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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
11–16 Sept
,
4.95 out of 5 average rating, 303 reviews
Superhost
Home in Raymond
Cozy Modern Lakefront — Foliage, Skiing, Skating
2 bedrooms, 2 beds, 1.5 bathrooms
21–28 Jun
New place to stay
Superhost
Treehouse in Casco
Nestled Treehouse | 65 Acres, Pond + Kayak
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
New place to stay
Guest favourite
Flat in New Gloucester
Cozy Winter Suite & Hot Tub
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.92 out of 5 average rating, 62 reviews
Top guest favourite
Home in Windham
The Quiet Perch - Modern Getaway with Water Views
2 bedrooms, 2 beds, 1.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.98 out of 5 average rating, 83 reviews
Top guest favourite
Cottage in Raymond
Lovely Lakefront Cottage - Book Your Fall GetAway!
3 bedrooms, 4 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Cabin in Oxford
Glamping Cabin with Hot Tub and Onsite Sauna
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Standish
Arthur's Place • Sebago Lakefront • Near Windham
2 bedrooms, 3 beds, 1.5 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Lisbon Falls
Charming Victorian farmhouse 1880's bedrooms-2
2 bedrooms, 2 queen beds, 1 bathroom
24–29 Oct
4.94 out of 5 average rating, 546 reviews
Superhost
Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 4 reviews
Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Cumberland
Rustic charm close to Portland
2 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
4.96 out of 5 average rating, 336 reviews
Top guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 387 reviews
Top guest favourite
Guest suite in Freeport
Studio Apartment in Freeport
3 beds, 1 bathroom
22–27 Sept
4.97 out of 5 average rating, 137 reviews
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 474 reviews
Flat in Cumberland
Brand new 1 Bedroom. Close to Portland
1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Guest house in Falmouth
Garden Guesthouse in Falmouth, 5 mins to Portland
1 bedroom, 2 king beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 7 reviews
Flat in Lisbon
Near Bates & Bowdoin Colleges + Local Nature Park!
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
New place to stay