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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
1–6 Nov
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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
31 Oct – 5 Nov
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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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
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
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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Guest favourite
Cottage in Portland
Lake Cottage Getaway
1 bedroom, 1 double bed, 1 bathroom
1–6 Oct
4.8 out of 5 average rating, 35 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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Rooms in Middletown
Spacious Apartment Near Wesleyan Fenced-in Yard
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.76 out of 5 average rating, 25 reviews
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Guest favourite
Room in Middletown
Hl. Ventures
1 bed, 1 bathroom
1–6 Oct
4.75 out of 5 average rating, 65 reviews
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Room in Cromwell
Comfy Colonial loft room
2 beds, 1 bathroom
1–6 Oct
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
3–8 Oct
New place to stay
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Home in Glastonbury
The Bee Hive
3 bedrooms, 3 queen beds, 2 bathrooms
4–9 Oct
4.64 out of 5 average rating, 56 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
1–6 Oct
4.98 out of 5 average rating, 163 reviews
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Guest favourite
Flat in Middletown
Updated 2-bedroom Near Wesleyan-Middletown
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 108 reviews
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Guest favourite
Home in East Hampton
Beautiful lakefront home, 4bed 2.5ba
4 bedrooms, 4 beds, 2.5 bathrooms
26–31 Oct
4.86 out of 5 average rating, 149 reviews
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Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
3 bedrooms, 4 beds, 2 bathrooms
1–6 Dec
4.89 out of 5 average rating, 178 reviews
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Superhost
Home in Middletown
Cozy Colonial House | Centrally Located
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.77 out of 5 average rating, 92 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