Island holiday rentals in New England

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Top-rated island rentals in New England

Guests agree: these island rentals are highly rated for location, cleanliness and more.

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Superhost

Home in Shrewsbury

4.9 out of 5 average rating, 20 reviews

Lake "Island" near Boston

This place is a hidden gem! It is a lake peninsula. Enjoy the amazing lifestyle on Lake Quinsigamond, while being only 10min from the center of Worcester. Even if you come to work in the area it feels like being on vacation. Lots of fun things all year around and only 40min to Boston, 1.5hr to Cape Cod beaches. This 2 bedroom A-frame house and 1 BDR cabin are on a 5 acres property (2,000 feet of shoreline). Very close to UMass hospital, grocery stores, gym, restaurants, route 20 and I-90.

Guest favourite

Cabin in Paul Smiths

4.91 out of 5 average rating, 23 reviews

Mrs. Otis's Cabin with Woodland View

In the tradition of the Adirondack Great Camps - magnificent rustic compounds of comfort built a century ago by the rich and powerful on wilderness estates. White Pine Camp offers a year round restful retreat in unparalleled natural surroundings. Here, in the heart of the Adirondacks the largest protected wilderness in the continental United States, guests receive the key to peace and tranquility, a place to recharge the spirit. As a guest, you have your choice of 13 distinctive cabins

Guest favourite

Cottage in Tremont

4.89 out of 5 average rating, 97 reviews

Sealport Cottage: Full week Saturday-Saturday only

Sealport Ocean Cottage is a magical place with sparkly days and starry nights! Beautiful ocean views of Seal Cove, Blue Hill Bay on the "Quietside" of this island. Rustic, family owned for 60+ years, this comfy, quiet summer only cottage is all yours to enjoy sunsets, days on the porch, woods and seashore near Acadia National Park. Weekly rentals Saturday to Saturdays only: check-in 4pm or later, check-out 10am, with 5 safety hours between guests for professional cleanings, relax & enjoy!

Guest favourite

Cottage in Chertsey

4.86 out of 5 average rating, 51 reviews

The Chalets of Lac Grenier – Island

Les Chalets du Lac Grenier offers 7 luxury cottages for rent located on a 35 acre waterfront estate. Our cottages are completely furnished and are available for rental year round. All our cottages are waterfront, on large wooded lots (averaging 51,000 square feet each). The resort is one hour's drive from Montreal in Lanaudière. An outdoor spa is located on the resort. It is opened year round and has an exceptional view of the lake. It is available to all our clients of the resort.

Guest favourite

Farm stay in Westport Island

4.84 out of 5 average rating, 128 reviews

The Stilt House

Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

Top guest favourite

Home in Friendship

5 out of 5 average rating, 90 reviews

Vintage ISLAND farmhouse, BYO boat/kayak. Unique!

A Midcoast Maine island paradise. Bring (or rent) your boat/kayak and taste for adventure. Secluded circa-1850 saltwater farmhouse, 1/4-mile private shore. No plumbing (outhouse, rain-barrel showers). No electricity (candles, lamps, flashlights; solar phone-charging). One mile from Friendship Harbor town landing. Beach, wharf, boathouse, forest trails, blueberries, kayak adventures, dark night skies, lobsters, peace, quiet. Note: Inaccessible at dead-low tide.

Superhost

Home in Yarmouth

4.88 out of 5 average rating, 146 reviews

Eagle's Nest on 8 acres next little john preserve

Nestled on 8 acres overlooking Casco Bay, the Eagle's Nest cottage has 1 bedroom and 1 bathroom. Open plan with full-kitchen and living room including a queen-size sofa bed. Located on an island, you're only 20 minutes from downtown Portland and 10 minutes from downtown Yarmouth. Last but not least the cottage is a 5-minute walk from a 23-acre preserve that has numerous scenic viewpoints, tide pools and ledges, and picnic tables. Coastal Maine at its best!

Superhost

Island in Cumberland

4.89 out of 5 average rating, 79 reviews

Island Cottage Getaway in Casco Bay!!

Log cabin includes a master bedroom, loft w/4 beds & a small room with bunkbeds. It has solar power, a bathroom/hot shower, kitchen, dining room, den, living room, & a big private yard. It's close to the Portland airport, close to 5 star restaurants, and is on the outskirts of a beautiful harbor. There are only a few other cabins and no roads on the island. Island fun such as fishing, swimming, camping and exploring will keep you busy for your stay.

Guest favourite

Island in Saint-Adolphe-d'Howard

4.96 out of 5 average rating, 57 reviews

Quiet private island! New SPA and Sauna!

New in 2024 – Thermal experience with private HOT TUB and SAUNA on the island! Private island for your exclusive use on a lake with exceptional water quality and surrounded by forest. Accessible in summer and winter. In summer, you can enjoy a private pontoon for crossing and your exclusive use on the lake. During the winter, the island is accessible on foot on the ice. Fully equipped cottage with many activities available year-round.

Guest favourite

Island in Pine Plains

4.93 out of 5 average rating, 91 reviews

Private Island on Twin Island Lake

Embark on an off-grid luxury glamping adventure in the heart of Hudson Valley, discover one of Twin Island Lake’s private island with 360 degree views.. Reconnect with yourselves and nature in a Safari style tent furnished with a queen size bed. 13x10 gazebo with outdoor amenities. Park on the mainland next to the dock where a canoe awaits your arrival. This sweet escape is a once in a lifetime experience you will remember forever.

Top guest favourite

Island in Monmouth

4.98 out of 5 average rating, 249 reviews

Naughty Dog Private Island Log Cabin

Be all alone on this remote island with 1400 acres of Annabessacook Lake as your backyard. Enjoy pristine surroundings, a rustic, off-the-grid log cabin, with solar lighting and a hot shower. Swimming, boating, fishing, birding, and relaxing by the fire - do it all (or not). Prepare for adventure! Pack light: Bring your vacay clothes, pups, favorite food, & be ready for a blissful, private island get away. It's AWAY away.

Guest favourite

Campsite in Penobscot

4.98 out of 5 average rating, 127 reviews

Private Lakeside Camping in Penobscot, Maine

Private lakeside camping on Toddy pond in Penobscot, Maine 50 min. from Acadia and Bar Harbor. This 400 foot private wooded lakeside lot is available for camping. This rental is close to Acadia, Ellsworth, Bucksport and the Blue Hill Peninsula. Go out and explore the area attractions or stay put and swim, fish, and kayak on one of Downeast Maine's most popular lakes; Toddy Pond.