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Squirrel Island Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

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. 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 AU$322
includes taxes & fees
30 Aug - 31 Aug
Newly Renovated Cozy Cove Cabin at White Anchor Inn
A fenced garden area with a wooden gate, surrounded by greenery and trees.

2. 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 AU$274
includes taxes & fees
20 Aug - 21 Aug
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

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

Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Boothbay
7.8 out of 10, Good, (10 reviews)
"Great stay! Pet friendly, super responsive host and excellent location!"
United States
Cassie M.
The price is AU$281
includes taxes & fees
1 Sept - 2 Sept
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
A modern kitchen with a central island, stainless steel appliances, and a window providing natural light.

4. 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, (34 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 AU$818
includes taxes & fees
5 Sept - 6 Sept
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
A garden with hydrangea flowers, a wooden chair, and a "NO PARKING" sign.

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.
The price is AU$586
includes taxes & fees
27 Aug - 28 Aug
Boothbay Harbor, 2-Story Cottage, downtown
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

6. 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 AU$342
includes taxes & fees
26 Aug - 27 Aug
Renovated The Driftwood Cabin at White Anchor Inn
A narrow hallway with a window on the right, leading to a room with a visible door.

7. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (10 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 AU$314
includes taxes & fees
1 Sept - 2 Sept
Modern style in historic building in downtown Bath
A circular pool with lounge chairs and umbrellas, surrounded by a rocky shoreline and a pier extending into the water.

8. Harold Room 8 | 2 Queens + Gable Windows

Harold Room 8 | 2 Queens + Gable Windows
Boothbay Harbor
The price is AU$652
includes taxes & fees
30 Aug - 31 Aug
Harold Room 8 | 2 Queens + Gable Windows
A treehouse with a wooden staircase and a small building with a colorful mural.

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

Captain's Guest Room. Authenticity. Great Value. Walk to everything.
Bath
8.4 out of 10, Very good, (27 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 AU$255
includes taxes & fees
30 Aug - 31 Aug
Captain's Guest Room. Authenticity. Great Value. Walk to everything.
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

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 AU$630
includes taxes & fees
16 Sept - 17 Sept
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A modern kitchen with dark cabinets, a central island with bar stools, and a dining area with a round table and chairs.

11. 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, (58 reviews)
"Excellent, clean property. "
United States
Andy H.
The price is AU$859
includes taxes & fees
20 Aug - 21 Aug
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
A deck with a table and chairs, overlooking a wooded area with trees and a house in the background.

12. 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 AU$305
includes taxes & fees
15 Sept - 16 Sept
Happy Cottage Near Everything 11
A kitchen with a large island, two bar stools, wooden cabinets, a red refrigerator, and a view of the outdoors through large windows.

13. 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 AU$386
includes taxes & fees
15 Sept - 16 Sept
Spacious 1 Bedroom Cottage Close to Everything 5
A two-story house with a covered porch, a garage, and a front yard with potted plants.

14. Large suite/private bath/private entrance on quiet street near Thomas Bay

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (163 reviews)
"Susan and Jeff were amazing hosts! There were so kind, thoughtful and welcoming. The suite was extremely spacious, well decorated and very comfortable. We were very close to the Air Show which was the reason for our trip. They gave us great instructions for a short cut to the airfield and amazing dinner recommendations. We could not have chosen a better place to stay. We highly recommend this place!"
United States
Asha
The price is AU$232
includes taxes & fees
2 Sept - 3 Sept
Large suite/private bath/private entrance on quiet street near Thomas Bay
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 AU$369
includes taxes & fees
25 Aug - 26 Aug
Cheerful Cottage with Loft 9
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

16. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (67 reviews)
"Great place and great restaurants."
United States
Julie D.
The price is AU$432
includes taxes & fees
2 Sept - 3 Sept
A Spacious Vacation Cottage in Sheepscot Harbour
A cabin with a large wooden barrel-shaped structure attached to the main building, featuring a warm interior light.

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
The price is AU$738
includes taxes & fees
8 Sept - 9 Sept
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
A wooden staircase with a wooden railing, surrounded by green foliage.

18. Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.

Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
Bath
8.0 out of 10, Very good, (17 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is AU$238
includes taxes & fees
30 Aug - 31 Aug
Captain's 1BR Apt. Experience authentic Maine. Near everything. No fees.
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

19. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.6 out of 10, Exceptional, (7 reviews)
"Second time we have stay in this cottage. The perfect location for a Maine vacation. "
United States
chuck c.
The price is AU$400
includes taxes & fees
13 Sept - 14 Sept
Mid Coast Getaway w/ water views
Two Adirondack chairs facing a body of water with a bridge in the background.

20. Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River

Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
Edgecomb
9.8 out of 10, Exceptional, (86 reviews)
"The cottage was perfect for our stay. The location is great for visiting all the sights, shopping, and dining in the area. But, we could have just stayed at the cottage, relaxed, and Bern perfectly happy. "
United States
Ann M.
The price is AU$441
includes taxes & fees
6 Sept - 7 Sept
Spectacular Waterfront Cottage: Charming Getaway on The Sheepscot River
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

Topside Inn

Topside Inn

10/10 Excellent
"Our stay was excellent! We enjoyed our balcony view from our comfortable patio chairs. Breakfast was top notch. All in all, we will return!"
Maurice 1-night trip
Posted 1 hour ago
Topside Inn

Find out more about Squirrel Island

Everything you need to know about Squirrel Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Squirrel Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Squirrel Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Squirrel Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Squirrel Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Squirrel Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Squirrel Island holiday rentals we have selected for you start as low as AU$255 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Squirrel Island rentals

At Expedia, we put the best Squirrel Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Squirrel Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Squirrel Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Squirrel Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.