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Squirrel Island Holiday Rentals

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Our top choices for Squirrel Island holiday rentals

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, (11 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is NZ$276
includes taxes & fees
1 Sept - 2 Sept
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything

2. 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, (35 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 NZ$922
includes taxes & fees
5 Sept - 6 Sept
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor

3. 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, (60 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 NZ$922
includes taxes & fees
1 Sept - 2 Sept
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor

4. 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 NZ$343
includes taxes & fees
1 Sept - 2 Sept
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy

5. 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.
Boothbay Harbor, 2-Story Cottage, downtown

6. Holland Room 2 | Lighthouse View + Ocean Deck

Holland Room 2 | Lighthouse View + Ocean Deck
Boothbay Harbor
Holland Room 2 | Lighthouse View + Ocean Deck

7. 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 NZ$396
includes taxes & fees
2 Sept - 3 Sept
Modern style in historic building in downtown Bath

8. Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
The price is NZ$947
includes taxes & fees
31 Aug - 1 Sept
Fully Renovated "Saltbox" Home in Boothbay

9. Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.

Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.
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 NZ$302
includes taxes & fees
31 Aug - 1 Sept
Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.

10. 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 NZ$670
includes taxes & fees
29 Sept - 30 Sept
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC

11. Spacious 1 Bedroom Cottage Close to Everything 5

Spacious 1 Bedroom Cottage Close to Everything 5
Edgecomb
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful, clean, small cottage close to the coast, shopping and dining."
United States
Theresa
The price is NZ$433
includes taxes & fees
1 Sept - 2 Sept
Spacious 1 Bedroom Cottage Close to Everything 5

12. 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 NZ$383
includes taxes & fees
5 Sept - 6 Sept
Newly Renovated Cozy Cove Cabin at White Anchor Inn

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, (18 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is NZ$291
includes taxes & fees
31 Aug - 1 Sept
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.

14. Happy Cottage Near Everything 11

Happy Cottage Near Everything 11
Edgecomb
6.8 out of 10, (3 reviews)
"Great quit little place, great accommodations with even better help and information about the local area."
United States
George
The price is NZ$339
includes taxes & fees
28 Sept - 29 Sept
Happy Cottage Near Everything 11

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 NZ$433
includes taxes & fees
8 Sept - 9 Sept
Cheerful Cottage with Loft 9

16. Boothbay Harbor, The Francis Greene House, downtown

Boothbay Harbor, The Francis Greene House, downtown
Boothbay Harbor
9.4 out of 10, Exceptional, (48 reviews)
"We spent three nights at this location, which is just a short walk from the commercial area of Boothbay Harbor. In addition to restaurants in town it is only minutes away from Robinson's Wharf, which had some of the best food we experienced in 14 days of travel - definitely the best lobster. The house was as advertised and suited our needs well."
United States
Terry F.
The price is NZ$1,194
includes taxes & fees
5 Sept - 6 Sept
Boothbay Harbor, The Francis Greene House, downtown

17. 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)
The price is NZ$439
includes taxes & fees
5 Sept - 6 Sept
Renovated The Driftwood Cabin at White Anchor Inn

18. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (68 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is NZ$489
includes taxes & fees
2 Sept - 3 Sept
A Spacious Vacation Cottage in Sheepscot Harbour

19. Oriole Suite | Stone Fireplace + Woodland

Oriole Suite | Stone Fireplace + Woodland
Boothbay Harbor
The price is NZ$1,272
includes taxes & fees
7 Sept - 8 Sept
Oriole Suite | Stone Fireplace + Woodland

20. Pond Cabin: Private Sauna+Near Beach+FirePit+Pond

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is NZ$945
includes taxes & fees
8 Sept - 9 Sept
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
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

Find out more about Squirrel Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Squirrel Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Squirrel Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Squirrel Island. Seeing all the best attractions is bound to make you fall in love with Squirrel Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Squirrel Island short-term rentals, that won’t be hard to do.

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 Grimes Cove Beach. Linekin Bay and Cabbage Island 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.