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Cumberland County
Anytime
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Over 1,000 places
Guest favorite
Guest favorite
Cabin in Raymond
Rustic, cozy cabin on Sebago Lake. A hidden gem.
2 double beds
2 double beds
May 31 – Jun 5
May 31 – Jun 5
$160
night
$160 per night
4.93 out of 5 average rating, 144 reviews
4.93 (144)
Guest favorite
Guest favorite
Home in Gray
Little Sebago Lakefront Getaway
5 beds
5 beds
Apr 20 – 25
Apr 20 – 25
$300
night
$300 per night
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Guest favorite
Guest favorite
Guesthouse in Windham
Cottage on Black Brook Preserve
1 queen bed
1 queen bed
May 7 – 12
May 7 – 12
$125
night
$125 per night
5.0 out of 5 average rating, 218 reviews
5.0 (218)
Guest favorite
Guest favorite
Guest suite in New Gloucester
Many Moons Farm
3 beds
3 beds
Aug 17 – 22
Aug 17 – 22
$62
night
$62 per night
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Farm stay in Gray
The Retreat at Crystal Lake Farm
3 beds
3 beds
May 27 – Jun 1
May 27 – Jun 1
$155
night
$155 per night
4.88 out of 5 average rating, 241 reviews
4.88 (241)
Guest favorite
Guest favorite
Guest suite in Pownal
Maine Mystic Gardens, Family Friendly Suite
3 beds
3 beds
Apr 23 – 28
Apr 23 – 28
$89
night
$89 per night
4.97 out of 5 average rating, 73 reviews
4.97 (73)
Guest favorite
Guest favorite
Farm stay in Gray
Great Goat Get-away in Southern Maine!
4 beds
4 beds
Apr 29 – May 4
Apr 29 – May 4
$171
night
$171 per night
4.94 out of 5 average rating, 246 reviews
4.94 (246)
Guest favorite
Guest favorite
Guest suite in Gorham
Farmhouse stay, near lakes and St. Joe's College
Apr 22 – 27
Apr 22 – 27
$156
night
$156 per night
4.98 out of 5 average rating, 99 reviews
4.98 (99)
Guest favorite
Guest favorite
Apartment in Falmouth
Peaceful & Cozy Falmouth Getaway
5 beds
5 beds
Apr 24 – 29
Apr 24 – 29
$90
night
$90 per night
4.95 out of 5 average rating, 41 reviews
4.95 (41)
Guest favorite
Guest favorite
Cabin in Windham
Cozy Private Lake Getaway (Seasonal)
1 bed
1 bed
May 24 – 29
May 24 – 29
$158
night
$158 per night
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favorite
Guest favorite
Home in Windham
Private 3BR Ranch
4 beds
4 beds
May 9 – 14
May 9 – 14
$167
night
$167 per night
4.96 out of 5 average rating, 27 reviews
4.96 (27)
Guest favorite
Guest favorite
Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds
2 beds
Apr 30 – May 5
Apr 30 – May 5
$100
night
$100 per night
4.92 out of 5 average rating, 151 reviews
4.92 (151)
Guest favorite
Guest favorite
Home in Windham
Waterfront Gem walkable to Restaurants!
2 beds
2 beds
May 5 – 10
May 5 – 10
$149
night
$149 per night
4.95 out of 5 average rating, 64 reviews
4.95 (64)
Guest favorite
Guest favorite
Cottage in Falmouth
Cobb Cottage: Lake Beachfront Paradise!
4 beds
4 beds
May 4 – 9
May 4 – 9
$510
$350
night
$350 per night, originally $510
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Superhost
Superhost
Cottage in Windham
Relaxing 2 bed cottage on Little Sebago Lake
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
$220
night
$220 per night
4.9 out of 5 average rating, 10 reviews
4.9 (10)
Guest favorite
Guest favorite
Cottage in Pownal
Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
$279
$223
night
$223 per night, originally $279
4.99 out of 5 average rating, 322 reviews
4.99 (322)
Guest favorite
Guest favorite
Home in Gray
cozy 3 bedroom ranch with deck and screen porch
3 beds
3 beds
Apr 27 – May 2
Apr 27 – May 2
$200
night
$200 per night
4.95 out of 5 average rating, 43 reviews
4.95 (43)
Guest favorite
Guest favorite
Cabin in Freeport
Cozy Cottage-Near Harbor & Park
1 queen bed
1 queen bed
Apr 29 – May 4
Apr 29 – May 4
$134
night
$134 per night
4.98 out of 5 average rating, 469 reviews
4.98 (469)
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