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Search results; Over 1,000 homes in Portland

Guest favourite
Cottage in Portland
Lake Cottage Getaway
1 bedroom, 1 bed, 1 private bathroom
9–14 Sept
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4.79 out of 5 average rating, 34 reviews
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, 352 reviews
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
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
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
Guest favourite
Home in East Hampton
Historic Connecticut Country House Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Sept
4.94 out of 5 average rating, 16 reviews
Home in Middletown
Historic Home 3 Mi to Middletown Main Street
6 bedrooms, 8 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in New Britain
Bright & Private WHOLE HOUSE 4 YOU Near Everything
3 bedrooms, 6 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 120 reviews
Top guest favourite
Guest house in Portland
CTriver water view in-law private apartment2bd/1ba
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 29 reviews
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, 52 reviews
Guest favourite
Cabin in East Hampton
Spacious family lakeside homestead
6 bedrooms, 9 beds, 2 bathrooms
14–19 Sept
4.88 out of 5 average rating, 24 reviews
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
Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
3 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
4.89 out of 5 average rating, 175 reviews
Superhost
Guest house in Glastonbury
59 Old Maids Lane pool house
1 bedroom, 4 beds, WC
30 Sept – 5 Oct
4.75 out of 5 average rating, 126 reviews
Top guest favourite
Home in Rocky Hill
Cozy Waterfront Home w/Hot Tub ~ Connecticut River
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
4.96 out of 5 average rating, 91 reviews
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
Home in Glastonbury
The Bee Hive
3 bedrooms, 3 queen beds, 2 bathrooms
13–18 Sept
4.64 out of 5 average rating, 56 reviews
Houseboat in Glastonbury
Sunset River Boat
1 bedroom, 4 beds, 1 bathroom
9–14 Sept
New place to stay
Guest favourite
Flat in Haddam
Welcome home! Cozy Apartment in Haddam
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 10 reviews