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 $523 per night (USD)
VRBO
Beautiful Contemporary Farmhouse close to Oak Bluffs
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Beautifully maintained contemporary farmhouse features an open floor plan. The first floor has an open kitchen, dining, ...
From $523 per night (USD)
VRBO
From $1090 per night (USD)
VRBO
Big Beach House - Ocean Views!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. ...
From $1090 per night (USD)
VRBO
From $424 per night (USD)
VRBO
Martha's Vineyard Beachfront Condo in Oak Bluffs
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy all that Martha's Vineyard has to offer in this spacious two bedroom, two full bath beautifully furnished condo ov ...
From $424 per night (USD)
VRBO
From $660 per night (USD)
Expedia
Spacious Waterview Condo - Steps To The Beach, Right Across The Street!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Prime location close to the center of town in the fabulous SeaView Condo building in the heart of Oak Bluffs. Highly des ...
From $660 per night (USD)
Expedia
From $1407 per night (USD)
VRBO
Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Ask about Discounts if 8 or fewer guests. ...
From $1407 per night (USD)
VRBO
From $1819 per night (USD)
VRBO
7/6-7/13 AVAILABLE DUE TO LAST MINUTE CANCELLATION! Walk to Beach!
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
LAST MINUTE CANCELLATION FOR JULY 6TH - 13TH, 2025!! This charming Vineyard home just completed a large renovation incl ...
From $1819 per night (USD)
VRBO
From $801 per night (USD)
VRBO
The quintessential MV home. Now booking for 2025!
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Pirate's Cove is a young, Victorian-style home, designer-decorated and nestled on a quiet lane in East Chop, located jus ...
From $801 per night (USD)
VRBO
From $466 per night (USD)
VRBO
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! A/C,Large Deck,Gazebo,Yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you ...
From $466 per night (USD)
VRBO
From $884 per night (USD)
VRBO
Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Victorian Cape Cod Cottage located in the highly desired Oak Bluffs Copeland District in Martha's Vineyard. Large family ...
From $884 per night (USD)
VRBO
From $396 per night (USD)
VRBO
Charming Oak Bluffs Cottage: Prime Location, Stylish Comfort & Serene Privacy
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your Vineyard getaway! Nestled in a peaceful neighborhood in Oak Bluffs, this cozy two-bedroom, one-bath cott ...
From $396 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Historic Home in East Chop
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Renovated home in East Chop, Oak Bluffs, Martha’s Vineyard. Built in 1872 by my great, great grandfather, the house has ...
From $586 per night (USD)
VRBO
From $585 per night (USD)
VRBO
Oak Bluffs Retreat - The perfect getaway!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Six minute drive to beach! This two floor beauty with central AC boasts ample yard space and all the amenities you look ...
From $585 per night (USD)
VRBO
From $1237 per night (USD)
VRBO
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2025!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Pirate's Reef is a NEW and beautifully decorated residence that offers 5 spacious bedrooms (2 master suites!) with 4.5 b ...
From $1237 per night (USD)
VRBO
From $1753 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 $1753 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Lovely vacation home within walking distance to Oak Bluffs and the beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your summer vacation home! This is a 3 bedroom 2 1/2 bath home located less than a mile from downtown Oak Bl ...
From $606 per night (USD)
VRBO
From $596 per night (USD)
Expedia
Oak Bluffs - Quiet neighborhood
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Less than a mile from downtown, harbor and beach. Located in a quiet neighborhood, guests are sure to enjoy a memorable ...
From $596 per night (USD)
Expedia
From $768 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 $768 per night (USD)
VRBO
$A BRILLANT WAY\nCentral Location To Beach/Shops/Restaurants/Arcade/Family Bowling$
From $586 per night (USD)
VRBO
A BRILLANT WAY\nCentral Location To Beach/Shops/Restaurants/Arcade/Family Bowling
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A Brillant Way is a Brilliant Condo located in the heart of Oak Bluffs. Second level has 2 bedrooms - Queen size bed in ...
From $586 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Oak Bluffs Cutie Near Beach + Town Center! Ferry tix available for some dates!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy both worlds - a peaceful atmosphere with many comfortable places to escape to read, nap or chat, near the heart of ...
From $439 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Oak Bluffs Gingerbread Cottage near Downtown, Beach, Ferry and Ocean Park!
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
- Magnificent front porch for rocking and peaceful island observations! - All furniture is whimsical and light to match ...
From $643 per night (USD)
VRBO
From $507 per night (USD)
VRBO
Perfect Home For A Family Vacation With All The Amenities
Bedrooms:
4
Bathrooms:
4
Sleeps:
13
This professionally designed & decorated vacation home is great for a quiet get away for one or two couples/families or ...
From $507 per night (USD)
VRBO
From $439 per night (USD)
VRBO
Spacious family house, short walk to the Lagoon & close to Oak Bluffs center
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The 'Anchor Inn' on Carole Avenue is the perfect spot for your family to relax and enjoy the Vineyard! The home is a 4 ...
From $439 per night (USD)
VRBO
From $303 per night (USD)
VRBO
Held July weeks open & discounted! Updated Oak Bluffs home! Close to everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This home was updated in 2023! Beautiful detached 2 bedroom within walking distance to the center of Oak Bluffs. The ext ...
From $303 per night (USD)
VRBO
From $1080 per night (USD)
VRBO
OB Watrfront 4+ BR. Quiet/Walk to Town. Beachy, classic, great ocean/pond views.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Best of everything: We are located on the back side of Farm Pond, which overlooks Harthaven, Nantucket Sound, and Chappa ...
From $1080 per night (USD)
VRBO
$\The Carousel House\ - Ocean Park - Featured in New York Times$
From $1882 per night (USD)
VRBO
\"The Carousel House\" - Ocean Park - Featured in New York Times
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This house, built in 1865, was featured in the New York Times article on Oak Bluffs, 'The President Was Here (Grant, Tha ...
From $1882 per night (USD)
VRBO
From $1189 per night (USD)
VRBO
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
GAME ROOM!!! We have converted the room in the garage as a place where our guests can go should you have a rainy day or ...
From $1189 per night (USD)
VRBO
From $693 per night (USD)
VRBO
Ocean Views from East Chop
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Easy access to Oak Bluffs or Vineyard Haven, quiet street overlooking Crystal Lake and the Vineyard Sound. House has fi ...
From $693 per night (USD)
VRBO
From $950 per night (USD)
VRBO
Multiple Ensuites, Central Air, Perfect Location
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our home is approximate 2200sf and has 4 bedrooms including 3 bedrooms with en-suite bathrooms (all on second floor) an ...
From $950 per night (USD)
VRBO
From $1053 per night (USD)
VRBO
Gingerbread cottage with stunning Oak Bluffs Harbor View
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Amazing vacation spot Enjoy beautiful views of Oak Bluffs Harbor and beyond Historic gingerbread cottage Large front por ...
From $1053 per night (USD)
VRBO
From $748 per night (USD)
VRBO
Beautiful cape located 2 blocks from Lagoon!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
It's all about Location!!! This cape style home is located on a quiet road very close to the Lagoon in Oak Bluffs and is ...
From $748 per night (USD)
VRBO
From $773 per night (USD)
VRBO
Location, Location, Location- Updated East Chop Year Round Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oak Bluffs: Located in East Chop! Beautiful year round home steps to Oak Bluffs Harbor, East Chop Beach Club, Jetty Beac ...
From $773 per night (USD)
VRBO
From $610 per night (USD)
VRBO
Charming Island House-Close to Ginger Bread Cottages, Beaches, Shops...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come experience the magic of the Vineyard in our island home. This charming residence is clean, cozy and boasts modern f ...
From $610 per night (USD)
VRBO
From $2146 per night (USD)
VRBO
Relaxing Beach Front Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Perfect Vineyard Vacation: This beautiful beachfront home is on the east side of Lagoon Pond, in the town of Oak Blu ...
From $2146 per night (USD)
VRBO
From $456 per night (USD)
VRBO
Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car prkng
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Lovely private first floor of raised ranch house. Sleeps Four in 2 bedrooms (queen and two singles). One and a half bat ...
From $456 per night (USD)
VRBO
From $906 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 $906 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Convenient In-Town (Oak Bluffs) Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Great Vineyard location on Vineyard Avenue in Oak Bluffs. Built in 1920 and thoughtfully restored in 1999, this house is ...
From $643 per night (USD)
VRBO
From $1277 per night (USD)
VRBO
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 $1277 per night (USD)
VRBO
From $334 per night (USD)
Expedia
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 $334 per night (USD)
Expedia
Click For Pricing
VRBO
Cute 4-BR House within walking distance of Circuit Avenue
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
It is all about location! Leave the car at the house, and walk right into town. This 4 bedroom, 2 bath home features a l ...
Click For Pricing
VRBO
From $718 per night (USD)
VRBO
Completely renovated, air conditioned cottage close to the beach. Dog friendly.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This property has something for the whole family to enjoy. A large wrap-around porch, screened in dining area on side po ...
From $718 per night (USD)
VRBO
From $567 per night (USD)
VRBO
Location, Charm, & Steps to Town/Beach -- Central AC, 100% Renewable Energy
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
(Note: for 2025, we are renovating the upstairs bath and creating a more spa-like shower. New Photos by late March, rou ...
From $567 per night (USD)
VRBO
From $4032 per night (USD)
VRBO
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
6 Bedrooms, Sleeping Porch, 3 Full Baths, 2 Half Baths, Sleeps 12+ A timeless Martha’s Vineyard escape awaits you at th ...
From $4032 per night (USD)
VRBO
From $1229 per night (USD)
VRBO
Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy everything the island has to offer in a spacious, custom-built, fully-stocked modern farmhouse and backyard oasis ...
From $1229 per night (USD)
VRBO
From $489 per night (USD)
VRBO
Close to town, beautifully updated
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*** For stays between 9/1/2024 and 6/14/2025, Please inquire about a discounted cleaning rate***. Renovated Oak Blu ...
From $489 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Comfortable Island Home, Easy Access to Beaches and Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Salt Box style Log Home with open floor plan built by my family with a country feel, located on a wooded lot in the down ...
From $454 per night (USD)
VRBO
From $525 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 $525 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Delilah & Joseph Pierce House
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Travel and Enjoy! Built by international artist, curator, educator, advocate, and diplomat Delilah W. Pierce, and her fa ...
From $492 per night (USD)
VRBO
From $767 per night (USD)
Expedia
Dog-friendly home with fenced yard- walking distance to beach, ferry & town
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Wayland Victorian Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $767 per night (USD)
Expedia
From $1602 per night (USD)
VRBO
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 $1602 per night (USD)
VRBO
From $1117 per night (USD)
VRBO
Waterfront Home in Oak Bluffs - Walk to Town and Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This lovely four-bedroom shingled Cape overlooks Farm Pond, Harthaven, and Nantucket Sound. It is a vintage cottage com ...
From $1117 per night (USD)
VRBO
From $458 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 $458 per night (USD)
VRBO
From $307 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 $307 per night (USD)
Expedia
From $449 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 $449 per night (USD)
VRBO
From $346 per night (USD)
VRBO
In-Town Certified National Historic Oak Bluffs Property -
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the ...
From $346 per night (USD)
VRBO
From $785 per night (USD)
VRBO
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 $785 per night (USD)
VRBO
From $560 per night (USD)
VRBO
Oak Bluffs Cottage - A Short Walk to the Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Stay in this beautiful Vineyard home and enjoy a relaxing vacation back in time! Within 5 minutes of stepping out the f ...
From $560 per night (USD)
VRBO
From $525 per night (USD)
VRBO
Water View Oasis 1 mi from Oak Bluffs 10 min Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Beautiful water view, spacious natural landscape, and privacy enhance the serenity of our rustic barn-style home tucked ...
From $525 per night (USD)
VRBO
From $342 per night (USD)
Expedia
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 $342 per night (USD)
Expedia
From $380 per night (USD)
VRBO
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 $380 per night (USD)
VRBO
From $745 per night (USD)
Expedia
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 $745 per night (USD)
Expedia
From $423 per night (USD)
VRBO
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)
VRBO
From $452 per night (USD)
VRBO
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Bedrooms:
0
Bathrooms:
2
Sleeps:
6
Mid-century rustic cottage charm tucked on 3 acres 1 mi to Oak Bluffs and Vineyard Haven center's. Acquired in 1950 by L ...
From $452 per night (USD)
VRBO
From $1376 per night (USD)
VRBO
Walk to Beach and Town. Large Family House.
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
-Seven air conditioned bedrooms -Four bathrooms -One living room and two small sitting rooms -large bluestone patio wit ...
From $1376 per night (USD)
VRBO
From $663 per night (USD)
VRBO
WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! Deck,A/C,Outdoor Shower, Wifi
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
***IMPORTANT--PLEASE "MESSAGE " HOST FIRST----BEFORE SENDING A BOOKING REQUEST!! ( JUST CLICK ON " CONTACT HOST" (you w ...
From $663 per night (USD)
VRBO
From $369 per night (USD)
VRBO
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 $369 per night (USD)
VRBO
From $393 per night (USD)
Expedia
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 $393 per night (USD)
Expedia
From $837 per night (USD)
VRBO
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 $837 per night (USD)
VRBO
From $503 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 $503 per night (USD)
VRBO
From $335 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 $335 per night (USD)
VRBO
From $553 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 $553 per night (USD)
Expedia
From $569 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 $569 per night (USD)
VRBO
From $329 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 $329 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $1370 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 $1370 per night (USD)
Expedia
From $2498 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 $2498 per night (USD)
VRBO
From $418 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 $418 per night (USD)
VRBO
From $1192 per night (USD)
VRBO
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 $1192 per night (USD)
VRBO
From $2327 per night (USD)
VRBO
Waterfront House On Oak Bluffs Harbor
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Rarely available, large 5 bedroom home with 2 bathrooms and an outside shower right on Oak Bluffs Harbor. Great for fami ...
From $2327 per night (USD)
VRBO
From $659 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 $659 per night (USD)
VRBO
From $500 per night (USD)
Expedia
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 $500 per night (USD)
Expedia
From $1340 per night (USD)
VRBO
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 $1340 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Spacious 1 Bedroom Apt - 3 min Walk to the Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A perfect place for 1-4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dinin ...
From $251 per night (USD)
VRBO
From $305 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 $305 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 $563 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 $563 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $1023 per night (USD)
VRBO
Now booking Summer 2026!! 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 $638 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 $638 per night (USD)
VRBO
From $1457 per night (USD)
VRBO
Discount last week July Reduced Oak Bluffs walk to Circuit Ave & Inkwell Beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Surround yourself with comfort and fresh furnishings! This is a beautiful five-year-old home that is stylishly furnishe ...
From $1457 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1685 per night (USD)
VRBO
The Island Collection MV: Enjoy This 1850s Victorian Home With Ocean Views!
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 $1685 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 $614 per night (USD)
VRBO
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 $614 per night (USD)
VRBO
From $447 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 $447 per night (USD)
VRBO
From $1245 per night (USD)
VRBO
Historic, dog-friendly beach view house with fast WiFi, ocean view, & grill
Bedrooms:
4
Bathrooms:
6
Sleeps:
11
Captain Shaw Norris House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $1245 per night (USD)
VRBO
From $316 per night (USD)
Expedia
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 $316 per night (USD)
Expedia
From $1530 per night (USD)
VRBO
Soulas Martha's Vineyard Victorian Beach House, Walk to Inkwell Beach & Town
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 $1530 per night (USD)
VRBO
From $1083 per night (USD)
VRBO
Air conditioned Oak Bluffs WATERVIEW Victorian. steps from beach. BIG porch.
Bedrooms:
2
Bathrooms:
6
Sleeps:
13
*** CONTACT HOST TO CONFIRM DATES BEFORE BOOKING**** *** CONTACT HOST FOR EARLY BIRD SPECIAL AND OFF-SEASON RATES*** * ...
From $1083 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 $405 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 $405 per night (USD)
Expedia

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