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Search results; Over 1,000 homes in Portland

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Guest favourite
Cottage in Portland
Lake Cottage Getaway
1 bedroom, 1 bed, 1 private bathroom
1–6 Oct
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4.8 out of 5 average rating, 35 reviews
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Top guest favourite
Guest house in Portland
Guesthouse Farm Stay
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 358 reviews
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Top guest favourite
Home in East Hampton
CT River Retreat - Modern Home with CT River Views
3 bedrooms, 4 beds, 3 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 72 reviews
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Guest favourite
Farm stay in Portland
RV/Camper Farm Stay
1 bedroom, 2 beds, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 102 reviews
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Guest favourite
Flat in Portland
SUNNY PRIVATE 1 BEDROOM APARTMENT
1 bedroom, 1 queen bed, 1 bathroom
31 Oct – 5 Nov
4.88 out of 5 average rating, 579 reviews
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Guest favourite
Cabin in East Hampton
Spacious family lakeside homestead
6 bedrooms, 9 beds, 2 bathrooms
1–6 Oct
4.88 out of 5 average rating, 24 reviews
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Superhost
Room in Middletown
Rotterdam Room by Wesleyan
1 queen bed, 1 bathroom
1–6 Oct
New place to stay
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Guest favourite
Home in East Hampton
Historic Connecticut Country House Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
5–10 Oct
4.94 out of 5 average rating, 16 reviews
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Boat in Glastonbury
Trendy New England House Boat
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
4.57 out of 5 average rating, 7 reviews
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Top guest favourite
Cottage in East Hampton
Family Friendly Lake House Lake Pocotopaug Sunsets
3 bedrooms, 4 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 70 reviews
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Flat in Cromwell
Stylish Condo Retreat | Modern & Comfort
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
New place to stay
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Top guest favourite
Guest suite in Middletown
Guest Suite, 2nd floor, 3 bedrooms, near Downtown!
3 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 163 reviews
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Home in East Hampton
Belltown House at Airline Trail
2 bedrooms, 7 beds, 1 bathroom
4–9 Oct
New place to stay
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Guest favourite
Flat in Glastonbury
Quiet 2 bed room apt w/ private entrance.
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 463 reviews
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Superhost
Home in Portland
Brownstone Oasis
2 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.75 out of 5 average rating, 12 reviews
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Houseboat in Glastonbury
Sunset River Boat
1 bedroom, 4 beds, 1 bathroom
4–9 Oct
4.8 out of 5 average rating, 5 reviews
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Guest favourite
Home in East Hampton
Beautiful Lake House on Lake Pocotopaug
4 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.89 out of 5 average rating, 114 reviews
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Guest favourite
Home in East Hampton
Country getaway - pool, huge yard,
3 bedrooms, 8 beds, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 88 reviews
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Guest favourite
Guest house in East Hampton
Lakeview Carriage House
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.92 out of 5 average rating, 75 reviews