Squirrel Island Holiday Rentals, Maine: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Squirrel Island

Pet friendly

Apartment

Pool

Condo

Cottage

Family friendly

Waterpark

Cabin

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Squirrel Island hotels

An aerial view of a coastal property with a large house, a circular driveway, and a view of the ocean.

A restaurant with wooden tables and chairs, two plates of seafood, and wine glasses.

A coastal marina with boats, a small dock, and a grassy area.

A deck with wooden chairs and a table, overlooking a grassy area with trees and a body of water.

1. Newagen Seaside Inn

Southport

elizabeth brian

฿6,173

฿7,631 total

includes taxes & fees

27 Sept - 28 Sept

A dining area with tables set for two, large windows offering a view of a sunset over a body of water, and wooden chairs with cushioned seats.

A two-story house with a balcony, large windows, and a view of the water.

A swimming pool area at night with a clear view of the stars, a dock, and a small shed.

A cozy living room with a fireplace, two armchairs, a coffee table, and lamps.

2. Spruce Point Inn

Boothbay Harbor

Andrew

฿7,010

฿8,787 total

includes taxes & fees

28 Sept - 29 Sept

A lakeside lodge with multiple buildings, docked boats, and a forested shoreline.

3. Ocean Gate Inn

Southport

COLLEEN

฿9,274

฿10,614 total

includes taxes & fees

24 Sept - 25 Sept

A dining area with a table and chairs, large windows with a view of the water, and a wooden ceiling.

A waterfront restaurant with outdoor seating, a dock, and a view of the water.

A dining area with a view of the water, a table with chairs, and a window with blinds.

A wooden table with a clear glass vase and pampas grass, overlooking a lakeside view with outdoor seating and umbrellas.

4. Bluebird Ocean Point Inn

Ocean Point

James

฿7,096

฿8,456 total

includes taxes & fees

30 Sept - 1 Oct

A covered porch with hanging flower baskets and outdoor seating.

A cozy living room with a fireplace, a dining table set with food, and comfortable seating.

A bedroom with a bed, two windows with shutters, a lamp, a chair, and a wall-mounted light fixture.

A dining table with a cake, cookies, and a vase of flowers.

5. Five Gables Inn

East Boothbay

Mark

฿7,287

฿7,942 total

includes taxes & fees

24 Sept - 25 Sept

A lakeside deck with seating and a covered area, overlooking a body of water and a forested area.

A pool area with a view of the water, lounge chairs, and flags.

A dock with kayaks and a building with a deck overlooking the water.

A waterfront property with a pool, outdoor seating, and a flagpole with multiple flags.

6. Linekin Bay Resort

Boothbay Harbor

William

฿8,173

฿9,799 total

includes taxes & fees

13 Oct - 14 Oct

A waterfront dining area with a fire feature, boats, and a sunset view.

A waterfront view with three Adirondack chairs facing a marina with boats docked.

A waterfront town with a pier, boats, and houses along the river.

A waterfront hotel with a white exterior, multiple balconies with red flower boxes, and a clear view of the water.

7. Boothbay Harbor Inn

Boothbay Harbor

Roy

฿6,293

฿6,859 total

includes taxes & fees

24 Sept - 25 Sept

A bedroom with a large bed, white walls, wooden ceiling, and a view of the water.

A room with a wooden parquet floor, white wainscoting, large windows with a view, and a glass table with chairs.

A bright, well-lit room with a glass table, a tufted sofa, patterned armchairs, and large windows offering a view of the outdoors.

A waterfront property with a large house featuring a front porch, a driveway, and a lawn.

8. Topside Inn

Boothbay Harbor

Dan

฿9,324

฿10,163 total

includes taxes & fees

20 Oct - 21 Oct

A waterfront property with a dock, a boat, and a multi-story building with balconies.

A room with two blue armchairs, a small wooden table, and a TV on the wall.

A waterfront patio with wicker furniture, a red umbrella, and a view of boats and a pier.

A harbor with a sailboat, buildings, and a church.

9. Tugboat Inn

Boothbay Harbor

Deborah

฿6,624

฿7,220 total

includes taxes & fees

18 Oct - 19 Oct

A wooden bridge leading to a building with a sign that reads "CAROUSEL MUSIC THEATER".

A buffet setup with various food items and beverages, including a fruit bowl, yogurt containers, and a juice dispenser.

A hotel room with two beds, a TV, a microwave, a coffee maker, and a chair.

The exterior of Flagship Inn with a prominent sign, a large window, and a blue awning.

10. Flagship Inn and Suites

Boothbay Harbor

Jean

฿3,941

฿5,599 total

includes taxes & fees

1 Oct - 2 Oct

A stone fire pit surrounded by chairs, a stone wall, and a windowed area with a bench.

An indoor swimming pool with clear glass walls, green chairs, and a tiled floor.

A spacious hotel lobby with a fireplace, seating area, and a reception desk.

A reception area with two curved reception desks, a tiled floor, and a patterned wall.

11. Residence Inn Bath Brunswick Area

Bath

Ted

฿4,476

฿4,879 total

includes taxes & fees

18 Oct - 19 Oct

A street lamp and a stone sculpture on a pedestal.

A large bed with white linens, wooden headboard, two bedside tables with lamps, and two framed pictures on the wall.

A building with a sign indicating an office and vacancy. There are white chairs outside.

A bathroom with a white sink, toilet, and a hairdryer on the wall.

12. Mid-Town Motel

Boothbay Harbor

Susan

฿5,634

฿6,638 total

includes taxes & fees

27 Sept - 28 Sept

A balcony with two wooden chairs and a small table, overlooking a body of water with houses in the background.

A marina with various boats docked and a pier extending into the water.

A bedroom with a large bed, a view of a lake, and a row of houses in the background.

A modern kitchen with a wooden panel wall, a built-in TV, and a dining area with patterned chairs.

13. Harborage Inn on the Oceanfront

Boothbay Harbor

Abeer

฿10,906

฿11,887 total

includes taxes & fees

13 Oct - 14 Oct

A wooden deck with white chairs overlooking a marina with boats.

A marina with boats docked, a flagpole with an American flag, and a building with a blue roof.

An aerial view of a coastal town with a marina, boats, and a bridge connecting to a peninsula.

A room with two blue armchairs, a small wooden table, and large windows offering a marina view.

14. Fishermans Wharf Inn

Boothbay Harbor

JAMES

฿6,293

฿6,859 total

includes taxes & fees

1 Oct - 2 Oct

A wooden deck with a table and chairs, overlooking a marina with boats and houses.

A room with a wooden ceiling, large windows with blinds, a grey sofa, a beige armchair, and a patterned rug.

A room with large windows, wooden chairs, a green sofa, and a patterned rug.

15. Greenleaf Inn

Boothbay Harbor

Christine

฿7,703

฿8,923 total

includes taxes & fees

24 Sept - 25 Sept

A lobby with a fireplace, seating area, and a welcome sign.

A reception desk with a "Welcome to the Lobster State" sign, a phone, and a "Hilton Honors" badge.

A hotel lobby with a sofa, chairs, a TV, and a dining area.

A gym with exercise equipment, a mirror, and a rack of dumbbells.

16. Hampton Inn Bath (Brunswick Area)

Bath

Robert

฿5,405

฿5,891 total

includes taxes & fees

20 Oct - 21 Oct

A hotel room with two beds, a nightstand, a lamp, and a chair.

A brick building with a central entrance labeled "OFFICE," flanked by windows and a small tree.

A hotel lobby with a reception desk, two patterned armchairs, a small table with a vase of flowers, and wall art.

17. Days Inn by Wyndham Brunswick Bath Area

Brunswick

Michel E

฿3,809

฿4,152 total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with a bed, a desk, a chair, a television, and a picture on the wall.

A room with a grey wall, wooden floor, a grey sofa, a wooden dresser, and white-framed windows with blinds.

A compact kitchenette with a microwave, coffee maker, and a small trash bin.

A two-level bunk bed with purple bedding, white headboard, and a white radiator on the wall.

18. The Thistle Inn

Boothbay Harbor

Gary

฿5,932

฿6,466 total

includes taxes & fees

24 Sept - 25 Sept

A hotel with a large driveway, well-maintained lawn, and a sign indicating the name.

A hotel room with a bed, a desk, a television, a minibar, and a view of the outdoors.

A deck with wicker furniture overlooking a well-maintained lawn and a distant body of water.

19. Cod Cove Inn, BW Signature Collection

Edgecomb

ANNA

฿4,935

฿5,380 total

includes taxes & fees

18 Oct - 19 Oct

A room with a dining area, a large window with curtains, a radiator, and a potted plant.

A white two-story house with a balcony, surrounded by a garden with various plants and flowers.

20. Admirals Quarters Inn

Boothbay Harbor

Tracey

฿8,559

฿11,009 total

includes taxes & fees

18 Oct - 19 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Squirrel Island Hotel Reviews

Best Western Plus Brunswick Bath

8/10 Good

"Nicer than expected for a Best Western, pleasantly surprised. Good value."

Ocean Gate Inn

8/10 Good

"Lots of fun stufffor kids"

Hampton Inn Bath (Brunswick Area)

10/10 Excellent

"Front desk clerk in the morning was very personable and knowledgeable. Need more seating for groups larger than 3 in the lobby/breakfast area"

Boothbay Harbor Inn

10/10 Excellent

"Gorgeous property on the water, room was clean and spacious with a beautiful view, ed was super comfortable!"

Flagship Inn and Suites

8/10 Good

"It was a sufficient for what we needed."

Cod Cove Inn, BW Signature Collection

10/10 Excellent

"We enjoyed our one night stay on our way up the coast. The hotel was easy to find and was a convenient proximity to town. We had a comfortable bed and the facility was quiet so we could get a good night’s rest. We did not take advantage of any of the amenities so cannot comment on those, but would definitely stay again."

Tugboat Inn

10/10 Excellent

"Perfect location, great views"

Topside Inn

10/10 Excellent

"This property is fabulous and it's on top of a little hill which overlooks BoothBay. Totally renovated. Super cute inside. Has a small living room with a small bar for Happy Hour . Website said breakfast included. Well, I just the a continental...nope...they had a chef which cooked ills a fabulous breakfast. Award winning! Definitely would stay here again but ask for a room in the actual house. Our room was located in adjacent to the house which was still nice but probably nicier if you get to stay in the house. There are no elevators so you need to be able to carry your luggage up a flight. Excellent B&B"

Smuggler's Cove Inn

10/10 Excellent

"Great place. We were very pleased."

More cheap stays in Squirrel Island