Search Cottages in Squirrel Island

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 205 Cottages in Squirrel Island with updated reviews, rates, and availability.

Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer
Outdoor dining

Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer

9.8 out of 10, Exceptional, (17)
"Very convinience close to main restaurant and the place was very clean"
Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer
Outdoor dining

Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer

8.8 out of 10, Excellent, (14)
"Our family had a great stay here. Lovely location."
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer
Salty Breeze Cottage
Fridge, microwave, oven, stovetop

Salty Breeze Cottage

10.0 out of 10, Exceptional, (6)
"We absolutely loved this peaceful spot by the water! It’s a quiet location with great water access, and the property is very well managed and maintained. We’d love to return!"
Salty Breeze Cottage
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Interior

Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town

9.6 out of 10, Exceptional, (25)
"Convenient and cozy. Lovely wooded lot with views. "
Waterfront Paradise with Dock, Big Yard, Sundeck & Epic Bay Views | Near Town
Enjoyable 1-bedroom rustic cottage in Southport.
Terrace/patio

Enjoyable 1-bedroom rustic cottage in Southport.

Enjoyable 1-bedroom rustic cottage in Southport.
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Terrace/patio

Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

9.6 out of 10, Exceptional, (66)
"Great spot"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Exterior

Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace

9.0 out of 10, Wonderful, (64)
"Wonderful views."
Dog-friendly, bayfront home - gorgeous ocean views, private balcony & fireplace
Olde Post Office Cottage at Pemaquid Point
Fitness facility

Olde Post Office Cottage at Pemaquid Point

9.6 out of 10, Exceptional, (136)
"This is our second time staying here, and as before, it was delightful. Obvious that the owner puts a lot of care and thought into the place."
Olde Post Office Cottage at Pemaquid Point
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Beach

Cozy Cottage with spectacular salt water view / 3 Kayaks available/

9.8 out of 10, Exceptional, (38)
"The property is exactly like the pictures but better. The view is amazing, location is quite and comfortable. Easy access the many towns & hiking locations. Would stay again."
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
Fridge, microwave, oven, stovetop

Thorburn - Experience a classic ME vacation at this beautiful summer cottage

9.8 out of 10, Exceptional, (13)
"Absolutely loved our late summer stay at this dreamy cottage in Harpswell. The cottage reminded us of childhood summer stays in coastal New England and the nostalgia was real and definitely welcome."
Thorburn - Experience a classic ME vacation at this beautiful summer cottage
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
TV, DVD player, books, video library

Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor

9.8 out of 10, Exceptional, (43)
"Great spot in Southport Island. Highly recommend."
Romley House | Deck & New Luxe Kitchen | Near Boothbay Harbor
Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Terrace/patio

Charming Cottage on the Great Pond in Boothbay Harbor, Maine

Charming Cottage on the Great Pond in Boothbay Harbor, Maine
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Property grounds

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

9.4 out of 10, Exceptional, (16)
"Loved the location."
Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage
Updated Tiny House: Walk to Wiscasset Village
Exterior

Updated Tiny House: Walk to Wiscasset Village

8.0 out of 10, Very Good, (5)
"Great location, easy to get to lots of coastal regions. Property is clean and cozy."
Updated Tiny House: Walk to Wiscasset Village
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities
Interior

Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great property, great host, just as described."
Marsh View Cottage in Arrowsic is a perfect nature getaway w/ nearby amenities
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Interior

Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room

10.0 out of 10, Exceptional, (50)
"Cozy spot on a beautiful beach - hard to beat!"
Driftwood Oceanfront Cottage at Popham Beach Spectacular views from every room
Unique oceanfront home with a deck, tons of natural light, & amazing views
Interior

Unique oceanfront home with a deck, tons of natural light, & amazing views

8.6 out of 10, Excellent, (53)
"Beautiful lcation, private & quiet"
Unique oceanfront home with a deck, tons of natural light, & amazing views
Popham Beach Direct Oceanfront Cottage Steps to the sand
Interior

Popham Beach Direct Oceanfront Cottage Steps to the sand

10.0 out of 10, Exceptional, (62)
"Great location and very clean Camp with great views. "
Popham Beach Direct Oceanfront Cottage Steps to the sand
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Terrace/patio

Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More

9.8 out of 10, Exceptional, (18)
"Loved the authenticity of the cabin. One gets a true feel for what it must have been like to stay here 50 to 100 years ago, but with today’s modern conveniences. Cabin was very clean and Vacasa was fabulous to deal with. We had a wonderful two days here!"
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Waterfront Cottage
Fridge, microwave, oven, stovetop

Waterfront Cottage

9.2 out of 10, Wonderful, (24)
"Perfect for us close location wise for visiting my so at college, close to freeport for shopping, house was so comfortable and had amazing views. Everything you needed was supplied, cant wait to visot again"
Waterfront Cottage
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Squirrel Island with Expedia?
Booking a cottage in Squirrel Island is as simple as clicking on your travel dates and picking your ideal place for outdoor relaxation and recreation. From upmarket retreats to affordable properties and cottages that come with amenities like laundry facilities, Expedia has something for all tastes. As for unbeatable deals? We’ve got them as well!
How can I find cheap cottages in Squirrel Island?
The easiest way to uncover cheap cottages in Squirrel Island is with Expedia’s convenient filter tool. Narrow down your search by star rating, budget and amenities to grab unbeatable deals in just a few keystrokes.