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 $428 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 $428 per night (USD)
VRBO
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Expedia
Martha's Vineyard Home w/ Deck < 1 Mi to Beach!
Bedrooms:
2
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 ...
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Expedia
From $1229 per night (USD)
VRBO
Famous Gingerbread House named Seashrimp across from Oak Bluffs Harbor
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Year-round in-town Historical Famous Seashrimp Gingerbread House across from harbor/Nancy's all on the water restaurants ...
From $1229 per night (USD)
VRBO
From $705 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 $705 per night (USD)
Expedia
From $1407 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 $1407 per night (USD)
VRBO
From $1854 per night (USD)
VRBO
Daniels House is your next vacation home in Oak Bluffs.
Bedrooms:
6
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 $1854 per night (USD)
VRBO
From $723 per night (USD)
VRBO
Charming Oak Bluffs Retreat – Walk to Town, Harbor & More
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Just outside downtown Oak Bluffs, this 3-bedroom, 2.5-bath home features Central AC and an open layout ideal for gatheri ...
From $723 per night (USD)
VRBO
From $961 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 $961 per night (USD)
Expedia
From $962 per night (USD)
VRBO
Oceanview East Chop Beach House - 4 Bed/2 Bath - 5 min walk to beach
Bedrooms:
1
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 $962 per night (USD)
VRBO
From $628 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 $628 per night (USD)
Expedia
From $526 per night (USD)
VRBO
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Gingerbread Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $526 per night (USD)
VRBO
From $565 per night (USD)
Expedia
Family-built Oak Bluffs property in a wonderful location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Frazier Circle, Unit 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $565 per night (USD)
Expedia
From $1214 per night (USD)
VRBO
Family-built Oak Bluffs property in a great location with kitchens & hot tub
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Frazier Circle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1214 per night (USD)
VRBO
From $726 per night (USD)
Expedia
Family-built Oak Bluffs property in a wonderful location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Frazier Circle, Unit 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $726 per night (USD)
Expedia
From $830 per night (USD)
VRBO
New 2 min from Circuit ave
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
* new for 2025: Gameroom with pool table and ping pong table. * Welcome to this beautifully renovated home, located wit ...
From $830 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Charming cottage near the beach with a furnished deck, yard, & washer/dryer
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Birds of Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $572 per night (USD)
Expedia
From $870 per night (USD)
VRBO
Walk to town & beach A/C, Strong WiFi, family & pet friendly. Outdoor shower
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summertime! And the living is easy in this comfortable, casual home on Martha's Vineyard. The large front deck is great ...
From $870 per night (USD)
VRBO
From $620 per night (USD)
Expedia
Spacious colonial home close to town with AC, porches, & W/D
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Seabreeze Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $620 per night (USD)
Expedia
From $955 per night (USD)
VRBO
Charming, Victorian in East Chop
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax with the whole family at this peaceful place to stay. Ideally located in East Chop, in walking distance to the B ...
From $955 per night (USD)
VRBO
From $1214 per night (USD)
VRBO
Vineyard Social-Spacious 5BR Home in Oak Bluffs
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fant ...
From $1214 per night (USD)
VRBO
From $366 per night (USD)
VRBO
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Book your next East Coast escape at this Oak Bluffs vacation rental! Conveniently located near downtown Oak Bluffs, this ...
From $366 per night (USD)
VRBO
From $871 per night (USD)
Expedia
Spacious home in central location with beautiful patio, pool table, W/D, & AC
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Bird Street Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $871 per night (USD)
Expedia
From $518 per night (USD)
VRBO
September 2025 Available! 6 Beds! Near Ocean Park, Inkwell, Ferry, Flying Horses
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
6 Bedrooms with incredible location will comfortably allow your family to vacation in the best part of Oak Bluffs. The l ...
From $518 per night (USD)
VRBO
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Expedia
GingerBread Cottage at Oak Bluffs
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Resort may charge damage deposit fees, cleaning fees, activities fees, and applicable Resort lodging taxes. Intimate Ho ...
Click For Pricing
Expedia
From $263 per night (USD)
VRBO
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
July and August: Turnover day is generally Friday. This lovely, in-town, impeccably renovated 1800's historic Oak Bluff ...
From $263 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 $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
$\The Carousel House\ - Ocean Park - Featured in New York Times$
From $1862 per night (USD)
Expedia
\"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 $1862 per night (USD)
Expedia
From $2170 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 $2170 per night (USD)
VRBO
From $1097 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 $1097 per night (USD)
VRBO
From $274 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 $274 per night (USD)
VRBO
From $947 per night (USD)
VRBO
Inca Gardens Apt. New To Market - Lg Patio - Pets
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Inca Gardens is a 2nd-floor apartment of a cute house located in a quiet area of Martha's Vineyard between Oak Bluffs an ...
From $947 per night (USD)
VRBO
From $2456 per night (USD)
VRBO
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This quintessential Vineyard cottage was built in the 1920's, and retains most of its original charm and character. Loca ...
From $2456 per night (USD)
VRBO
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Expedia
Remodeled and historic, beautiful Oak Bluffs home. Walk to Town and Ferry.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This is a beautifully remodeled, and meticulously maintained house in Cottage City. The property is a short walk to town ...
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Expedia
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VRBO
Luxury Loft Historic Center Oak Bluffs
Bedrooms:
2
Bathrooms:
6
Sleeps:
13
This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are do ...
Click For Pricing
VRBO

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Lakeside Park Rentals

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Results: 235 Rentals