Squirrel Island Vacation Rentals

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Vacation Rentals in Squirrel Island

Interior
Last minute deal Ocean Point OCEANFRONT with private BEACH

Last minute deal Ocean Point OCEANFRONT with private BEACH

Boothbay
10.0 out of 10, Exceptional, (100)
"Had a great stay! Such a beautiful secluded spot, but also close to boothbay harbor and a lot of other Maine coast activities. The apartment itself was clean and nice and everything was smooth and easy. Would definitely stay here again!"
United States
Richard L.
Last minute deal Ocean Point OCEANFRONT with private BEACH
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island
10.0 out of 10, Exceptional, (234)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Outdoor dining
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.

Boothbay Harbor
10.0 out of 10, Exceptional, (20)
"We loved our stay in Boothbay. The cottage was clean and comfortable, location was ideal, easy walk into town and to the park. Everything was fantastic, would highly recommend. "
United States
Emma D.
Enjoy spectacular views of Lobster Cove. Large yard, EV charger & dog friendly.
Fridge, microwave, oven, stovetop
1 room luxury ocean front studio cottage

1 room luxury ocean front studio cottage

Harpswell
9.6 out of 10, Exceptional, (170)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Property grounds
Captain's Guest Room w/private bath. Walk to everything.

Captain's Guest Room w/private bath. Walk to everything.

Bath
8.2 out of 10, Very Good, (21)
"Great location and a beautiful property. Great walking/driving distance from town and the waterfront, we had a great stay and would do it again! "
United States
Nina P.
Captain's Guest Room w/private bath. Walk to everything.
Interior
Oceanfront Cabin-Castle in Maine Woods

Oceanfront Cabin-Castle in Maine Woods

Georgetown
9.8 out of 10, Exceptional, (43)
"Amazing views and good location "
United States
Adriana R.
Oceanfront Cabin-Castle in Maine Woods
Terrace/patio
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, (7)
"Affordable and quiet location that felt safe and is conveniently close to Boothbay Harbor & surrounding attractions. "
United States
Melanie L.
$184 nightly
The price is $200
Dec 2 - Dec 3
Total with taxes and fees
Cozy Renovated Cabin in Central Boothbay– Peaceful, Private, Close to Everything
Exterior
Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell
9.4 out of 10, Exceptional, (23)
"We loved our stay! Gorgeous view, lots of thoughtful little amenities. The home was extremely clean and the host was just lovely. "
United States
Catherine O.
Beautiful Oceanfront House- Stunning Water Views
Outdoor dining
Maine Coast House with Spectacular Ocean Views and Beach for Swimming

Maine Coast House with Spectacular Ocean Views and Beach for Swimming

South Bristol
9.4 out of 10, Exceptional, (27)
"Perfect base for exploring the mid-coast region. "
United States
Rebecca M.
$440 nightly
The price is $480
Dec 2 - Dec 3
Total with taxes and fees
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
Fridge, microwave, oven, stovetop
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views

Boothbay Harbor
9.2 out of 10, Wonderful, (100)
"Great views from backyard and living room. Others have described the place as rustic, which is fair as regards wood flooring, paneling and rugs. But beds, sofas and chairs are very comfortable. Heating wasn’t working on the second floor, but they sent someone to look at it almost immediately. Although they couldn’t fix it during our stay, they gave us a fair partial refund."
United States
Daniel
Downtown Waterfront Cottage on the Shore of Mill Cove w/ Lovely Views
Property grounds
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C

Boothbay Harbor
10.0 out of 10, Exceptional, (104)
"Lovely home and perfect location"
United States
Sara A.
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Pool
Quintessential Maine Oceanfront home

Quintessential Maine Oceanfront home

Bremen
10.0 out of 10, Exceptional, (79)
"Great place room for everyone. Hot tub was great. Lots of outdoor space and activities."
United States
Lucie F.
Quintessential Maine Oceanfront home
TV, fireplace
Peaceful home with forest views & great yard - minutes to town

Peaceful home with forest views & great yard - minutes to town

Wiscasset
7.8 out of 10, Good, (9)
"Fit our needs perfectly!"
United States
Aimee K.
Peaceful home with forest views & great yard - minutes to town
Exterior
Wiggleswick Cottage; A Dogs Welcome Certified Property! 11/28-12/1 availability!

Wiggleswick Cottage; A Dogs Welcome Certified Property! 11/28-12/1 availability!

Georgetown
10.0 out of 10, Exceptional, (58)
"Our first time to Maine was one to remember. Every detail was well thought out and the communication before, during, and after was amazing. Hope to come back one day!"
United States
Seth L.
Wiggleswick Cottage; A Dogs Welcome Certified Property! 11/28-12/1 availability!
Fridge, microwave, oven, stovetop
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Boothbay Harbor
10.0 out of 10, Exceptional, (90)
"This was our third year staying. Perfect location! "
United States
Debra G.
Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.
Fridge, microwave, oven, stovetop
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay

Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay

Boothbay Harbor
9.6 out of 10, Exceptional, (44)
"The location (we walked to all shops and eateries at the harbor), amenities, and comfort we're exceptional."
United States
Katharine P.
Dog-friendly home with deck, pool table, & firepit - walk to downtown Boothbay
Smart TV
Shipwright @ The Offshore House

Shipwright @ The Offshore House

Boothbay
9.4 out of 10, Exceptional, (13)
"Great location. Easy location to town and Dunkin Donuts accros street. "
United States
Steven
$284 nightly
The price is $301
Dec 2 - Dec 3
Total with taxes and fees
Shipwright @ The Offshore House
Interior
Popham Beach Direct Oceanfront Cottage Steps to the sand

Popham Beach Direct Oceanfront Cottage Steps to the sand

Phippsburg
9.8 out of 10, Exceptional, (69)
"So relaxing!! "
United States
Christina G.
Popham Beach Direct Oceanfront Cottage Steps to the sand
TV, fireplace
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces

Westport
8.4 out of 10, Very Good, (49)
"This home was absolutely stunning! Beautiful inside, amazing view of the water. I loved sitting out on the porch so much. I would highly recommend!"
United States
Brian Q.
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Terrace/patio
Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier

Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier

Boothbay Harbor
10.0 out of 10, Exceptional, (2)
"This location was very convenient for tour boat trips, restaurants and shopping. There are high end appliances and lighting, and the interior is furnished in a rustic dog-themed way. There is a dedicated parking space, which was wonderful as available street parking was limited over the holiday weekend."
United States
Steve K.
Downtown Boothbay Harbor Studio – Ocean Views, Dog-Friendly, Walk to Pier
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

Tugboat Inn

Tugboat Inn

10/10 Excellent
"We had a wonderful 2 night stay over Thanksgiving! Dinner in the Tugboat Restaurant was good. Convienient location to the shops and the Gardens aglow. "
Allison 2-night trip
Posted 1 day ago
Tugboat Inn

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 $200 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?

New 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 Boothbay Railway Village, or get out into nature at a spot like Cabbage Island. Burnt Island Living Lighthouse and Boothbay Harbor Marina 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.