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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, 347 reviews
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Farm stay in Portland
RV/Camper Farm Stay
1 bedroom, 2 beds
6–11 Sept
4.91 out of 5 average rating, 97 reviews
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Flat in Portland
SUNNY PRIVATE 1 BEDROOM APARTMENT
1 bedroom, 1 queen bed
20–25 Sept
4.89 out of 5 average rating, 575 reviews
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Cottage in Portland
Lake Cottage Getaway
1 bedroom, 1 double bed
1–6 Sept
4.79 out of 5 average rating, 34 reviews
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Room in Middletown
Hl. Ventures
1 bed
1–6 Sept
4.74 out of 5 average rating, 62 reviews
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Flat in Middletown
Beautiful Sunny Apartment in Historic Village
3 bedrooms, 4 beds
6–11 Sept
4.83 out of 5 average rating, 265 reviews
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Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds
25–30 Oct
5.0 out of 5 average rating, 19 reviews
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Home in Middletown
Cozy Family Home-Sleeps 6 Near Wesleyan & Weddings
2 bedrooms, 5 beds
9–14 Nov
5.0 out of 5 average rating, 8 reviews
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Home in East Haddam
Romantic Getaway at The Lake!
1 bedroom, 1 bed
25–30 Oct
4.93 out of 5 average rating, 352 reviews
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Farm stay in Glastonbury
John Hollister home on the farm
3 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 33 reviews
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Guest house in Cromwell
The New England Tiny Home Experience—Coffee & More
1 bedroom, 2 beds
13–18 Sept
4.98 out of 5 average rating, 49 reviews
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Superhost
Guest house in Portland
Lakefront Living
1 bedroom, 2 beds
7–12 Sept
4.82 out of 5 average rating, 17 reviews
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Flat in Middletown
Cozy Apartment Near Wesleyan and Town Center
1 bedroom, 2 beds
20–25 Sept
4.86 out of 5 average rating, 76 reviews
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Top guest favourite
Place to stay in Middletown
A Luxury Estate Spacious Historic~White Lion Manor
9 bedrooms, 10 beds
25–30 Oct
4.96 out of 5 average rating, 101 reviews
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Home in Haddam
The Doll House
1 bedroom, 3 beds
21–26 Oct
5.0 out of 5 average rating, 64 reviews
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Superhost
Rooms in Middletown
Ventures 2
2 bedrooms, 2 beds
1–6 Sept
4.82 out of 5 average rating, 34 reviews
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Superhost
Flat in Middletown
Stylish Stay Near Wesleyan - 2BR
2 bedrooms, 2 beds
21–26 Sept
4.7 out of 5 average rating, 20 reviews
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Home in Middletown
Historic Home 3 Mi to Middletown Main Street
6 bedrooms, 8 beds
14–19 Sept
5.0 out of 5 average rating, 3 reviews
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Farm stay in Glastonbury
Historic Farmhouse by the River (Duplex)
1 bedroom, 1 king bed
21–26 Oct
5.0 out of 5 average rating, 212 reviews