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Squirrel Island Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Squirrel Island holiday rentals

A patio with a round glass table and two chairs, overlooking a grassy area with trees.

1. Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
8.0 out of 10, Very good, (13 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is HK$1,023
HK$1,569 total
includes taxes & fees
13 Sept - 14 Sept
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
A garden with hydrangea flowers, a wooden chair, and a "NO PARKING" sign.

2. Boothbay Harbor, 2-Story Cottage, downtown

Boothbay Harbor, 2-Story Cottage, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed the place, great location. "
United States
Erik P.
The price is HK$1,561
HK$3,009 total
includes taxes & fees
2 Oct - 3 Oct
Boothbay Harbor, 2-Story Cottage, downtown
A modern kitchen with a central island, stainless steel appliances, and a window providing natural light.

3. Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (37 reviews)
"Close enough to BoothBay Harbour and Botanical Gardens but private and quiet get away. Very comfortable! Spacious, good appliances and bedding. I would guess very new. Loved it!"
United States
Judith
The price is HK$1,899
HK$4,266 total
includes taxes & fees
13 Sept - 14 Sept
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

4. Holland Room 2 | Lighthouse View + Ocean Deck

Holland Room 2 | Lighthouse View + Ocean Deck
Boothbay Harbor
The price is HK$2,792
HK$3,361 total
includes taxes & fees
23 Sept - 24 Sept
Holland Room 2 | Lighthouse View + Ocean Deck
A modern kitchen with dark cabinets, a central island with bar stools, and a dining area with a round table and chairs.

5. Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
East Boothbay
10.0 out of 10, Exceptional, (62 reviews)
"Cute place with lots of ambiance. Close to Bay and Coastal Botanical Gardens. Very quiet and clean."
United States
Elaine G.
The price is HK$1,899
HK$4,317 total
includes taxes & fees
14 Sept - 15 Sept
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

6. Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Really lovely cabin with all the amenities within a stone’s throw to amazing trails and beaches. Would love to come back!"
United States
Palmer M.
The price is HK$1,779
HK$3,264 total
includes taxes & fees
30 Sept - 1 Oct
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A fenced garden area with a wooden gate, surrounded by greenery and trees.

7. Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Boothbay
6.0 out of 10, (5 reviews)
"It had a very homey feel, was nice to stay at for the night and wasn’t far from town."
United States
Audreyana P.
The price is HK$1,059
HK$1,615 total
includes taxes & fees
13 Sept - 14 Sept
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
A wooden staircase leading to a stone entrance of a building surrounded by trees.

8. Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
The price is HK$1,231
HK$4,026 total
includes taxes & fees
15 Sept - 16 Sept
Fully Renovated "Saltbox" Home in Boothbay
A treehouse with a wooden staircase and a small building with a colorful mural.

9. Perfect stopover, getaway & base to explore the Midcoast, or just chill in town.

Perfect stopover, getaway & base to explore the Midcoast, or just chill in town.
Bath
8.2 out of 10, Very good, (29 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is HK$819
HK$1,321 total
includes taxes & fees
13 Sept - 14 Sept
Perfect stopover, getaway & base to explore the Midcoast, or just chill in town.
A narrow hallway with a window on the right, leading to a room with a visible door.

10. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
10.0 out of 10, Exceptional, (11 reviews)
"Great location! We spent very little time in the room, but it was a great place to come back and crash! "
United States
Kristina M.
The price is HK$831
HK$1,812 total
includes taxes & fees
14 Sept - 15 Sept
Modern style in historic building in downtown Bath
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

11. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.6 out of 10, Excellent, (9 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
The price is HK$1,215
HK$1,812 total
includes taxes & fees
20 Sept - 21 Sept
Newly Renovated Cozy Cove Cabin at White Anchor Inn
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

12. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is HK$910
HK$1,907 total
includes taxes & fees
14 Sept - 15 Sept
Spacious 1 Bedroom Cottage Close to Everything 5
A wooden staircase with a wooden railing, surrounded by green foliage.

13. Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.

Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Bath
8.0 out of 10, Very good, (19 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is HK$847
HK$1,351 total
includes taxes & fees
13 Sept - 14 Sept
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
A wooden deck with a glass door leading to a room.

14. Tiny Cottage Near Everything 10

Tiny Cottage Near Everything 10
Edgecomb
8.6 out of 10, Excellent, (4 reviews)
"We recently stayed at the Tiny Cottage in Edgecomb, Maine, and truly enjoyed our visit. Except for a small initial issue, which was promptly and professionally addressed, everything was wonderful. The location is perfect for exploring the area, and the cottage itself was spotless, comfortable, and well-maintained. A lovely and relaxing getaway spot!"
United States
Elaine
The price is HK$737
HK$1,636 total
includes taxes & fees
14 Sept - 15 Sept
Tiny Cottage Near Everything 10
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

15. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate, very cute - “tiny cottage”We loved it!"
United States
Daniel B.
The price is HK$871
HK$1,950 total
includes taxes & fees
15 Sept - 16 Sept
Cheerful Cottage with Loft 9
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

16. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (50 reviews)
"Host communication was excellent. Location was ideal, walkable to the Boothbay Harbor attractions. Nice new wooden floors upstairs with the bedrooms. No AC which was fine for our stay. We must have stayed the first of the season, as the negatives were related to this. The toilets were disgusting with a foul odor and green mold on toilet seats, presumably from 9 months of zero use and the maids not cleaning prior to our arrival. Either way they should be replaced. All else with home was fine."
United States
Timothy M.
The price is HK$2,980
HK$5,830 total
includes taxes & fees
14 Sept - 15 Sept
Boothbay Harbor, The Francis Greene House, downtown
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

17. Harold Room 8 | 2 Queens + Gable Windows

Harold Room 8 | 2 Queens + Gable Windows
Boothbay Harbor
The price is HK$2,792
HK$3,498 total
includes taxes & fees
7 Oct - 8 Oct
Harold Room 8 | 2 Queens + Gable Windows
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

18. Renovated The Driftwood Cabin at White Anchor Inn

Renovated The Driftwood Cabin at White Anchor Inn
Boothbay
8.8 out of 10, Excellent, (3 reviews)
"Communication with Property Owner was excellent. This cute little cottage has been renovated and has a nice feel indoors. There is a beautiful porch on the back with a lovely view. The unit includes a mini fridge and mini microwave along with a little table and two chairs. If you have long hair, water pressure could be a concern. My shower worked great but the sink water pressure was not strong. The bed was comfortable and the decor was nice. The air conditioning works fine."
United States
Abra H.
The price is HK$1,372
HK$2,051 total
includes taxes & fees
18 Sept - 19 Sept
Renovated The Driftwood Cabin at White Anchor Inn
A small cabin with a wooden deck, surrounded by trees in a wooded area.

19. Spacious 1 Bedroom Cottage Close to Everything 3

Spacious 1 Bedroom Cottage Close to Everything 3
Edgecomb
9.6 out of 10, Exceptional, (18 reviews)
"Great central location"
United States
Bruce O.
The price is HK$1,161
HK$2,207 total
includes taxes & fees
14 Sept - 15 Sept
Spacious 1 Bedroom Cottage Close to Everything 3
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

20. Little Spruce Cottage | Wood Stove + Porch

Little Spruce Cottage | Wood Stove + Porch
Boothbay Harbor
The price is HK$4,752
HK$5,994 total
includes taxes & fees
16 Sept - 17 Sept
Little Spruce Cottage | Wood Stove + Porch
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Squirrel Island Hotel Reviews

Days Inn by Wyndham Brunswick Bath Area

Days Inn by Wyndham Brunswick Bath Area

8/10 Good
"Rooms were clean"
Kelly 1-night trip
Posted 4 hours ago
Days Inn by Wyndham Brunswick Bath Area

Find out more about Squirrel Island

Search for holiday rentals in Squirrel Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Squirrel Island using one of the methods below:

  • View our selection of featured holiday rentals in Squirrel Island
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  • Enter your travel dates to view the best deals on holiday rentals in Squirrel Island while they last

Look no further and take a look at our great range of rental properties in Squirrel Island!

Frequently asked questions

Can I find holiday rentals in Squirrel Island?

Yes, there are holiday rentals close to the most popular sights in Squirrel Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Squirrel Island has to offer?

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Squirrel Island is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Squirrel Island?

Explore the area and family-friendly sights such as Maine Maritime Museum, or get out into nature at a spot like Linekin Bay. Cabbage Island and Boothbay Harbor Marina are a couple of places you'll find in the wider area.

What are holiday rentals like in Squirrel Island?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Squirrel Island. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.