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Top guest favourite
Guest house in Cumberland
Cottage Under a Crabapple Tree
Studio, 1 bed, 1 private bathroom
28 Oct – 2 Nov
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4.95 out of 5 average rating, 313 reviews
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Guest favourite
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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Top guest favourite
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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Top guest favourite
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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Top guest favourite
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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Guest favourite
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 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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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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Top guest favourite
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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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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Top guest favourite
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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Top guest favourite
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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Guest favourite
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
Photo 1 of 24
Top guest favourite
Home in Windham
Peaceful River House - 20 minutes from Portland!
3 bedrooms, 4 beds, 3 bathrooms
15–20 Oct
4.89 out of 5 average rating, 46 reviews
Photo 1 of 29
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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Top guest favourite
Home in Casco
Family Camp at Coffee Pond, private home for 8
3 bedrooms, 6 beds, 2 bathrooms
13–18 Oct
4.97 out of 5 average rating, 70 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
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Top guest favourite
Home in Portland
Wall St. Retreat: Family-Ready Portland Home
3 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 33 reviews