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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
19–24 Sept
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4.79 out of 5 average rating, 34 reviews
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Top guest favourite
Guest house in Portland
Guesthouse Farm Stay
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 354 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
21–26 Sept
5.0 out of 5 average rating, 69 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, 101 reviews
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Guest favourite
Home in East Hampton
Historic Connecticut Country House Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Flat in Portland
SUNNY PRIVATE 1 BEDROOM APARTMENT
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 578 reviews
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Superhost
Place to stay in Middletown
Rotterdam Room by Wesleyan
1 bedroom, 1 queen bed, 1 bathroom
28 Sept – 3 Oct
New place to stay
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Home in Middletown
Historic Home 3 Mi to Middletown Main Street
6 bedrooms, 8 beds, 2.5 bathrooms
18–23 Oct
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
21–26 Sept
4.88 out of 5 average rating, 24 reviews
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Guest favourite
Home in Manchester
Charming Cape Home, Close to All
4 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 119 reviews
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Top guest favourite
Home in Rocky Hill
Cozy Waterfront Home w/Hot Tub ~ Connecticut River
3 bedrooms, 4 beds, 3 bathrooms
25–30 Oct
4.96 out of 5 average rating, 91 reviews
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Home in Glastonbury
The Bee Hive
3 bedrooms, 3 queen beds, 2 bathrooms
20–25 Sept
4.64 out of 5 average rating, 56 reviews
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Room in Cromwell
Comfy Colonial loft room
2 beds, 1 bathroom
16–21 Sept
4.87 out of 5 average rating, 23 reviews
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Rooms in Newington
Cozy 2 bedroom and 1 bath room, private entrance
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
New place to stay
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Guest favourite
Flat in Haddam
Welcome home! Cozy Apartment in Haddam
2 bedrooms, 2 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Home in East Hampton
Lake Me Home
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.77 out of 5 average rating, 31 reviews
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Flat in Berlin
New England Getaway
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.81 out of 5 average rating, 47 reviews
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Top guest favourite
Home in Manchester
Hike & Stay | 3 BR w/ Fenced Yard
3 bedrooms, 3 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Flat in Middletown
Lakeside apartment 2.5 miles from Wesleyan campus!
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.84 out of 5 average rating, 205 reviews