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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
27 Sept – 2 Oct
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4.98 out of 5 average rating, 355 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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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
Cottage in Portland
Lake Cottage Getaway
1 bedroom, 1 double bed, 1 bathroom
19–24 Sept
4.79 out of 5 average rating, 34 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, 579 reviews
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Superhost
Home in Cromwell
Willowbrook Retreat
3 bedrooms, 3 beds, 4.5 bathrooms
31 Oct – 5 Nov
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Guest favourite
Guest house in Cromwell
The New England Tiny Home Experience—Coffee & More
1 bedroom, 2 beds, 1 bathroom
1–6 Jul
4.98 out of 5 average rating, 55 reviews
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Guest favourite
Home in East Hampton
Country getaway - pool, huge yard,
3 bedrooms, 8 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 87 reviews
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Superhost
Home in Portland
Brownstone Oasis
2 bedrooms, 4 beds, 1 bathroom
18–23 Oct
4.75 out of 5 average rating, 12 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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Top guest favourite
Flat in Middletown
Quaint 2br apt- 1 block walk to Wesleyan & Main St
2 bedrooms, 3 beds, 1 bathroom
12–17 Nov
4.94 out of 5 average rating, 922 reviews
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Top guest favourite
Home in East Hampton
East Hampton Lake Lodge
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 30 reviews
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Top guest favourite
Home in Middletown
Renovated Single Family Home in Central CT
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 17 reviews
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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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Top guest favourite
Farm stay in Glastonbury
Woolly Acres Farm
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.99 out of 5 average rating, 299 reviews
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Guest favourite
Guest house in East Hampton
Lakeview Carriage House
2 bedrooms, 3 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.92 out of 5 average rating, 75 reviews
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Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
3 bedrooms, 4 beds, 2 bathrooms
17–22 Nov
4.89 out of 5 average rating, 178 reviews
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Guest favourite
Room in Middletown
Bedroom in Georgian mansion
1 queen bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 15 reviews