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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
20–25 Sept
,
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
4.97 out of 5 average rating, 357 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
28 Sept – 3 Oct
5.0 out of 5 average rating, 70 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
Home in East Hampton
Historic Connecticut Country House Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
23–28 Sept
4.94 out of 5 average rating, 16 reviews
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Guest favourite
Flat in Portland
SUNNY PRIVATE 1 BEDROOM APARTMENT
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.88 out of 5 average rating, 579 reviews
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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
Home in New Britain
Bright & Private WHOLE HOUSE 4 YOU Near Everything
3 bedrooms, 6 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 122 reviews
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Superhost
Room in Middletown
Rotterdam Room by Wesleyan
1 queen bed, 1 bathroom
20–25 Sept
New place to stay
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Top guest favourite
Guest house in Portland
CTriver water view in-law private apartment2bd/1ba
2 bedrooms, 2 queen beds, 1 bathroom
30 Nov – 5 Dec
4.97 out of 5 average rating, 29 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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Houseboat in Glastonbury
Sunset River Boat
1 bedroom, 4 beds, 1 bathroom
26 Sept – 1 Oct
4.75 out of 5 average rating, 4 reviews
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Guest favourite
Home in East Hampton
Charming River Home
4 bedrooms, 7 beds, 2 bathrooms
2–7 Nov
4.82 out of 5 average rating, 50 reviews
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Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
3 bedrooms, 4 beds, 2 bathrooms
23–28 Nov
4.89 out of 5 average rating, 178 reviews
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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
28 Sept – 3 Oct
4.98 out of 5 average rating, 163 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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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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Top guest favourite
Home in Glastonbury
Walkable Glastonbury near Riverfront Park
3 bedrooms, 3 beds, 1.5 bathrooms
24–29 Sept
4.98 out of 5 average rating, 55 reviews
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Top guest favourite
Home in Newington
Urban Luxury in Central CT w/ free RV parking
4 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 97 reviews