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Search results; Over 1,000 homes

Top guest favourite
Guest house in Cumberland
Cottage Under a Crabapple Tree
Studio, 1 bed, 1 private bathroom
10–15 Aug
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4.95 out of 5 average rating, 297 reviews
Guest favourite
Room in South Portland
HomeAwhile - Extended Stay Suites
4.93 out of 5 average rating, 137 reviews, 2 beds, 1 bathroom
9–14 Aug
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
12–17 Aug
Guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
Home in Westbrook
Cozy Cape in the Brook
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Top guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
4.99 out of 5 average rating, 294 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Oct
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 6 beds, 1.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Cabin in Freeport
Glamping cabin w/ kitchenette & full bath - 17
5.0 out of 5 average rating, 56 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Aug
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
4.99 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
Top guest favourite
Home in Windham
Maine Vacation Home on the Water
5.0 out of 5 average rating, 59 reviews, 4 bedrooms, 9 beds, 3 bathrooms
12–17 Sept
Cabin in Harrison
Nola’s Landing Getaway | Lakes & Mountains
New place to stay, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
Home in Raymond
Lakeside Cabin
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
Top guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
4.96 out of 5 average rating, 357 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
5.0 out of 5 average rating, 14 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Oct
Top guest favourite
Room in Freeport
Freeport, Maine
4.96 out of 5 average rating, 275 reviews, 1 queen bed, 1 bathroom
17–22 Oct
Top guest favourite
Yurt in Cumberland
Tree Yurt
4.93 out of 5 average rating, 205 reviews, 1 bedroom, 3 beds, WC
2–7 Aug
Top guest favourite
Home in Cumberland
Rustic charm close to Portland
4.96 out of 5 average rating, 334 reviews, 2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Casco
Waterview Lake House
4.96 out of 5 average rating, 23 reviews, 3 bedrooms, 11 beds, 1.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Tiny home in Windham
The Chickadee House on Pettingill Pond
4.97 out of 5 average rating, 234 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug