deck overlooking a ...
From $584 per night (USD)
VRBO
From $3919 per night (USD)
VRBO
Brand New Home with Guest House & Heated Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Exquisitely designed new contemporary coastal home, set on a private freshwater pond that connects to a south shore barr ...
From $3919 per night (USD)
VRBO
From $996 per night (USD)
VRBO
Sengekontacket Contemporary With Water Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
**JULY HOT DEAL: SAVE 10% OFF 7/13 - 7/20 OR SHORTER STAY AVAILABLE | BOOK BY PHONE** POINT B EXCLUSIVE - Tucked away in ...
From $996 per night (USD)
VRBO
From $1338 per night (USD)
Expedia
Enchanting home with tennis, firepit, golf nearby & washer/dryer
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Bird's Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $1338 per night (USD)
Expedia
From $3755 per night (USD)
VRBO
Main house and a separate apartment with saltwater pool, spa, outdoor cooking!
Bedrooms:
6
Bathrooms:
7
Sleeps:
12
Forget your worries in this spacious and serene space. Tucked away, the brand new compound offers all amenities. Heated, ...
From $3755 per night (USD)
VRBO
From $3252 per night (USD)
VRBO
Luxury home with pool in tranquil West Tisbury setting
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Fabulous luxury contemporary coastal home. The property is beautifully landscaped and perfectly situated with views of ...
From $3252 per night (USD)
VRBO
From $681 per night (USD)
VRBO
MODERN BEACH COTTAGE IN PRIVATE WATERFRONT COMMUNITY ON SENGEKONTACKET Pond
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FIRST TIME OFFERED...This bright and airy beach cottage is newly renovated and furnished (2021), primarily for our perso ...
From $681 per night (USD)
VRBO
From $6933 per night (USD)
Expedia
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Our amazing property is a perfect place to spend with family and friends! The property is wonderful for everything from ...
From $6933 per night (USD)
Expedia
From $2931 per night (USD)
VRBO
BEAUTIFUL CUSTOM BUILT HOUSE WITH A POOL AND HOT TUB!!!
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
A gorgeous builder's house; this hidden pearl is elegant, private and relaxing. Conveniently located 3 miles from the Tr ...
From $2931 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Lovely two bedroom apartment with indoor fireplace
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
It’s very cozy and comfortable, New Construction, if you like to do walk is close to the path and trial, ride bikes, it ...
From $495 per night (USD)
Expedia
Click For Pricing
VRBO
Updated home with forest views, deck, firepit, fast WiFi - near town/beaches
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
White Pearl Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
VRBO
From $546 per night (USD)
Expedia
Modern Family Home Walkable to Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unwind at this stunning newly renovated home with modern furnishing! The home is on a quiet, well-maintained private roa ...
From $546 per night (USD)
Expedia
From $590 per night (USD)
VRBO
Martha's Vineyard. Spacious Living Inside & Out! Sleeps 8!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your entire group will love this large centrally located private home that offers easy access to everything on The Viney ...
From $590 per night (USD)
VRBO
From $1166 per night (USD)
VRBO
Hidden Dream MV Getaway
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: Forget your worries in this spacious and serene space. Our beautiful family home is located Up Island and makes ...
From $1166 per night (USD)
VRBO
From $2896 per night (USD)
VRBO
Brand New 5 Bedroom Compound With Pool and Guest House!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Brand new secluded waterfront getaway on one of Martha's Vineyards most desirable ponds! This 5.5-acre property enjoys o ...
From $2896 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Carriage House, Swimming, Boating, Kayaking, just steps from your door...
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
WELCOME TO PARADISE!!! we sanitize!!!!! We have implemented a system so you are able to check in and out without and per ...
From $419 per night (USD)
VRBO
From $562 per night (USD)
VRBO
Beautiful Landscaped Grounds and Pond & Kayaks
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to paradise!!! This beautiful property is located in prestigious fresh pond estates. It sits tucked away in the ...
From $562 per night (USD)
VRBO
From $484 per night (USD)
VRBO
Spectacular Martha's Vineyard Island Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
This is our beautiful home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overl ...
From $484 per night (USD)
VRBO

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