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Squirrel Island Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Squirrel Island vacation rentals

A lakeside deck with a fire pit, docked boats, and a wooden railing.

1. Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law

Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
Boothbay Harbor
10.0 out of 10, Exceptional, (129 reviews)
"This place was the definition of relaxation! The access to West Harbor "Pond" (it's huge -- more like a lake!) was unbeatable! We were able to use the provided kayaks to explore the little islands in the water and to come really close to a pair of loons!"
United States
Melinda M.
$291 nightly
The price is $317
Nov 11 - Nov 12
Total with taxes and fees
Peaceful Lake waterfront! Full Kitchen! Ht&AC! Is Private entry waterside in-law
A modern kitchen with a central island, bar stools, and a dining area with a view of trees.

2. 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, (64 reviews)
"Tucked away in a wooded lot, quick drive to Boothbay Harbor. Side by side units are great for friends or families traveling together."
United States
Carly C.
$478 nightly
The price is $521
Nov 11 - Nov 12
Total with taxes and fees
Shipbuilder’s Retreat sleeps 6, 5 minutes to Harbor
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, (41 reviews)
"The property was quiet and beautiful. It had everything we needed for a three night stay."
United States
Jordana S.
$509 nightly
The price is $555
Nov 29 - Nov 30
Total with taxes and fees
Shipbuilder's Retreat, Unit 2, Sleeps 6, 5 minutes to Harbor
A small house with a porch, two chairs, and a picnic table.

4. Across the road from Pemaquid Beach: a wooded king-bed cabin for couples

Across the road from Pemaquid Beach: a wooded king-bed cabin for couples
Pemaquid Beach
10.0 out of 10, Exceptional, (22 reviews)
"The cabin was perfect; the location even better, and the hosts were everything you could wish for."
United States
Mia
$253 nightly
The price is $275
Dec 7 - Dec 8
Total with taxes and fees
Across the road from Pemaquid Beach: a wooded king-bed cabin for couples
A bedroom with a bed, a small table with a yellow mug, and a window with a view of a forest.

5. 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.
$347 nightly
The price is $367
Nov 11 - Nov 12
Total with taxes and fees
Spruce Studio: Near Beach+Private Sauna+FirePit+Pond+Heat/AC
A lakeside cabin with a deck overlooking the water, surrounded by trees.

6. 1920s Riverfront Cottage – Historic Maine Charm

1920s Riverfront Cottage – Historic Maine Charm
Edgecomb
9.6 out of 10, Exceptional, (5 reviews)
"This cottage is the perfect blend of historic charm and modern upgrades. The view of the river is incredible, and the secluded location is just a short drive from downtown Wiscasset and Edgecomb. The sunroom is already a great place to hang out and enjoy the river view, but the owners are also putting in a lot of work to create an enjoyable outdoor space. Jeffrey is easy to work with and honestly wants you to have a good stay."
United States
Shelly
$346 nightly
The price is $348
Nov 11 - Nov 12
Total with taxes and fees
1920s Riverfront Cottage – Historic Maine Charm
A patio with a round glass table and two chairs, overlooking a grassy area with trees.

7. Newly Renovated Cozy Cove Cabin at White Anchor Inn

Newly Renovated Cozy Cove Cabin at White Anchor Inn
Boothbay
8.0 out of 10, Very good, (11 reviews)
"As advertised, comfy bed cozy cabin. Would stay again "
United States
Joseph B.
$515 nightly
The price is $561
Nov 17 - Nov 18
Total with taxes and fees
Newly Renovated Cozy Cove Cabin at White Anchor Inn
A fenced garden area with a wooden gate, surrounded by greenery and trees.

8. 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.
$510 nightly
The price is $556
Nov 11 - Nov 12
Total with taxes and fees
Newly renovated motel garden rooms heart of boothbay affordable great hospitaliy
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

9. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.4 out of 10, Exceptional, (23 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
$270 nightly
The price is $271
Nov 11 - Nov 12
Total with taxes and fees
Fantastic Waterfront Views
A spacious living area with a wooden ceiling, a dining table with chairs, and a kitchen area with white cabinets.

10. 3 Bedroom Happy Cottage 15

3 Bedroom Happy Cottage 15
Edgecomb
10.0 out of 10, Exceptional, (14 reviews)
"A great property and easy process."
United States
Dan L.
$425 nightly
The price is $426
Nov 11 - Nov 12
Total with taxes and fees
3 Bedroom Happy Cottage 15
A deck with outdoor furniture, a table, and chairs, overlooking a body of water and buildings.

11. Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly

Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly
Boothbay Harbor
8.0 out of 10, Very good, (2 reviews)
"Ok Beautiful location price was on the high side but very clean and state of the art."
United States
Steve R.
$635 nightly
The price is $692
Nov 20 - Nov 21
Total with taxes and fees
Walk-to-Town Boothbay Harbor Retreat | Harbor Views | A/C | Parking| Pet Friendly
A cabin with a large wooden barrel-shaped structure attached to the main building, featuring a warm interior light.

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

Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
Georgetown
$433 nightly
The price is $461
Nov 15 - Nov 16
Total with taxes and fees
Pond Cabin: Private Sauna+Near Beach+FirePit+Pond
A spacious living room with a beige sectional sofa, a round coffee table, and a teal armchair. Large windows with white curtains allow natural light to fill the room.

13. Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920

Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920
Pemaquid Beach
10.0 out of 10, Exceptional, (11 reviews)
"Comfortable, clean and beautiful "
United States
Corina
$603 nightly
The price is $657
Nov 12 - Nov 13
Total with taxes and fees
Across the road from Pemaquid Beach: a 4-bedroom Maine home built in 1920
A narrow hallway with a window on the right, leading to a room with a visible door.

14. Modern style in historic building in downtown Bath

Modern style in historic building in downtown Bath
Bath
9.8 out of 10, Exceptional, (14 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.
$194 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Modern style in historic building in downtown Bath
A cozy living room with a wooden ceiling, a white sofa, a coffee table, and a dark armchair.

15. A Spacious Vacation Cottage in Sheepscot Harbour

A Spacious Vacation Cottage in Sheepscot Harbour
Edgecomb
10.0 out of 10, Exceptional, (72 reviews)
"Great place and great restaurants."
United States
Julie D.
$264 nightly
The price is $288
Nov 15 - Nov 16
Total with taxes and fees
A Spacious Vacation Cottage in Sheepscot Harbour
A modern kitchen with dark cabinetry, a stainless steel range, and a window with a view of greenery.

16. Award Winning Luxury Carriage House a short stroll from town!

Award Winning Luxury Carriage House a short stroll from town!
Bath
10.0 out of 10, Exceptional, (14 reviews)
"Another great stay by a great host. The host Jared even provided some activities for our granddaughters to do while we were on vacation. You will not be disappointed with this property. Looking to stay there again in the future. Thank you, Jared!"
United States
Ronald H.
$416 nightly
The price is $453
Nov 14 - Nov 15
Total with taxes and fees
Award Winning Luxury Carriage House a short stroll from town!
A two-story house with a covered porch, a garage, and a front yard with potted plants.

17. 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, (176 reviews)
"This is a really lovely place to stay. Clean and very comfortable with lovely hosts."
United Kingdom
Lucinda
$107 nightly
The price is $117
Dec 1 - Dec 2
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A backyard with a red Adirondack chair, a barbecue grill, and a wooden treehouse.

18. 1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!

1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
Bath
8.0 out of 10, Very good, (31 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
$163 nightly
The price is $178
Nov 24 - Nov 25
Total with taxes and fees
1BR + Bath. Private Entrance. Walk to everything, Large yard. Pets stay free!
A wooden cabin interior with a loft bedroom, a kitchen area, and a dining space.

19. Cheerful Cottage with Loft 9

Cheerful Cottage with Loft 9
Edgecomb
10.0 out of 10, Exceptional, (5 reviews)
"The cabin was clean and cozy! We enjoyed our stay."
United States
Caitlin R.
$184 nightly
The price is $192
Nov 11 - Nov 12
Total with taxes and fees
Cheerful Cottage with Loft 9
A bedroom with a large bed, a desk with two red chairs, a window with blinds, and a nightstand with a lamp.

20. Cheerful Cottage Close to Everything 12

Cheerful Cottage Close to Everything 12
Edgecomb
9.4 out of 10, Exceptional, (19 reviews)
"Cute place and very clean will definitely stay again "
United States
Tom C.
$187 nightly
The price is $195
Nov 12 - Nov 13
Total with taxes and fees
Cheerful Cottage Close to Everything 12
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

Mid-Town Motel

Mid-Town Motel

8/10 Good
"Very cute and clean, very nice staff"
Lauren 1-night trip
Posted 18 hours ago
Mid-Town Motel

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 $117 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.

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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 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. Cabbage Island and Burnt Island Living Lighthouse 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.