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Search results; Over 1,000 homes in Portland

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Top guest favourite
Guest house in Portland
Guesthouse Farm Stay
1 bedroom, 2 beds, 1 private bathroom
31 Oct – 5 Nov
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4.98 out of 5 average rating, 348 reviews
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Flat in Portland
SUNNY PRIVATE 1 BEDROOM APARTMENT
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 575 reviews
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Guest house in Portland
Lakefront Living
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.82 out of 5 average rating, 17 reviews
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Farm stay in Portland
RV/Camper Farm Stay
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.91 out of 5 average rating, 97 reviews
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Home in East Hampton
CT River Retreat - Modern Home with CT River Views
3 bedrooms, 4 beds, 3 bathrooms
5–10 Sept
5.0 out of 5 average rating, 66 reviews
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Home in East Hampton
Historic Connecticut Country House Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.94 out of 5 average rating, 16 reviews
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Cottage in Portland
Lake Cottage Getaway
1 bedroom, 1 double bed, 1 bathroom
1–6 Sept
4.79 out of 5 average rating, 34 reviews
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Superhost
Guest house in Glastonbury
59 Old Maids Lane pool house
1 bedroom, 4 beds, WC
30 Sept – 5 Oct
4.75 out of 5 average rating, 126 reviews
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Home in New Britain
Bright & Private WHOLE HOUSE 4 YOU Near Everything
3 bedrooms, 6 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 118 reviews
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Houseboat in Glastonbury
Sunset River Boat
1 bedroom, 4 beds, 1 bathroom
6–11 Sept
New place to stay
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Home in East Hampton
Lovely, peaceful lakefront home.
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
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Home in Middletown
Cozy Family Home-Sleeps 6 Near Wesleyan & Weddings
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 8 reviews
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Home in Cromwell
Modern Ranch | 3 King Beds Near WesleyanUniversity
3 bedrooms, 3 king beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Cabin in East Hampton
Spacious family lakeside homestead
6 bedrooms, 9 beds, 2 bathrooms
7–12 Sept
4.88 out of 5 average rating, 24 reviews
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Superhost
Home in East Hampton
Grammy's Lake House on Lake Pocotopaug
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.7 out of 5 average rating, 70 reviews
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Home in East Hampton
Freshly Updated Home Sleeps 6, Steps from the Lake
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
4.88 out of 5 average rating, 8 reviews
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Home in East Hampton
East Hampton Lake Lodge
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 27 reviews
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Home in Manchester
Charming Cape Home, Close to All
4 bedrooms, 5 beds, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 114 reviews
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Home in East Hampton
Belltown House at Airline Trail
2 bedrooms, 5 beds, 1 bathroom
13–18 Sept
New place to stay