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Top guest favourite
Yurt in Cumberland
Tree Yurt
1 bedroom, 3 beds, 0.5 private bathroom
4–9 Oct
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4.93 out of 5 average rating, 212 reviews
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Chalet in Standish
Blueberry Hill
5 bedrooms, 10 beds, 2.5 bathrooms
15–20 Oct
4.96 out of 5 average rating, 263 reviews
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Cottage in Harpswell
Updated Historic Cottage, Private Waterfront, 5BR
5 bedrooms, 7 beds, 2 bathrooms
16–21 Oct
5.0 out of 5 average rating, 19 reviews
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Home in Windham
Highland Lake Cottage/Waterfront/Dock/Kayaks
3 bedrooms, 6 beds, 1.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Portland
Top Deck - Portland Property with Views!
3 bedrooms, 10 beds, 2.5 bathrooms
25–30 Oct
4.92 out of 5 average rating, 305 reviews
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Top guest favourite
Home in Old Orchard Beach
Luxury Home w/HOT TUB & Fire Pit
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 237 reviews
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Home in Windham
Stunning, pets ok, private lake-house with dock.
3 bedrooms, 5 beds, 1 bathroom
24–31 Oct
5.0 out of 5 average rating, 27 reviews
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Cottage in Raymond
Lovely Lakefront Cottage - Book Your Fall GetAway!
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 98 reviews
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Home in Raymond
37(A) Shore Rd, Raymond ME
4 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 30 reviews
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Home in Windham
Serene Modern Lakefront Escape l 20 min Portland
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 25 reviews
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Cottage in Windham
*NEW* Peaceful Waterfront Retreat
2 bedrooms, 4 beds, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Cumberland
Brand new 1 Bedroom. Close to Portland
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
2–7 Oct
4.96 out of 5 average rating, 179 reviews
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Home in Raymond
Lakeside Cabin
2 bedrooms, 3 beds, 1 bathroom
1–6 May
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Cumberland
Forest Lake Cottage
2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
4.96 out of 5 average rating, 76 reviews
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Home in Old Orchard Beach
Unique and Stunning Beachfront property Greygoose
4 bedrooms, 9 beds, 3 bathrooms
8–13 Nov
4.92 out of 5 average rating, 189 reviews
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Guest suite in Windham
Millers Private Studio on Highland Lake
2 beds, 1 bathroom
13–18 Oct
4.93 out of 5 average rating, 224 reviews
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Home in Windham
Beautiful Sebago Lake Getaway!
2 bedrooms, 5 beds, 1.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest suite in Freeport
Waterfront Coastal Apartment | 5 Min to LLBean
1 bedroom, 2 beds, 1 bathroom
17–22 Oct
4.97 out of 5 average rating, 287 reviews