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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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4.97 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
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
21–26 Sept
4.94 out of 5 average rating, 16 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
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
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
Beautiful Lake House on Lake Pocotopaug
4 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.89 out of 5 average rating, 114 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
Place to stay in Middletown
A Luxury Estate Spacious Historic~White Lion Manor
9 bedrooms, 10 beds, 8.5 bathrooms
9–14 Nov
4.96 out of 5 average rating, 105 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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Guest suite in Glastonbury
Acorn Retreat in the Woods
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Oct
4.67 out of 5 average rating, 6 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
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
Cottage in East Hampton
Charming 3 bedroom cottage on Lake Pocotopaug
3 bedrooms, 6 beds, 2 bathrooms
25–30 May
4.91 out of 5 average rating, 56 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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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
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