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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
19–24 Sept
,
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, 354 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
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
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
Superhost
Place to stay in Middletown
Rotterdam Room by Wesleyan
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
New place to stay
Guest favourite
Home in New Britain
Bright & Private WHOLE HOUSE 4 YOU Near Everything
3 bedrooms, 6 beds, 1 bathroom
9–14 Oct
4.95 out of 5 average rating, 121 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, 4 reviews
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
Guest favourite
Home in Manchester
Charming Cape Home, Close to All
4 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 119 reviews
Top guest favourite
Home in East Hampton
Fun on the Lake: Games, Dock, Slide, EV Charger
4 bedrooms, 7 beds, 3 bathrooms
19–24 Sept
4.99 out of 5 average rating, 85 reviews
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, 96 reviews
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, 177 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
Flat in Cromwell
Stylish Condo Retreat | Modern & Comfort
2 bedrooms, 1 bed, 1 bathroom
27 Sept – 2 Oct
New place to stay
Top guest favourite
Cottage in Rocky Hill
Connecticut Waterfront Cottage
3 bedrooms, 4 beds, 1 bathroom
26–31 Oct
4.99 out of 5 average rating, 87 reviews
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
Guest favourite
Home in Middletown
Cozy Family Home-Sleeps 6 Near Wesleyan & Weddings
2 bedrooms, 5 beds, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 10 reviews