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Search results; Over 1,000 homes in Weston

Top guest favourite
Cottage in Weston
The River Loft
Studio, 2 beds, 1 private bathroom
1–6 Nov
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4.97 out of 5 average rating, 245 reviews
Top guest favourite
Home in Weston
River Cottage in Weston, CT
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 36 reviews
Home in Weston
Characterful iconic Weston lodge.
5 bedrooms, 5 beds, 4 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Home in Weston
3‑Acre Weston Retreat w/ Pool & Basketball Court
4 bedrooms, 4 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Weston
Modern Getaway in the Woods
5 bedrooms, 8 beds, 4 bathrooms
10–15 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Weston
Magical Weston Retreat
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
4.9 out of 5 average rating, 78 reviews
Top guest favourite
Flat in Weston
Tree Haven Loft, Grille, Firepit & Nature
1 bedroom, 2 queen beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Weston
Serenity in Weston - House, barn & pool
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Guest house in Weston
Nature Lovers Guesthouse
1 bedroom, 1 bed, 1 bathroom
8–13 Sept
4.98 out of 5 average rating, 56 reviews
Top guest favourite
Home in Weston
Staycation perfection
5 bedrooms, 6 beds, 3.5 bathrooms
1–6 Feb
5.0 out of 5 average rating, 13 reviews
Guest favourite
Room in Weston
Peace of Mind
1 bed, WC
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Wilton
Spectacular Renovated Barn
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Home in Weston
Still Stays - 3BR Ranch Near Westport & Fairfield
3 bedrooms, 4 beds, 3 bathrooms
27 Dec – 1 Jan
5.0 out of 5 average rating, 10 reviews
Villa in Weston
Great 4 bed 4.5 bath home w hot tub & heated pool
4 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
4.85 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Wilton
Designer Treehouse with Spa Bath
3 bedrooms, 3 beds, 1.5 bathrooms
17–22 Sept
4.98 out of 5 average rating, 47 reviews
Top guest favourite
Home in Fairfield
Cozy Cottage with Fire Pit, near Beach
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 229 reviews
Home in Westport
Classic New England Home for 8 | Leafy Westport
4 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
New place to stay
Top guest favourite
Guest suite in Weston
Garden Level 2 Bedroom Suite 5 Min to Westport
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Aug
5.0 out of 5 average rating, 51 reviews
Guest favourite
Home in Westport
Farmhouse 1899: Minutes to Downtown Westport, CT
3 bedrooms, 3 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 57 reviews