Lakeside Park, Massachusetts Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Lakeside Park, Massachusetts on RentalSaver.com!

Lakeside Park Rentals

From $778 per night (USD)
VRBO
Elegant Dream Home w/ Luxurious Living Spaces, Full Kitchen, & Wraparound Porch
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Oak Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $778 per night (USD)
VRBO
From $1316 per night (USD)
VRBO
Welcome to The “SUMMER WIND” House! 5-Minutes to the Beach!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
THE “SUMMER WIND” HOUSE - WALK TO EVERYTHING! We have completely renovated our 5-bedroom, 3-full bathroom home with cent ...
From $1316 per night (USD)
VRBO
From $672 per night (USD)
VRBO
CHARMING HISTORIC ISLAND HOME--WEEKLY RENTAL-- OAK BLUFFS
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Welcome to "Eventide." Your historic vacation home is nestled at 63 Temahigan Ave. in Oak Bluffs- Martha's Vineyard. Con ...
From $672 per night (USD)
VRBO
From $1145 per night (USD)
Expedia
Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Renovated in 2022, The Panola House is tucked away on a private lot with its own roundabout driveway. Walk to the cente ...
From $1145 per night (USD)
Expedia
From $338 per night (USD)
VRBO
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Bedrooms:
0
Bathrooms:
3
Sleeps:
6
Family owned and kept charming 19th century home in Oak Bluffs highlands near Baptist Temple park. This house is about ...
From $338 per night (USD)
VRBO
From $575 per night (USD)
Expedia
Family & dog friendly; walk to beach, cliff, town, ferries, all bedrooms w/AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Best of both worlds! Quietly situated among beautiful trees with few neighbors plus it is walking distance to swim and O ...
From $575 per night (USD)
Expedia
From $684 per night (USD)
VRBO
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation ...
From $684 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Cozy cottage 3/4 mile from Oak Bluffs harbor
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Family owned/charming home in Oak Bluffs, 1/2 mile walk to East Chop Lighthouse and slightly more to the town harbor, wh ...
From $329 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Lakefront Cottage with a Deck, Free WiFi, Gas Grill - Close to Ferries & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Sunset Meadows Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $424 per night (USD)
VRBO
From $692 per night (USD)
Expedia
Historic Home with Gorgeous Antiques & Mondern Conveniences
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Samoset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $692 per night (USD)
Expedia
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VRBO
Charming, Dog-Friendly House with Lots of Entertainment & Gourmet Kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bright Grove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
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VRBO
From $1065 per night (USD)
Expedia
New Construction with Patio & Yard - Downtown & Beaches
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Oak Bluffs Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1065 per night (USD)
Expedia
From $371 per night (USD)
VRBO
Martha's Vineyard Apt ~ 1 Mile to Inkwell Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience the charm of Martha’s Vineyard at your leisure from this ideally located apartment. With 2 bedrooms and 1 bat ...
From $371 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Quaint,,,Quiet..up island feel yet a short walk to town and harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Your quintessential summer vacation starts here! The property has a combination of a strong rental history(read ren ...
From $383 per night (USD)
Expedia
From $766 per night (USD)
VRBO
Beautiful downtown Oak Bluffs!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Beautifully decorated ranch style home in Oak Bluffs Center. Close to the beach, restaurants, shopping, parks, library a ...
From $766 per night (USD)
VRBO
From $699 per night (USD)
Expedia
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity, ...
From $699 per night (USD)
Expedia
From $750 per night (USD)
VRBO
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This property is conveniently located near the center of Oak Bluffs and with many great restaurant and out door activity ...
From $750 per night (USD)
VRBO
From $533 per night (USD)
Expedia
Charming MV Cottage: Walk to Dtwn Oak Bluffs!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
There's no better way to experience the laidback lifestyle of the Vineyard than in the heart of it all at this tradition ...
From $533 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Peaceful Oak Bluffs home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax and pamper yourself kin a Mid-Century Modern Split-Level home. Located on a 1/4 acre lot minutes away from town,b ...
From $479 per night (USD)
VRBO
From $651 per night (USD)
Expedia
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Introducing our #CozyBluffs home in Oak Bluffs on Martha's Vineyard! Designed by local Architect Chuck Sullivan and buil ...
From $651 per night (USD)
Expedia
From $680 per night (USD)
VRBO
Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Oak Leaf Cape Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $680 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Island Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $396 per night (USD)
Expedia
From $1709 per night (USD)
VRBO
Island bliss located near shops and eateries-several island beaches also nearby
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Island Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1709 per night (USD)
VRBO
From $1400 per night (USD)
Expedia
Beautiful 5 BR, 4.5 baths w/ modern conveniences
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
We welcome you to enjoy our spacious and comfortable home. It's a beautiful 5 BR, 4.5 bath Oak Bluffs home with modern ...
From $1400 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Bright old-world cottage with two porches & large yard - walk to town & beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oak Bluffs Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $561 per night (USD)
VRBO
From $1229 per night (USD)
Expedia
Classic Vineyard Ocean, Harbor, Lake & Parkview Cottage w/AC
Bedrooms:
2
Bathrooms:
7
Sleeps:
10
The cottage is in restored original condition with many original features including hardwood floors, paned windows with ...
From $1229 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Cute & cozy cottage with a patio & gas grill in the heart of Martha's Vineyard
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Winthrop Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $392 per night (USD)
VRBO
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Expedia
Historic Beach Front Victorian Home
Bedrooms:
4
Bathrooms:
9
Sleeps:
20
This home is sure to bring you and your family and/or friends an unforgettable vacation. Begin the day with unobstructed ...
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Expedia
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VRBO
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This lovely, spacious, and beautifully appointed condo is just steps from the beach and a short walk to the heart of Oak ...
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VRBO
From $797 per night (USD)
Expedia
Oak Bluffs - Quiet Neighborhood - Walk to Town, Ferry, Library and more!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This property is situated in a quiet neighborhood just a short walk to downtown Oak Bluffs. This location is perfect. ...
From $797 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Cozy Beach Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Newly refurbished Cottage City Victorian beach house, built in 1870. Walk to beach, walk to town. 2 bedrooms up a narro ...
From $307 per night (USD)
VRBO
From $1504 per night (USD)
Expedia
Akwaaba House Martha's Vineyard Walk to Beach and Oak Bluffs Town & Harbor
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Newly renovated, Great for Family & Friend Stays, Corporate Retreats, Central Air & Heat, walk to Circuit Ave and Beach, ...
From $1504 per night (USD)
Expedia
From $657 per night (USD)
VRBO
Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch.
Bedrooms:
2
Bathrooms:
6
Sleeps:
13
*** CONTACT THE HOST TO CONFIRM DATES BEFORE INSTANT BOOKING. VRBO FEES ARE NON-REFUNDABLE *** *** CONTACT THE HOST FOR ...
From $657 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Beautiful 3 bedroom 2 bath Home / Close to Town & Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful and spacious 3 bedroom and 2 bathroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape style home. ...
From $413 per night (USD)
Expedia
From $635 per night (USD)
VRBO
Serene home with backyard barbecue area - bike to Arts District, 1 mile to beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Vineyard Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $635 per night (USD)
VRBO
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Expedia
Enjoy a Martha’s Vineyard vacation in this clean and beautiful apartment!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautifully updated apartment is located minutes from Oak Bluffs beaches, shopping and restaurants. Enjoy meals in the ...
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Expedia
From $973 per night (USD)
VRBO
Beautiful Carriage House on the Chop
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Recently built, this spectacular 3 Bedroom carriage house is located on 3/4 acre estate on beautiful East Chop Drive. Th ...
From $973 per night (USD)
VRBO
From $539 per night (USD)
Expedia
Wonderful three-story home with lovely decks, firepit, fast WiFi & washer/dryer
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Brewster House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $539 per night (USD)
Expedia
From $577 per night (USD)
VRBO
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
This home has all the amenities to make your stay a comfortable one. Its character stems from being built in the 1920s w ...
From $577 per night (USD)
VRBO
From $971 per night (USD)
Expedia
Newly remodeled home w/ new furniture, large yard & great porches
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Sunny Side Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $971 per night (USD)
Expedia
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VRBO
Traditional Martha's Vineyard Home w/ Porch & Yard
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This exquisite, shingled Colonial house with an expansive wraparound porch is synonymous with Martha's Vineyard architec ...
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VRBO
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Expedia
Quaint and pristine home with private suites and baths.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to our home! We are a husband & wife interior decorator/contractor team, who've tastefully renovated our entire ...
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Expedia
From $543 per night (USD)
VRBO
1 Bedroom, Sleeps 4; perfect small family vacation home
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Close to town and beach, but far enough away for peaceful quiet. 1 Bedroom; 3.5 bath; outdoor shower; front and side por ...
From $543 per night (USD)
VRBO
$Welcome to \Suzy's Place\ Best Location! Walk Everywhere. Newly built in 2024.$
From $670 per night (USD)
VRBO
Welcome to \"Suzy's Place\" Best Location! Walk Everywhere. Newly built in 2024.
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
"Suzy's Place" is arguably the best location on the island. Your cozy getaway awaits in Oak Bluffs at this beautiful new ...
From $670 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Updated house close to town and beach with patio, AC, and games
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Sankofa House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $606 per night (USD)
VRBO
From $458 per night (USD)
Expedia
BRAND NEW 1-bedroom Owner's Suite in wonderful Oak Bluffs with Air Conditioning
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Get ready to relax in this 1-bedroom Owner's Suite in Oak Bluffs. This brand new property features a cozy bedroom with a ...
From $458 per night (USD)
Expedia
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VRBO
Oak Bluffs Spacious 4-Bedroom Rental – Private Entrance & Newly Renovated Deck!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Spacious 4-Bedroom Rental in Oak Bluffs – Private Entrance & Newly Renovated Deck! Enjoy the best of Oak Bluffs in this ...
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VRBO
From $703 per night (USD)
Expedia
Steps to Inkwell Beach: Victorian Home!
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
2,150 Sq Ft | Family Friendly | Walk to Shops, Restaurants, Ferry Terminal | Outdoor Shower & Grill It doesn't get any ...
From $703 per night (USD)
Expedia
From $490 per night (USD)
VRBO
NEWLY RENOVATED! Quiet location, walk to Circuit Avenue and beaches!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Your home away from home in Oak Bluffs with 4 bedrooms, including a ground floor bedroom and bath with zero-entry shower ...
From $490 per night (USD)
VRBO
From $1009 per night (USD)
Expedia
Island Inn - One Bedroom Suite - 10C - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: This suite is a charming and cozy retreat, ideal for a relaxing getaway. It features a comfortable queen bed, ...
From $1009 per night (USD)
Expedia
From $1009 per night (USD)
VRBO
Island Inn - Two Bedroom Suite - 2A - Dog-freindly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: This charming first-floor one-bedroom retreat, featuring a queen bed, offers the quintessential Martha’s Viney ...
From $1009 per night (USD)
VRBO
From $789 per night (USD)
Expedia
Island Inn - Queen Studio - 22F - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Your stay in this charming ground-floor corner one-bedroom, one-bath unit is made comfortable with all the ess ...
From $789 per night (USD)
Expedia
From $1009 per night (USD)
VRBO
Island Inn - Studio Suite - 7C - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This ground-floor studio unit offers a charming and practical retreat on Martha's Vineyard. The exterior featu ...
From $1009 per night (USD)
VRBO
From $1009 per night (USD)
Expedia
Island Inn - Studio Suite - 12D - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: This suite is a cozy, functional accommodation featuring a cheerful and bright ambiance with its light blue wa ...
From $1009 per night (USD)
Expedia
From $1082 per night (USD)
VRBO
Island Inn - 2 Bedroom & 1.5 Bath Townhouse - 43G - Dog-friendly - Oak Bluffs, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming second-floor corner two-bedroom, one and half-bath unit is made comfortable with al ...
From $1082 per night (USD)
VRBO
From $1155 per night (USD)
Expedia
Island Inn - Cottage - 21E - Oak Bluffs, MA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Your stay in this charming first-floor corner two-bedroom, each with a Queen Bed, an additional full Sofa-bed ...
From $1155 per night (USD)
Expedia
From $977 per night (USD)
VRBO
Victorian cottage overlooking downtown Oak Bluffs and the Harbor.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Come stay at our quaint Victorian cottage overlooking downtown Oak Bluffs and the Harbor, which are just a few blocks aw ...
From $977 per night (USD)
VRBO
From $905 per night (USD)
VRBO
Charming 3BR Vineyard Retreat, Lg Deck w/ Kitchen, Near Beach, Town Ctr & Ferry
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to RoBree Farm – Your Martha’s Vineyard Retreat in the Heart of Oak Bluffs Escape to the serenity and magic of ...
From $905 per night (USD)
VRBO
From $963 per night (USD)
VRBO
Charming home with walkable beach, large yard, deck, fire pit, and A/C
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $963 per night (USD)
VRBO
From $1006 per night (USD)
VRBO
EXQUISITE MARTHA'S VINEYARD HOME, HEATED POOL, 10 MIN WALK TO OAK BLUFFS FERRY
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with v ...
From $1006 per night (USD)
VRBO
From $1078 per night (USD)
VRBO
Designer Stay- Large Yard- Outdoor games
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
A chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just ...
From $1078 per night (USD)
VRBO
From $1056 per night (USD)
VRBO
Updated 3-bedroom in gorgeous Oak Bluffs w/ waterviews and expansive front porch
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Get ready to relax in this 3-bedroom cottage in Oak Bluffs. Nestled in a peaceful neighborhood, this beautiful property ...
From $1056 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Martha’s Vineyard 15 minute walk to Oak Bluffs Beach and Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
15 minute walk to Oak Bluffs town and beach. 2 queen beds. 5 minute walk to the bus. 5 minute walk to library. 1 bedroom ...
From $465 per night (USD)
VRBO
From $1617 per night (USD)
VRBO
Cozy Oak Bluffs Cottage walk to town Pet Friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This modest single-family home was newly renovated in 2023. It is a single-level house just west of downtown Oak Bluffs. ...
From $1617 per night (USD)
VRBO
From $927 per night (USD)
VRBO
Beautiful and Modern 4Bdrm, 3Ba Colonial w/ a Large Yard in Historic Oak Bluffs!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Gloria’s Cottage – A Martha’s Vineyard Retreat Step into the warmth of Gloria’s Cottage, a beautifully appoi ...
From $927 per night (USD)
VRBO
From $541 per night (USD)
VRBO
Cottage located in Heart of Oak Bluffs is open for booking the week of 8/9-8/16
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away ...
From $541 per night (USD)
VRBO
From $1228 per night (USD)
VRBO
4 BR/4 BA Modern Victorian: The Mack on Winemack
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This beautiful Victorian home has all the charm of a true Martha’s Vineyard Gingerbread cottage combined with all of the ...
From $1228 per night (USD)
VRBO
From $1446 per night (USD)
VRBO
Oceanfront Home - Walk to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Endless water views, fully updated, and steps from a sandy beach excellent for swimming ("Inkwell"/Oak Bluffs Town Beach ...
From $1446 per night (USD)
VRBO
From $1110 per night (USD)
VRBO
Newly Renovated! Walk to Town Oak Bluffs, 4 Bedroom/3 Bath A/C
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This newly renovated home is approximately 2100sf with 4 bedrooms and 3 bathrooms. Furnished and decorated by award winn ...
From $1110 per night (USD)
VRBO
From $369 per night (USD)
VRBO
Downtown Oak Bluffs, short walk to beach & town
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Location, location, location. This cozy 3 bedroom house is located steps from downtown on a family neighborhood side str ...
From $369 per night (USD)
VRBO
From $783 per night (USD)
VRBO
Spacious Home - 1500 ft from Beach & Circuit Ave
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Newly renovated four bedroom, two full bathroom home with an inviting front porch, private backyard and footsteps to Ci ...
From $783 per night (USD)
VRBO
From $622 per night (USD)
Expedia
Within Walking Distance to Town, Beach & Parks, Enclosed yard with a new deck,
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Located on historic Circuit Ave in Oak Bluffs within walking distance to town, beach, tennis courts and parks. Minutes a ...
From $622 per night (USD)
Expedia
From $642 per night (USD)
VRBO
Great location, happy house 0.5 mile Nancy’s & Jetty Beach.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
1900's Victorian, renovated and newly furnished. House is located on New York Ave, which is the main road between Oak Bl ...
From $642 per night (USD)
VRBO
From $552 per night (USD)
VRBO
Adorable Oak Bluffs Cottage With Ac On East Chop
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Adorable 4 bedroom cottage in the East Chop neighborhood of Oak Bluffs. You will love the beautiful back yard that has a ...
From $552 per night (USD)
VRBO
From $926 per night (USD)
VRBO
Beach, Town, Tennis, Pickleball - Central AC
Bedrooms:
2
Bathrooms:
6
Sleeps:
15
We will let the photos do the talking, but note that this home has some especially attractive features for large groups, ...
From $926 per night (USD)
VRBO
$Your \Vineyard Dream\ Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town$
From $453 per night (USD)
VRBO
Your \"Vineyard Dream\" Vacation - OAK BLUFFS -Sunny Open Floor Plan Close to Town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A BEAUTIFUL PROPERTY CLOSE TO TOWN-GREAT PRICE! LOTS OF PRIVACY BUT CLOSE TO EVERYTHING IN OB. ONE WEEK MINIMUM FOR ALL ...
From $453 per night (USD)
VRBO
From $320 per night (USD)
VRBO
The Sweetest Suite – Beach, kayaks & Starry Nights
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your perfect island escape. Tucked beneath a canopy of soaring 70-foot trees, our charming guest suite offers ...
From $320 per night (USD)
VRBO
From $410 per night (USD)
VRBO
The Nest, Comfortable, Cozy and Convenient
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Nest is a private entranced guesthouse that is ideally located 2/3-1 mile walking distance to Oak Bluffs town, har ...
From $410 per night (USD)
VRBO
From $795 per night (USD)
VRBO
Beach and downtown OB walkable! 5 Bedroom Victorian on the park.
Bedrooms:
1
Bathrooms:
5
Sleeps:
11
You will find this 5 Bedroom Victorian quite charming with its bright & cheery interior. Located right across from wide ...
From $795 per night (USD)
VRBO
From $831 per night (USD)
VRBO
OAK BLUFFS - INKWELL WATERVIEW Renovated Cottage with A/C, modern decor
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautifully renovated in-town Victorian Cottage. 4 bedrooms and 2.5 baths. 2 of the 4 bedrooms with a partial water view ...
From $831 per night (USD)
VRBO
From $973 per night (USD)
VRBO
The Island Collection MV: Experience a Luxury Getaway by the Lagoon
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful 3 bedroom home is located in a quiet area on Martha’s Vineyard by Lagoon Pond. When you walk inside, you ...
From $973 per night (USD)
VRBO
From $987 per night (USD)
VRBO
PRIVATE WATER ACCESS! ON FARM NECK GOLF COURSE! Kayaks & Canoe & A/C
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Immaculately clean, beautifully furnished three bedroom, 2 and 1/2 bath beach house in private community. Community is ...
From $987 per night (USD)
VRBO
From $847 per night (USD)
VRBO
Magnificent Spacious Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This lovely and beautifully furnished three-story home is located in a quiet residential section of Oak Bluffs. It is a ...
From $847 per night (USD)
VRBO
From $709 per night (USD)
VRBO
Beautiful home with pool in great location- close to everything!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom home with 2 big full bathrooms. Walk to ferry and town center. One of the bathrooms include a jacuzzi tub and ...
From $709 per night (USD)
VRBO
From $1368 per night (USD)
VRBO
Coastal Farmhouse With Connected Carriage House
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
**JULY HOT DEALS: SAVE 10% OFF 7/12 - 7/19; 7/19 - 7/27 | AVAILABLE BY PHONE ONLY** POINT B EXCLUSIVE - This newly built ...
From $1368 per night (USD)
VRBO
From $1022 per night (USD)
VRBO
Modern Farmhouse In Central Oak Bluffs Neighborhood
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
**JULY HOT DEALS: SAVE 10% OFF WEEKLY RENTALS 7/14 - 7/26 OR SHORTER STAYS ALSO AVAILABLE | BOOK BY PHONE ONLY** POINT B ...
From $1022 per night (USD)
VRBO
From $957 per night (USD)
VRBO
Spacious Victorian, 5 minute walk to beach, town, and ferry in Oak Bluffs
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Welcome to the Oak Bluffs Victorian Cottage that dreams are made of! Newly renovated (summer 2017), the rambling Main H ...
From $957 per night (USD)
VRBO
From $347 per night (USD)
VRBO
Please let us know in advance which ferry you’re on and arrival time.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Fully equipped cottage behind the main house, Private, available all year round! Perfect romantic get away. Back Patio ...
From $347 per night (USD)
VRBO
From $1945 per night (USD)
VRBO
The Island Collection MV: 10% Price drop in July weeks 7/12-7/19 and 7/26-8/2
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Enjoy a relaxing ferry ride to Oak Bluffs and its picturesque surroundings. Once your ferry ride ends, you’re steps away ...
From $1945 per night (USD)
VRBO
From $471 per night (USD)
Expedia
Charming Studio Guest House in the Heart of Oak Bluffs
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This recently renovated charming studio guest house in the heart of Oak Bluffs sleeps 2 in a Queen size bed. Complete w ...
From $471 per night (USD)
Expedia
From $1023 per night (USD)
VRBO
Perfect Autumn Getaway! OAK BLUFFS 5 Bedroom/3 Bath/Central AC.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This is one summer school you won't want to miss! Bright, airy, elegant home is perfect combination of past and present ...
From $1023 per night (USD)
VRBO
From $662 per night (USD)
VRBO
Island Serenity: Beautiful home in quiet neighborhood close to Oak Bluffs
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lovely 3 bedroom, 2 full bathroom home with huge deck is less than 1 mile walk to famous Circuit Avenue in Oak Bluffs an ...
From $662 per night (USD)
VRBO
From $1411 per night (USD)
VRBO
Home in Oak Bluffs near everything you want! Walk to Inkwell Beach in 7 min.
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Surround yourself with comfort and fresh furnishings! This is a beautiful four-year-old home that is stylishly furnishe ...
From $1411 per night (USD)
VRBO
From $335 per night (USD)
VRBO
Sweet Little Post&Beam
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Very comfortable well appointed 750 sq ft home with heat and AC. Has 1 bedroom upstairs with a queen size bed and a hal ...
From $335 per night (USD)
VRBO
From $593 per night (USD)
VRBO
Charming Gingerbread Cottage in Historic Campgrounds in Oak Bluffs Sleeps Nine
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Extra-large gingerbread cottage in historic Campgrounds in Oak Bluffs, sleeps nine. Located on a double lot in the hear ...
From $593 per night (USD)
VRBO
From $2545 per night (USD)
VRBO
East Chop Beach House w/Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Fabulous new house in East Chop completed in 2019 located in the heart of East Chop. The house is well appointed, very ...
From $2545 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If Steamship Authority ferry reservations appear to be unavailable, please contact me for possible options. Please not ...
From $528 per night (USD)
VRBO
From $1201 per night (USD)
Expedia
Original Pratt House built in 1866 with Ocean View of the Inkwell beach.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This is an original Pratt house built in 1866 by the famed architect Pratt for whom the Pratt Institute in New York was ...
From $1201 per night (USD)
Expedia
From $251 per night (USD)
VRBO
Martha's Vineyard Oak Bluffs East Chop Summer Vacation Rental Home 4 Bedroom
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Tucked in a quiet neighborhood and within walking distance to town and beaches, this quaint cottage was moved to East Ch ...
From $251 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Conveniently located near Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This comfortable home has all the amenities of home in an idyllic setting, easy access to town, beach and gorgeous East ...
From $423 per night (USD)
Expedia

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