Search Cottages in Squirrel Island

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Compare 154 Cottages in Squirrel Island with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (65)
"Our stay was amazing and everything was just as we expected, and more! Highly recommend this log cabin in the woods in quiet Maine"
Amazing All-Season Sprucewold Cabin w/ Private Beach Club Access

Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

9.4 out of 10, Exceptional, (42)
"Beautiful location "
Gorgeous Waterfront Home on Westport Island with 2 Sunrooms

Olde post office

9.6 out of 10, Exceptional, (133)
"It looks straight out of a storybook with great amenities and lovely grounds. We were able to have a fire in the fire pit which was so much fun and being close to the lighthouse was a huge perk. The host was kind and accessible. I would definitely composer staying at this property again. "
Olde post office

Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

10.0 out of 10, Exceptional, (51)
"Perfect cottage for visiting Maine's small coastal towns. Comfortable and convenient. Great bird watching. Wonderful host. All around perfect stay."
Maine Waterfront Cottage: Nestled on an acre of land, with 500ft of shore front

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

A Charming Waterfront Cottage with Touches of Elegance

10.0 out of 10, Exceptional, (96)
"Beautiful cottage with an amazing view of the bay. Great porch where we spent most of our time. Very convenient to Damariscotta. Great setting for two couples. "
A Charming Waterfront Cottage with Touches of Elegance

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

9.4 out of 10, Exceptional, (30)
"This house was amazing. It was way better than we expected after looking through the pictures online. The outdoor space and the house itself are beautiful and the pictures do it zero justice. We were worried at first about the lack of AC, but the house cooled right down once we opened the windows let the air in. I highly recommend this place if you’re looking to visit Boothbay. It was so close to the main area, but you couldn’t even tell- it felt like you were immersed in nature."
Appalachee Pond Waterfront Cottage | Decks, Sunroom, Dock with Kayaks & Canoe

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

8.8 out of 10, Excellent, (13)
"Nice views of tidal river "
Newly renovated waterfront dog-friendly cottage with dock, patio, & washer/dryer

Two separate dog-friendly homes with water views & Linekin Bay Resort access

8.0 out of 10, Very Good, (5)
"This was a beautiful place to stay and had more parking than we expected. The only hiccups we had was that the check in code we were given was one digit off from what it actually was so we had a little trouble getting into the house. Also there is an outlet that was uncovered in the bedroom and we had a child touch it. Luckily the child wasn’t harmed but this should definitely be addressed if there’s any little ones staying on the property. The houses were very clean and the only reason I gave...
Two separate dog-friendly homes with water views & Linekin Bay Resort access

Steps to Your Private 100 Feet of Lake Front -

8.4 out of 10, Very Good, (16)
"Bill was so very nice and 100% accommodating. His place was very neat and clean. The property is very well maintained, private and peaceful. His cousin , Darcy, lives 2 doors down and is readily available should there be any questions or concerns.We enjoyed the lions at night and the stars were mesmerizing along with the fireflies. Thank you for a lovely stay and we look forward to returning next year."
Steps to Your Private 100 Feet of Lake Front -

Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME

10.0 out of 10, Exceptional, (27)
"My sisters and I enjoyed our stay at this home, which is very comfortable, clean, and well stocked. Loved the rocking chairs looking out onto the water. Would definitely love to return some day."
Oceanfront home with private deep water dock on Harmon Harbor, Georgetown, ME

As much "an experience" as shelter, Kinsale delights everyone of all ages.

9.2 out of 10, Wonderful, (13)
"Fantastic !!!"
As much "an experience" as shelter, Kinsale delights everyone of all ages.

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

Cheerful Cottage Close to Everything 13

9.6 out of 10, Exceptional, (9)
"Cozy, clean, and conveniently located for accessing many peninsulas. Just off Rt 1- noise not a problem."
Cheerful Cottage Close to Everything 13

Your Windows To The Ocean, Lobstering Village, And Private Floating Dock!

10.0 out of 10, Exceptional, (48)
"We enjoyed watching the sunrise while having a cup of coffee. The views are fantastic and it is in a very quiet area. It was the perfect spot for our time in the area. "
Your Windows To The Ocean, Lobstering Village, And Private Floating Dock!

A Cozy Retreat on Southport Island

9.8 out of 10, Exceptional, (25)
"Adorable spot. Classic and cozy seaside cottage with the amazing boat house as an extra bonus. We walked to Robinson’s Wharf every night. Delish! We wanted to stay longer, oh well, next time! "
A Cozy Retreat on Southport Island

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

Spacious 1 Bedroom Cottage Close to Everything 5

10.0 out of 10, Exceptional, (6)
"Everything was great. We had a minor ‘blip’ when the morning of our arrival, the hot water went out in our cabin. Our host reached out and offered an alternative. No biggie and everything went well. We appreciated Jeff's willingness to find a solution. "
Spacious 1 Bedroom Cottage Close to Everything 5

Lakefront Home w/ Beautiful Water Views Dock and Canoes Available - Dogs OK

8.0 out of 10, Very Good, (10)
"I wish I could give 5 stars, but I can’t. We arrived on a Tuesday afternoon, at 4:30. We unlocked the door and entered into a powerful smell. Campfire. Black soot up the front of the fireplace and the smell was awful. And of coarse, we are super sensitive to the smell. Looking around, I found the couch to be filthy, every screen had nasty cobwebs, dirt on the floor, bedding filthy, mold on the shower floor, Bathroom faucet was disgusting and obviously not cleaned . I was profoundly disappointed,...
Lakefront Home w/ Beautiful Water Views Dock and Canoes Available - Dogs OK

Redbird Cottage. Charming respite w/ large wrap-around porch and ocean views

10.0 out of 10, Exceptional, (22)
"We loved our stay at beautiful Redbird Cottage! This was our first time visiting Maine and Cherie made us feel welcome right from the start! Thank you, Cherie, for the gift bag with local goodies and recommendations for places and food, and checking in with us to ensure we had everything we needed. We did! You provided everything and more! I took full advantage of the breathtaking views from the front porch every morning with coffee and the incredible sunsets every evening. And a bit of rain on...
Redbird Cottage. Charming respite w/ large wrap-around porch and ocean views
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

East Boothbay Waterfront One room Condo.Waterview from in side this room

9.8 out of 10, Exceptional, (127)
"perfect love to be back next year"
East Boothbay Waterfront One room Condo.Waterview from in side this room

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

8.2 out of 10, Very Good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach

1 room luxury ocean front studio cottage

9.6 out of 10, Exceptional, (148)
"What a perfect place to unwind and watch the sunrise. "
1 room luxury ocean front studio 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.

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