Island holiday rentals in New England

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.

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!

Les Chalets du 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.

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.

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.

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!

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.

Flagstaff Lakefront-Near Sugarloaf Vacation Home

Large, comfortable four season home on Flagstaff Lake, facing Sugarloaf & Bigelow Preserve Mountains. Three acres of land on dead-end road with private waterfront access, gazebo, firepit & dock on Flagstaff Lake. Canoe, kayak, swim and fish, all from property. Beautiful views of Lake & nearby mountains throughout the house. This 3 bed/2 bath gem is a great house for both single and multi-families!

Naughty Dog Private Island Log Cabin

Naughty Dog Island is what happens when island time meets unapologetic canine freedom. This is a private island log cabin where you and your pup can truly be away away — no leashes once you arrive, no neighbors, no schedules worth keeping. Just you, your dog(s), and a 1,400-acre lake that becomes your shared backyard. If your dog has ever dreamed of running the show, this is their moment.

Unique chalet sur une Île privée - tranquillité !

Île privative à votre usage exclusif sur un lac avec une qualité d’eau exceptionnelle et entourée de forêt. Accessible en été comme hiver. En été, vous profitez d’un ponton privatif pour la traverse et votre usage exclusif sur le lac. Durant l’hiver, l’ile est accessible à pied sur la glace (>15 cm). Chalet complètement équipé avec de nombreuses activités disponibles toute l’année.

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.

1 Acre Private Island Cottage (Sat Check In/Out)

Get brought out to the island on a Saturday, you and your dogs can enjoy a vacation on your own private island. And then get picked up a week later on Saturday. A week to swim, fish, bird watch, camp fires, grilling, kayaks, the works. Full functioning kitchen, indoor shower, outdoor shower, screened porch, 10 minute canoe to shore, canoe provided.