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Vacation rentals in Squirrel Island

Vacation rentals in Squirrel Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Squirrel Island

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

Decker Cove Winter Oasis
SUPERHOSTPrivate room · 2 guests · 1 bed · 1 private bathroom
Decker Cove Winter Oasis

Decker Cove Winter Oasis Our home is brand new, built in 2018, Radiant Heat and Central Air Conditioning. Enjoy the tranquility of a private bedroom and bathroom with separate entrance. Expanded queen Select Comfort Sleep Number bed, sitting area for two, microwave, coffee maker, peak at Decker Cove from sliding glass door entrance on farmer porch. Enjoy outdoor fire pit or coffee on the porch.

What guests are saying:

“This is a nice location just on Southport Island near Boothbay Harbor. It is close to a fabulous restaurant, Robinson's Warf and Tug Pub, and a couple of miles from Hendrick's Head lighthouse and beach area. Communication with the owners was very easy and they responded quickly to any questions we had. We will certainly stay there again when we are in the Boothbay Harbor region.”

Cliff House - Premier Ocean Front June Specials
Entire cottage · 6 guests · 4 beds · 2.5 bathrooms
Cliff House - Premier Ocean Front June Specials

Located in the Juniper Point community, Cliff House is both private and connected to the activities of a vibrant and welcoming traditional summer vacation resort. There is no more beautiful spot on the Maine coast. Comfortable both indoors and outdoors, it is full of light and charm, surrounded by ocean, trees, osprey, seagulls, seals and the occasional bald eagle. Within sight is a dock for swimming or boating, and up the road 200 yards are clay tennis courts. Wifi is excellent.

What guests are saying:

“Nestled on Juniper Point in the mid-coast Boothbay Region, Cliff House is truly special. It is a quintessential Maine summer cottage; welcoming and comfortable. It has commanding Southeast views and sits at the entrance to Townsend Gut that separates the peninsula from Southport Island. On weekends there's a never ending stream of pleasure boats going by and on weekdays, the lobster and working boats heading out for the day's catch and returning their haul to market. The central location makes it convenient to explore nearby points of interest. We made daytrips to the Boothbays, Wiscasset, Damariscotta, Pemaquid Pt., Bath, Brunswick, Ft. Popham and then spent an entire day driving up to and exploring Acadia National Park. The cottage has a stunning upper floor master suite with private bath and two other bedrooms (one with a private half bath) on the main floor. Everything we needed to cook up our own breakfasts and seafood dinners was available. Peaceful and quiet this is the place to disconnect from your devices, kick back on the deck and unwind. At night the stargazing is amazing! A stay at Cliff House allowed us to forget about our busy lives, for a time, and just immerse ourselves in the beauty all around us.”

Ocean Point Cushnoc Efficiency
Entire guest house · 2 guests · 2 beds · 1 bathroom
Ocean Point Cushnoc Efficiency

The Cushnoc Efficiency is a private one-room cottage at the heart of Ocean Point. Walking distance to the shore in three directions and adjacent to Ocean Point's social hub the "Casino"(Not a gambling casino, but a community social center) there is no better place to become acquainted with OP. Quiet and peaceful most of the year, yet lively during the heart of the summer, OP offers visitors breathtaking views of the local islands, spectacular surf during storms and truly phenomenal sunsets.

What guests are saying:

“When we first stumbled upon this efficiency on AirBnB, it seemed almost too good to be true. There must be a catch! But everything was as perfect as it seemed online. Ken and Melissa were the most thoughtful, gracious hosts. They provided us with all the information we needed and showed us around beautiful Ocean Point ! The efficiency is just perfect! Kitchen is compact and contains everything one needs. Everything was pristine and nicely decorated. The bed was very comfortable and the pull out futon was great as a second bed. The porch area was wonderful for sitting out and enjoying the coastal breeze. A very short walk to the water for a morning stroll or to enjoy the breathtaking sunsets. Location is incredible! We were fortunate to catch an amazing double rainbow after a brief rain shower! Just breathtaking! Ken and Melissa had excellent restaurant recommendations and were so helpful! They went way beyond to make our week comfortable and memorable. Thanks Ken and Melissa and Ocean Point ( Booth Bay) for a wonderful week!”

Holiday rentals for every style

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Popular amenities for Squirrel Island holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Squirrel Island

Sebasco Sprucewold Cabin@ the Beach
SUPERHOSTEntire cabin
Sebasco Sprucewold Cabin@ the Beach
Price:£88 / night
"Best of Maine" Oceanfront  Cottage 5 STARS
SUPERHOSTEntire guest house
"Best of Maine" Oceanfront Cottage 5 STARS
Price:£115 / night
Custom Built Quaint Knotty Pine Cottage
SUPERHOSTEntire cottage
Custom Built Quaint Knotty Pine Cottage
Price:£106 / night
3BR Vintage Cabin in Sprucewold — Newly Renovated!
Entire cabin
3BR Vintage Cabin in Sprucewold — Newly Renovated!
Price:£154 / night
Oceanfront contemporary home with stunning island and lighthouse views
Entire house
Oceanfront contemporary home with stunning island and lighthouse views
Price:£249 / night
The Rowe House
SUPERHOSTEntire house
The Rowe House
Price:£153 / night
Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!
Entire cabin
Inviting & rustic cabin w/wood-burning fireplace & grill- Enjoy a private beach!
Price:£118 / night
Water Views, Wrap Around Porch, 3 BR Coastal Home
Entire cottage
Water Views, Wrap Around Porch, 3 BR Coastal Home
Price:£248 / night
Ocean Peek Cottage
Entire cottage
Ocean Peek Cottage
Price:£135 / night
1920's cottage on the Maine Coast
Entire cabin
1920's cottage on the Maine Coast
Price:£111 / night
The Wharf Cottage at Harborfields on the Shore
Entire cottage
The Wharf Cottage at Harborfields on the Shore
Price:£137 / night
Chic Boothbay Harbor Studio Cabin
Entire bungalow
Chic Boothbay Harbor Studio Cabin
Price:£92 / night
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