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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
10–15 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
27 Sept – 2 Oct
4.98 out of 5 average rating, 353 reviews
Guest favourite
Farm stay in Portland
RV/Camper Farm Stay
1 bedroom, 2 beds
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
20–25 Sept
4.88 out of 5 average rating, 578 reviews
Superhost
Rooms in Middletown
Ventures 2
2 bedrooms, 2 beds
11–16 Sept
4.83 out of 5 average rating, 36 reviews
Guest favourite
Home in East Hampton
Historic Connecticut Country House Retreat
4 bedrooms, 4 beds
13–18 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Middletown
Beautiful Sunny Apartment in Historic Village
3 bedrooms, 4 beds
4–9 Oct
4.83 out of 5 average rating, 266 reviews
Top guest favourite
Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds
25–30 Oct
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Haddam
The Doll House
1 bedroom, 3 beds
11–16 Oct
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Farm stay in Glastonbury
Rustic Farmhouse by the River (Duplex)
1 bedroom, 1 king bed
4–9 Oct
4.98 out of 5 average rating, 189 reviews
Guest favourite
Home in East Hampton
Waterfront Lake House
4 bedrooms, 5 beds
10–15 Sept
4.83 out of 5 average rating, 77 reviews
Top guest favourite
Guest house in East Hampton
Your Own Barn Loft Suite Among the Treetops
1 bedroom, 1 queen bed
14–19 Sept
4.88 out of 5 average rating, 75 reviews
Guest favourite
Home in East Hampton
Freshly Updated Home Sleeps 6, Steps from the Lake
3 bedrooms, 3 beds
20–25 Oct
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Haddam
Cozy Comforts!
1 bedroom, 1 bed
27 Sept – 2 Oct
4.99 out of 5 average rating, 163 reviews
Guest favourite
Home in Middletown
Cozy Family Home-Sleeps 6 Near Wesleyan & Weddings
2 bedrooms, 5 beds
9–14 Nov
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in East Haddam
Romantic Getaway at The Lake!
1 bedroom, 1 bed
1–6 Nov
4.93 out of 5 average rating, 357 reviews
Top guest favourite
Farm stay in Glastonbury
John Hollister home on the farm
3 bedrooms, 5 beds
10–15 Sept
5.0 out of 5 average rating, 34 reviews
Guest favourite
Room in Middletown
Hl. Ventures
1 bed
25–30 Sept
4.75 out of 5 average rating, 65 reviews
Superhost
Flat in Middletown
Stylish Stay Near Wesleyan - 2BR
2 bedrooms, 2 beds
26 Sept – 1 Oct
4.7 out of 5 average rating, 20 reviews