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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 203 Cottages in Squirrel Island with updated reviews, rates, and availability.

Popham Beach Direct Oceanfront Cottage Steps to the sand
Interior

Popham Beach Direct Oceanfront Cottage Steps to the sand

9.8 out of 10, Exceptional, (58)
"Well taken care of and maintained. Comfortable."
Popham Beach Direct Oceanfront Cottage Steps to the sand
A Charming Waterfront Cottage with Touches of Elegance
Miscellaneous

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (104)
"I know the area very well but never would have known what this beautiful property had to offer from driving by all my life!David was a very welcoming host and easy to reach/helpul.House is immaculate and very well equipped with anything you could need. Beautiful mornings onthe sun porch with a bald eagle!will come back next year!"
A Charming Waterfront Cottage with Touches of Elegance
Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!
Interior

Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!

10.0 out of 10, Exceptional, (9)
"This is a charming log cabin in an historic log cabin development minutes from town, grocery shopping and within walking distance to a lovely park (Barrett). The "great room" has a wonderful fireplace, high ceilings, and comfortable couches and chairs. The large deck facing the water is beautiful, offering a spectacular view of Lewes Cove in Linekin Bay. You can hear loons, watch cormorants fishing and drying their wings on lobster trap platforms, and see bald eagles fly by and roost in nearby...
Waterfront Log Cabin Private Community Beach. CLOSEST TO TOWN less 10 min walk!
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
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
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)
"Sasanoa is a beautiful cabin in the woods. The vintage decor is lovely. The living area is very spacious, comfortable and perfect for two couples. Screened-in porch is great for reading and/or games. The location is extremely peaceful and quiet! "
Dreamy Wooded Cabin W/ Spacious Deck, Free WiFi, Secluded Location & More
Pets Stay Free! 3 Modern Cottages, 1st Floor King & Bunk Room + Loft w/Queen
Beach

Pets Stay Free! 3 Modern Cottages, 1st Floor King & Bunk Room + Loft w/Queen

10.0 out of 10, Exceptional, (39)
"This is a beautifully unique place to stay! This cozy cottage is charming and warm. The area is stunning with a gorgeous property, perfect for our pup! So many stunning places to see by the ocean… hikes, restaurants, botanical garden with the huge Trolls! Made memories with our family to hold dear. Thank you! Definitely would stay again! "
Pets Stay Free! 3 Modern Cottages, 1st Floor King & Bunk Room + Loft w/Queen
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
TV, books

Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown

9.8 out of 10, Exceptional, (32)
"Such a cute cottage perfect for two couples. Sunrise and sunset on the deck was awesome. Great location and easy walk into town. We loved it!"
Bayfront Cottage on Mill Cove w/ Private Dock & Furnished Deck - Walk Downtown
Boothbay Harbor Cottage Overlooking Mill Cove
TV

Boothbay Harbor Cottage Overlooking Mill Cove

10.0 out of 10, Exceptional, (18)
"We had a wonderful time at Mill Cove. Close to downtown and just the right size for a short getaway for my wife and I. "
Boothbay Harbor Cottage Overlooking Mill Cove
Sheepscot Overlook Cottage
Exterior

Sheepscot Overlook Cottage

10.0 out of 10, Exceptional, (4)
"Very convenient location for mid-Maine. Didn't know the unit was three levels from description. Kitchen fairly well stocked. TV in every room. Good internet. Checkout procedure was a little strict, stripping sheets, putting away all dishes, garbage delivered to dumpster."
Sheepscot Overlook Cottage
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Fridge, microwave, oven, stovetop

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

9.8 out of 10, Exceptional, (6)
"Overall this location is a great spot for those that dont need many amenities. There is no tv and no ac but the view and the breeze from the water make up for that! The space was clean and there was a grill plus Cooks Lobster house was a quick walk down the street! "
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage
Stunning Modern Maine Oceanfront Cottage - newly built in 2019
Outdoor dining

Stunning Modern Maine Oceanfront Cottage - newly built in 2019

10.0 out of 10, Exceptional, (21)
"Amazing, tranquility, absolutely worth planning a return visit."
Stunning Modern Maine Oceanfront Cottage - newly built in 2019
Snowball Hill Cottage - Near Pemaquid Beach & New Harbor Village.
Aerial view

Snowball Hill Cottage - Near Pemaquid Beach & New Harbor Village.

10.0 out of 10, Exceptional, (16)
"I stayed here while visiting family and friends in Nee Harbor. It is a cute little place, and the hosts were very helpful re: parking and checkout process. The property is accurately described on the website, and I would definitely stay again."
Snowball Hill Cottage - Near Pemaquid Beach & New Harbor Village.
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)
"I had an excellent visit. The kitchen was well stocked with utensils and small appliances. Everything was super clean; magazines and books were available (as well as good WiFi). I never turned the tv on as the view was spectacular. I wasn’t able to have an outdoor fire due to weather but everything was great. I hope to return. I look forward to doing more exploring as the area is beautiful. Also, very responsive with owners live next door. Thanks for offering up this quant little cabin for...
Cozy Cottage with spectacular salt water view / 3 Kayaks available/
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
TV, fireplace, books, stereo

Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

9.4 out of 10, Exceptional, (33)
"Very cozy house in an absolutely lovely spot. We really enjoyed the outdoor space and the peace and quiet. "
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
TV

Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

9.6 out of 10, Exceptional, (44)
"Absolutely beautiful views. Very well appointed and comfortable. "
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms
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
Spring Discount, Full Month 1,650-April through May, 1st Flr King/Loft
Interior

Spring Discount, Full Month 1,650-April through May, 1st Flr King/Loft

10.0 out of 10, Exceptional, (56)
"Just a classic maine cabin and great for our 3yr old lab. Will return!"
Spring Discount, Full Month 1,650-April through May, 1st Flr King/Loft
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)
"This is a small backyard apartment a block away from downtown Wiscasset. The house met our needs. The bed was comfortable. The kitchen was small but with enough equipment to prepare simple meals. The house was in walking distance of shops and restaurants in Wiscasset. There was a grill and patio for those who wanted to cook outside. The was a washer and dryer available. "
Dog-friendly historic cottage with deck, grill, kitchenette, & washer/dryer
Olde Post Office Cottage at Pemaquid Point
Fitness facility

Olde Post Office Cottage at Pemaquid Point

9.6 out of 10, Exceptional, (135)
"We stayed at the cottage for Christmas holiday. It was perfect. Beautifully decorated. Bed is super comfy. Kitchen had everything we needed. Special treat was the Maine maple syrupand a jar of blueberry jam we were given along with a beautiful Christmas card which I will be placing in a frame. We walked the Pemaquid loop every morning and enjoyed the beautiful ocean views. A total gem of a small cottage for two."
Olde Post Office Cottage at Pemaquid Point
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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Other property types in Squirrel Island

1 room luxury ocean front studio cottage
Miscellaneous

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (149)
"Very clean, amazinv views, perfect weekend!!!! "
1 room luxury ocean front studio cottage
Popham Beach Direct Oceanfront Cottage Steps to the sand
Interior

Popham Beach Direct Oceanfront Cottage Steps to the sand

9.8 out of 10, Exceptional, (58)
"Well taken care of and maintained. Comfortable."
Popham Beach Direct Oceanfront Cottage Steps to the sand
Beautiful House just a step from ocean
Interior

Beautiful House just a step from ocean

9.0 out of 10, Wonderful, (2)
"Lovely place for a couple and a child. Master bedroom was lovely. Water would not allow bathing but shower was ok in hall bath. The downstairs sleeping for two adults was a little difficult. Would have been nice to know upfront that the water was not potable. Nice touches with the set dining table and toiletries. View is amazing."
Beautiful House just a step from ocean
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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