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 $538 per night (USD)
VRBO
Oak Bluffs Cottage - A Short Walk to the Beach!
Bedrooms:
3
Bathrooms:
4
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 $538 per night (USD)
VRBO
From $832 per night (USD)
Expedia
Water View Oasis 1 mi from Oak Bluffs 10 min Walk to Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful water view, spacious natural landscape, and privacy enhance the serenity of our rustic barn-style home tucked ...
From $832 per night (USD)
Expedia
From $1005 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 $1005 per night (USD)
VRBO
From $446 per night (USD)
Expedia
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 $446 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Delilah & Joseph Pierce House
Bedrooms:
1
Bathrooms:
3
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 $966 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 $966 per night (USD)
Expedia
From $737 per night (USD)
VRBO
Completely renovated, air conditioned cottage close to the beach. Dog friendly.
Bedrooms:
4
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 $737 per night (USD)
VRBO
$Location, Charm, & Steps to Town\/Beach -- Central AC, 100% Renewable Energy$
From $623 per night (USD)
Expedia
Location, Charm, & Steps to Town\/Beach -- Central AC, 100% Renewable Energy
Bedrooms:
2
Bathrooms:
5
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 $623 per night (USD)
Expedia
From $4319 per night (USD)
VRBO
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Bedrooms:
3
Bathrooms:
7
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 $4319 per night (USD)
VRBO
$Modern 4 bed\/3.5 bath Farmhouse, private HEATED POOL and AC on bike path$
From $1362 per night (USD)
Expedia
Modern 4 bed\/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Enjoy everything the island has to offer in a spacious, custom-built, fully-stocked modern farmhouse and backyard oasis ...
From $1362 per night (USD)
Expedia
From $766 per night (USD)
VRBO
Close to town, beautifully updated
Bedrooms:
3
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 $766 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Comfortable Island Home, Easy Access to Beaches and Town
Bedrooms:
1
Bathrooms:
3
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 $643 per night (USD)
VRBO
Convenient In-Town (Oak Bluffs) Location
Bedrooms:
2
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
$Modern, luxury 5-bed, 4.5-bath w\/full basement! Now booking for 2025!$
From $1585 per night (USD)
Expedia
Modern, luxury 5-bed, 4.5-bath w\/full basement! Now booking for 2025!
Bedrooms:
5
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 $1585 per night (USD)
Expedia
$Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living \/dining rm 2 car prkng$
From $533 per night (USD)
VRBO
Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living \/dining rm 2 car prkng
Bedrooms:
2
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 $533 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Lovely vacation home within walking distance to Oak Bluffs and the beach
Bedrooms:
3
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 $590 per night (USD)
Expedia
From $620 per night (USD)
VRBO
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 $620 per night (USD)
VRBO
From $565 per night (USD)
Expedia
Beautiful Contemporary Farmhouse close to Oak Bluffs
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Beautifully maintained contemporary farmhouse features an open floor plan. The first floor has an open kitchen, dining, ...
From $565 per night (USD)
Expedia
From $1189 per night (USD)
VRBO
CENTRAL AIR! Quiet East Chop Retreat Walk 2 Town and Beach.
Bedrooms:
3
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)
Expedia
Ocean Views from East Chop
Bedrooms:
5
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)
Expedia
From $967 per night (USD)
VRBO
Multiple Ensuites, Central Air, Perfect Location
Bedrooms:
4
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 $967 per night (USD)
VRBO
From $1252 per night (USD)
Expedia
Gingerbread cottage with stunning Oak Bluffs Harbor View
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Amazing vacation spot Enjoy beautiful views of Oak Bluffs Harbor and beyond Historic gingerbread cottage Large front por ...
From $1252 per night (USD)
Expedia
From $748 per night (USD)
VRBO
Beautiful cape located 2 blocks from Lagoon!
Bedrooms:
3
Bathrooms:
4
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 $750 per night (USD)
Expedia
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 $750 per night (USD)
Expedia
From $753 per night (USD)
VRBO
Charming Island House-Close to Ginger Bread Cottages, Beaches, Shops...
Bedrooms:
3
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 $753 per night (USD)
VRBO
$A BRILLANT WAY\nCentral Location To Beach\/Shops\/Restaurants\/Arcade\/Family Bowling$
From $607 per night (USD)
Expedia
A BRILLANT WAY\nCentral Location To Beach\/Shops\/Restaurants\/Arcade\/Family Bowling
Bedrooms:
2
Bathrooms:
3
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 $607 per night (USD)
Expedia
From $558 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 $558 per night (USD)
VRBO
From $609 per night (USD)
Expedia
Oak Bluffs Gingerbread Cottage near Downtown, Beach, Ferry and Ocean Park!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
- Magnificent front porch for rocking and peaceful island observations! - All furniture is whimsical and light to match ...
From $609 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Perfect Home For A Family Vacation With All The Amenities
Bedrooms:
5
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 $535 per night (USD)
VRBO
From $547 per night (USD)
Expedia
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 $547 per night (USD)
Expedia
From $407 per night (USD)
VRBO
2025 NOW OPEN! 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 $407 per night (USD)
VRBO
$OB Watrfront 4+ BR. Quiet\/Walk to Town. Beachy, classic, great ocean\/pond views.$
From $949 per night (USD)
Expedia
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 $949 per night (USD)
Expedia
From $671 per night (USD)
VRBO
Martha's Vineyard Beachfront Condo in Oak Bluffs
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy all that Martha's Vineyard has to offer in this spacious two bedroom, two full bath beautifully furnished condo ov ...
From $671 per night (USD)
VRBO
From $787 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 $787 per night (USD)
Expedia
From $1745 per night (USD)
VRBO
Glorious Sunsets and Fun on Private Waterfront in Beautiful, Comfortable Home.
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
FREE!!! A Transferable Round-trip SSA auto reservation is included for each remaining 2025 week booked in July and Aug ...
From $1745 per night (USD)
VRBO
$7\/6-7\/13 AVAILABLE DUE TO LAST MINUTE CANCELLATION! Walk to Beach!$
From $1851 per night (USD)
Expedia
7\/6-7\/13 AVAILABLE DUE TO LAST MINUTE CANCELLATION! Walk to Beach!
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
LAST MINUTE CANCELLATION FOR JULY 6TH - 13TH, 2025!! This charming Vineyard home just completed a large renovation incl ...
From $1851 per night (USD)
Expedia
From $1072 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 $1072 per night (USD)
VRBO
$WALK TO BEACHES,HARBOR,EVERYTHING!! IN-TOWN OB! A\/C,Large Deck,Gazebo,Yard$
From $429 per night (USD)
Expedia
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 $429 per night (USD)
Expedia
From $750 per night (USD)
VRBO
Large, Charming Vintage Cape Cod Cottage, 2 Blocks to Town and Beaches!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Victorian Cape Cod Cottage located in the highly desired Oak Bluffs Copeland District in Martha's Vineyard. Large family ...
From $750 per night (USD)
VRBO
From $424 per night (USD)
Expedia
Charming Oak Bluffs Cottage: Prime Location, Stylish Comfort & Serene Privacy
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
<p>Close to sailing, windsurfing, and more, this smoke-free cottage brings it all within reach. Oak Bluffs Harbor and Oa ...
From $424 per night (USD)
Expedia
$Historic Home in East Chop - Prime Summer Week Available 7\/6 - 7\/13\/25$
From $601 per night (USD)
VRBO
Historic Home in East Chop - Prime Summer Week Available 7\/6 - 7\/13\/25
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Renovated home in East Chop, Oak Bluffs, Martha’s Vineyard. Built in 1867 by my great, great grandfather, the house has ...
From $601 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Discover the magic of Martha’s Vineyard! NEW ! Build in 2020 !
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Build in 2020 ! New lovely studio apartment. Clean, bright and comfortable. 700 sq feet ! Great for couples, work trip ...
From $372 per night (USD)
Expedia
From $737 per night (USD)
VRBO
New to the rental market! Air conditioned family home, 1 mile from Circuit Ave
Bedrooms:
0
Bathrooms:
4
Sleeps:
10
New rental! Get away from it all in this Oak Bluffs secluded family friendly home offering 4 bedrooms, 2 full bathrooms, ...
From $737 per night (USD)
VRBO
From $965 per night (USD)
Expedia
Family friendly, walking distance to town, harbor, shops, restaurants, beaches
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Canary Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $965 per night (USD)
Expedia
From $1042 per night (USD)
VRBO
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Nestled in the charming town of East Chop, this 3-bedroom vacation home offers the perfect escape for your next getaway. ...
From $1042 per night (USD)
VRBO
Click For Pricing
Expedia
Vineyard charm island memories
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Great location,wonderful front porch,incredible kitchen,outdoor gas grill,walking distance to downtown,beaches,A/C,Marth ...
Click For Pricing
Expedia
$Quintessential Martha's Vineyard cottage with yard\/patio - walk to Inkwell Beach$
From $352 per night (USD)
VRBO
Quintessential Martha's Vineyard cottage with yard\/patio - walk to Inkwell Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Pinkletink Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $352 per night (USD)
VRBO
$COZY 3 BR\/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.$
From $774 per night (USD)
Expedia
COZY 3 BR\/2 BA CAPE COD IN QUIET NEIGHBORHOOD. CLOSE TO OB CENTER AND LAGOON.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in the beautiful Lagoon Heights neighborhood, you'll enjoy this lovely 3 Bedroom, 2 Bath cozy Cape Cod home with ...
From $774 per night (USD)
Expedia
From $518 per night (USD)
VRBO
In the heart of East Chop. Walks on East Chop Dr. Then relax on the private deck
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Great East Chop (Oak Bluffs) location! Take morning walks on world famous East Chop Drive, or watch the sunset from ther ...
From $518 per night (USD)
VRBO
$Dog-Friendly Downtown Home w\/Free WiFi, Deck, Water Views, & Partial A\/C$
From $472 per night (USD)
Expedia
Dog-Friendly Downtown Home w\/Free WiFi, Deck, Water Views, & Partial A\/C
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Marsh Walk Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $472 per night (USD)
Expedia
From $715 per night (USD)
VRBO
Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Bright air conditioned house has common space living TV room, dining and kitchen together. 1st floor has 1 bedroom with ...
From $715 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy Family Cottage Circuit Ave OB Walk to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Stay comfortably in Oak Bluffs at this 4-bedroom cottage. With 2 full beds a twin beds, this quaint property is perfect ...
Click For Pricing
Expedia
From $657 per night (USD)
VRBO
Charming studio with amazing location near town & beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Sankofa Studio Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $657 per night (USD)
VRBO
From $1107 per night (USD)
Expedia
Heart of Oak Bluffs - A Newly Renovated Gem, 5 Minute Walk to Town!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover the perfect blend of location and luxury in this beautifully renovated charmer, centrally situated in Oak Bluff ...
From $1107 per night (USD)
Expedia
$Charming home near downtown & beach with patio, outdoor shower, grill, & W\/D$
From $1199 per night (USD)
VRBO
Charming home near downtown & beach with patio, outdoor shower, grill, & W\/D
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Blissful Island Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $1199 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy vineyard cottage close to downtown with outdoor living space and amentiies.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
2 Decks, hot tub and close to everything. Has all new stainless appliances, wi-fi, cable, grill, about one mile walk t ...
Click For Pricing
Expedia
From $866 per night (USD)
VRBO
Location , Location , Location ! Walking distance to the beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Bellavista at the Seaview. This oceanfront condo is a coveted two bedroom , two bathroom home that was comple ...
From $866 per night (USD)
VRBO
From $1619 per night (USD)
Expedia
Spacious 5-bedroom house with AC and WiFi in brilliant Oak Bluffs
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Perched on a grassy hill, this majestic home has sweeping views of Oak Bluffs Harbor and is just minutes from East Chop ...
From $1619 per night (USD)
Expedia
From $1285 per night (USD)
VRBO
Oak Bluff's Victorian Walk to Town & Beaches
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
About this space First floor has AC and hosts windowed living, dining, work space, kitchen and garden apartment that sle ...
From $1285 per night (USD)
VRBO
$Oak Bluffs 3-Bedroom Victorian Cottage, Steps from Sunset Lake\/Park$
From $658 per night (USD)
Expedia
Oak Bluffs 3-Bedroom Victorian Cottage, Steps from Sunset Lake\/Park
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Step Into Vineyard history—with a modern twist. Originally part of the historic Methodist Campground in Oak Bluffs, this ...
From $658 per night (USD)
Expedia
From $697 per night (USD)
VRBO
Charming 3-Bedroom Home in the Heart of Oak Bluffs
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect Martha’s Vineyard getaway! Nestled in the heart of Oak Bluffs, this charming 3-bedroom home offe ...
From $697 per night (USD)
VRBO
$Charming 3-bedroom w\/loft.New Construction home with AC,WiFi. Short walk to town$
From $943 per night (USD)
Expedia
Charming 3-bedroom w\/loft.New Construction home with AC,WiFi. Short walk to town
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
This Oak Bluffs home boasts 3 inviting bedrooms and a cozy loft, including 2 king beds, 2 full beds and a queen sofa bed ...
From $943 per night (USD)
Expedia
From $1735 per night (USD)
VRBO
House with guest studio close to town and beach with grill, games, AC & patio
Bedrooms:
3
Bathrooms:
5
Sleeps:
9
Sankofa Martha's Vineyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $1735 per night (USD)
VRBO
From $1480 per night (USD)
Expedia
Modern Cottage Walk To Town & Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy one of Oak Bluffs’ newest accommodations perched at the peak of the Highlands boasting just a 10 minute walk to to ...
From $1480 per night (USD)
Expedia
From $866 per night (USD)
VRBO
Charming 3-bedroom house in Oak Bluffs with AC, WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to Noble House, your ideal getaway on Martha’s Vineyard. Nestled in the heart of Oak Bluffs at 21 Pheasant Lane, ...
From $866 per night (USD)
VRBO
From $983 per night (USD)
Expedia
Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to your home away from home! Experience the charm of Oak Bluffs in this spacious 3-bedroom, 2.5-bathroom beautif ...
From $983 per night (USD)
Expedia
From $661 per night (USD)
VRBO
Charming 3-bedroom house in OakBluffs, walking distance to Circuit Ave!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Nestled in Oak Bluffs, this delightful house offers 4 bedrooms including 1 king bed, 2 queen beds, and 1 bunk bed. With ...
From $661 per night (USD)
VRBO
From $686 per night (USD)
Expedia
Quiet Getaway Within Walking Distance Of All Oak Bluffs Has To Offer.
Bedrooms:
3
Bathrooms:
3
Sleeps:
5
An enchanting Cape Cod cottage nestled on a quiet road with Farm Pond and ocean views. Share family dinners and conversa ...
From $686 per night (USD)
Expedia
From $540 per night (USD)
VRBO
2-bedroom house, Short walk to beach, with AC and WiFi in Oak Bluffs
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Private Home and yard a block from the Lagoon in Oak Bluffs. Easy walk to quiet neighborhood beach. Brand new kitchen/ba ...
From $540 per night (USD)
VRBO
From $4038 per night (USD)
Expedia
Spacious 9-bedroom house with Waterview, WiFi, AC in delightful Oak Bluffs
Bedrooms:
5
Bathrooms:
9
Sleeps:
18
Get ready to relax in this 9-bedroom house in Oak Bluffs. This superb property boasts 3 king beds, 5 full beds, and 2 tw ...
From $4038 per night (USD)
Expedia
From $987 per night (USD)
VRBO
Peaceful East Chop Vineyard 5-BR 3-BA home, AC, large yard, Guest apt add-on.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Located in exclusive East Chop area of Oak Bluffs, enjoy what this 5-bedroom house has to offer. Walk to beach, a safe, ...
From $987 per night (USD)
VRBO
$Gorgeous 7BR\/6BA Ocean views Walk to Beach & Town - 10% off two week stay!$
From $2406 per night (USD)
Expedia
Gorgeous 7BR\/6BA Ocean views Walk to Beach & Town - 10% off two week stay!
Bedrooms:
6
Bathrooms:
7
Sleeps:
10
Large Private Home formerly known as the SeaSpray Inn and featured on the reality television show "The Vineyard", this l ...
From $2406 per night (USD)
Expedia
$Enchanting bungalow with golf nearby, full kitchen, central AC, & washer\/dryer$
From $764 per night (USD)
VRBO
Enchanting bungalow with golf nearby, full kitchen, central AC, & washer\/dryer
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
East Chop 90 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $764 per night (USD)
VRBO
From $753 per night (USD)
Expedia
Perfect location! Beach, Harbor & Town. Beautiful 1st Floor Apartment Oasis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This lovely, in-town, first-floor apartment is in a renovated 1800's historic Oak Bluffs cottage with a fenced in landsc ...
From $753 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Walk to OB Restaurants, Shopping, Harbor & Beaches! Winter monthly rental avail.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This beautiful, open concept, fully furnished home is just footsteps to Sunset Lake, harbor, beaches, entertainment, res ...
From $517 per night (USD)
VRBO
From $568 per night (USD)
Expedia
Family home located near everything needed for the perfect vacation.
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
The house was recently renovated with new appliances and other furnishing. Appliances include a convection oven, dishwas ...
From $568 per night (USD)
Expedia
From $2273 per night (USD)
VRBO
Vacation In This Historic And Luxurious Martha's Vineyard Home
Bedrooms:
6
Bathrooms:
8
Sleeps:
14
Perched on the corner of Ocean Park overlooking Nantucket Sound and across the street from the beach, this elegant home ...
From $2273 per night (USD)
VRBO
From $614 per night (USD)
Expedia
Charming, gracious cape 3 minute walk to private beach on Lagoon. Dog-friendly!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Lovely classic Vineyard cape located on a very quiet dead end street with access to a private sandy beach on the Lagoon. ...
From $614 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Make Lasting Memories In This Adorable Vineyard Cottage!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This quaint cottage, nestled in a quiet neighborhood of Oak Bluffs, is perfect for a romantic getaway, a special place t ...
From $288 per night (USD)
VRBO
$Fully Renovated & Spacious home walking distance to downtown Oak Bluffs\/Beaches$
From $698 per night (USD)
Expedia
Fully Renovated & Spacious home walking distance to downtown Oak Bluffs\/Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated three-level home with 3 bedrooms 2 bathrooms within walking distance to the heart of Downtown Oak Bluffs ...
From $698 per night (USD)
Expedia
From $870 per night (USD)
VRBO
OB Cozy-Cottage-Glam off Circuit with Great Outdoor living
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Location!!! Location!!! This updated cottage is a quick walk to town, beach, Tony’s Deli, tennis and basketball courts, ...
From $870 per night (USD)
VRBO
From $1027 per night (USD)
Expedia
Indulge in the ultimate vacation experience at this exquisite custom log home.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Turnover days are Saturday to Saturday Experience the ultimate in luxury and relaxation in the exclusive Eastville area ...
From $1027 per night (USD)
Expedia
$Renovated Historic House \The Legacy House\$
From $723 per night (USD)
VRBO
Renovated Historic House \"The Legacy House\"
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
2 Blocks - walking distance to Inkwell Beach! Walking distance to Circuit Avenue, Ocean Park, and Oak Bluffs ferry. Pea ...
From $723 per night (USD)
VRBO
$Coastal home with outdoor shower, grill, fireplace, central AC, & W\/D$
From $596 per night (USD)
Expedia
Coastal home with outdoor shower, grill, fireplace, central AC, & W\/D
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Yellow Brick Road House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $596 per night (USD)
Expedia
From $437 per night (USD)
VRBO
Tree Top Suite Get-Away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Our beautiful suite has a private entrance, is a walk down an old fashioned dirt road to a private beach and also right ...
From $437 per night (USD)
VRBO
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Expedia
Secluded but not Isolated home for all to enjoy
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
A lovely contemporary cape in East Chop with 3 bedrooms, loft & 2 full baths. High ceilings & skylights. A 1/2 mile walk ...
Click For Pricing
Expedia
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VRBO
3 BR cozy Vineyard Vacation Apartment
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 BR apartment located on Circuit Ave walking distance to town. This unit feels like its own house. The kitchen and livi ...
Click For Pricing
VRBO
From $1525 per night (USD)
Expedia
**Vineyard Vacation Retreat** -3 BR
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large ...
From $1525 per night (USD)
Expedia
From $1171 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 $1171 per night (USD)
VRBO
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Expedia
Cute 4-BR House within walking distance of Circuit Avenue
Bedrooms:
3
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
Expedia
$Fully Renovated & Spacious home within walking distance of Oak Bluffs \/ Beaches$
From $671 per night (USD)
VRBO
Fully Renovated & Spacious home within walking distance of Oak Bluffs \/ Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated three-level home with three bedrooms and two bathrooms within walking distance to the heart of Downtown ...
From $671 per night (USD)
VRBO
$Martha's Vineyard Home w\/ Deck < 1 Mi to Beach!$
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Expedia
Martha's Vineyard Home w\/ Deck < 1 Mi to Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Discover the beauty of Martha’s Vineyard when you stay at this charming 3-bedroom, 2.5-bathroom vacation rental! Situate ...
Click For Pricing
Expedia
From $1229 per night (USD)
VRBO
Famous Gingerbread Home the Seashrimp across from Harbor in downtown Oak Bluffs.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Year-round Oak Bluffs in-town Historical Famous Seashrimp Gingerbread House across from harbor/Nancy's all on the water ...
From $1229 per night (USD)
VRBO
From $753 per night (USD)
Expedia
Heart of Oak Bluffs, No Car Needed! Ocean Views, Walk to Everywhere!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to “Gem of the Ocean”! Martha’s Vineyard vacationers dream! This recently updated condo with private balcony and ...
From $753 per night (USD)
Expedia
From $1479 per night (USD)
VRBO
Martha’s Vineyard 7 Bedroom Vintage Home! 15 min walk to beaches and Oak Bluffs!
Bedrooms:
2
Bathrooms:
7
Sleeps:
14
Fantastic home available from May to October. Seven Bedrooms, one den with pull out couch, two bathrooms and a dreamy o ...
From $1479 per night (USD)
VRBO
From $2979 per night (USD)
Expedia
Daniels House is your next vacation home in Oak Bluffs.
Bedrooms:
7
Bathrooms:
9
Sleeps:
18
Breath taking views from this newly restored quintessential 1899 Oak Bluffs Cottage style home. It is equipped with 9 la ...
From $2979 per night (USD)
Expedia
From $843 per night (USD)
VRBO
Short walk to town!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Just on the outskirts of town in Oak Bluffs behind the Library is this lovely 3 Bedroom, 2.5 Bathroom home with Central ...
From $843 per night (USD)
VRBO
$Historical house with wraparound porch, modern updates, enclosed yard, & W\/D$
From $876 per night (USD)
Expedia
Historical house with wraparound porch, modern updates, enclosed yard, & W\/D
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Victorian by the Sea Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $876 per night (USD)
Expedia
$Oceanview East Chop Beach House - 4 Bed\/2 Bath - 5 min walk to beach$
From $1117 per night (USD)
VRBO
Oceanview East Chop Beach House - 4 Bed\/2 Bath - 5 min walk to beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
The perfect vacation awaits you at Frog Prince Cottage in beautiful East Chop, the finest neighborhood in Oak Bluffs. Ou ...
From $1117 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Spacious 4 BR Home, Steps to Lagoon, Minutes to Downtown Oak Bluffs and Beaches!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious two-level four-bedroom house within steps to lagoon located in Oak Bluffs and within minutes (2 Miles) to Downt ...
From $687 per night (USD)
Expedia

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