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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, 356 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
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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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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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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Home in Middletown
Historic Home 3 Mi to Middletown Main Street
6 bedrooms, 8 beds, 2.5 bathrooms
18–23 Oct
5.0 out of 5 average rating, 4 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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Guest favourite
Home in New Britain
Bright & Private WHOLE HOUSE 4 YOU Near Everything
3 bedrooms, 6 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 121 reviews
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Superhost
Room in Middletown
Amsterdam Room by Wesleyan
1 queen bed, 1 bathroom
19–24 Oct
New place to stay
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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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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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Top guest favourite
Home in Rocky Hill
Cozy Waterfront Home w/Hot Tub ~ Connecticut River
3 bedrooms, 4 beds, 3 bathrooms
25–30 Oct
4.96 out of 5 average rating, 92 reviews
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Guest favourite
Flat in Glastonbury
Quiet 2 bed room apt w/ private entrance.
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
4.89 out of 5 average rating, 463 reviews
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Top guest favourite
Home in Manchester
Hike & Stay | 3 BR w/ Fenced Yard
3 bedrooms, 3 beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 21 reviews
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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
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Top guest favourite
Home in Glastonbury
Walkable Glastonbury near Riverfront Park
3 bedrooms, 3 beds, 1.5 bathrooms
24–29 Sept
4.98 out of 5 average rating, 54 reviews
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Home in Glastonbury
The Bee Hive
3 bedrooms, 3 queen beds, 2 bathrooms
20–25 Sept
4.64 out of 5 average rating, 56 reviews
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Guest favourite
Home in East Hampton
Clean private home near Lake Pocotopaug!
3 bedrooms, 5 beds, 1 bathroom
29 Sept – 4 Oct
4.94 out of 5 average rating, 109 reviews