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Squirrel Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Squirrel Island vacation rentals

Terrace/patio

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.
$150 nightly
The price is $163
Sep 1 - Sep 2
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Private kitchen

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
$504 nightly
The price is $549
Sep 5 - Sep 6
Total with taxes and fees
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
Private kitchen

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.
$505 nightly
The price is $551
Sep 1 - Sep 2
Total with taxes and fees
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
Property grounds

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.
$189 nightly
The price is $206
Sep 1 - Sep 2
Total with taxes and fees
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
Property grounds

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
Pool

6. Holland Room 2 | Lighthouse View + Ocean Deck

Holland Room 2 | Lighthouse View + Ocean Deck
Boothbay Harbor
$481 nightly
The price is $524
Sep 23 - Sep 24
Total with taxes and fees
Holland Room 2 | Lighthouse View + Ocean Deck
Interior

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.
$217 nightly
The price is $237
Sep 1 - Sep 2
Total with taxes and fees
Modern style in historic building in downtown Bath
Property grounds

8. Fully Renovated "Saltbox" Home in Boothbay

Fully Renovated "Saltbox" Home in Boothbay
Boothbay
$520 nightly
The price is $567
Aug 31 - Sep 1
Total with taxes and fees
Fully Renovated "Saltbox" Home in Boothbay
Outdoor dining

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
$145 nightly
The price is $158
Sep 2 - Sep 3
Total with taxes and fees
Captain's Guest Room. Authenticity. Great Value. Large yard. Walk to everything.
Room

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.
$381 nightly
The price is $405
Sep 29 - Sep 30
Total with taxes and fees
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
Private kitchen

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
$245 nightly
The price is $259
Aug 31 - Sep 1
Total with taxes and fees
Spacious 1 Bedroom Cottage Close to Everything 5
Terrace/patio

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.
$211 nightly
The price is $230
Sep 6 - Sep 7
Total with taxes and fees
Newly Renovated Cozy Cove Cabin at White Anchor Inn
Property grounds

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
$158 nightly
The price is $172
Aug 31 - Sep 1
Total with taxes and fees
Captain's 1BR Suite. Authenticity. Value. Walk to everything. Large yard.
Outdoor dining

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
$205 nightly
The price is $207
Sep 28 - Sep 29
Total with taxes and fees
Happy Cottage Near Everything 11
Room

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.
$245 nightly
The price is $259
Sep 7 - Sep 8
Total with taxes and fees
Cheerful Cottage with Loft 9
Private kitchen

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.
$661 nightly
The price is $720
Sep 5 - Sep 6
Total with taxes and fees
Boothbay Harbor, The Francis Greene House, downtown
Terrace/patio

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)
"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.
$240 nightly
The price is $262
Sep 6 - Sep 7
Total with taxes and fees
Renovated The Driftwood Cabin at White Anchor Inn
Living area

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.
$268 nightly
The price is $292
Sep 2 - Sep 3
Total with taxes and fees
A Spacious Vacation Cottage in Sheepscot Harbour
Pool

19. Oriole Suite | Stone Fireplace + Woodland

Oriole Suite | Stone Fireplace + Woodland
Boothbay Harbor
$720 nightly
The price is $785
Sep 7 - Sep 8
Total with taxes and fees
Oriole Suite | Stone Fireplace + Woodland
Property grounds

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
$530 nightly
The price is $567
Sep 8 - Sep 9
Total with taxes and fees
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

The Federal

The Federal

8/10 Good
"Breakfast would be nice."
Tina 1-night trip
Posted 2 hours ago
The Federal

Find out more about Squirrel Island

Everything you need to know about Squirrel Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Squirrel Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Squirrel Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Squirrel Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $158 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Squirrel Island rentals

At Expedia, we put the best Squirrel Island vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Squirrel Island?

Yes, we have vacation rentals close to the most popular local attractions in Squirrel Island, or you can go with a more secluded option if you want a relaxing place to stay.

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

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This vacation home rental near Squirrel Island is located on the beach and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 larger area.

What are vacation rentals like in Squirrel Island?

Vacation rentals are private properties you can book for a couple of days or more in Squirrel Island. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for families.