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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
15–20 Nov
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4.97 out of 5 average rating, 245 reviews
Home in Weston
Characterful iconic Weston lodge.
5 bedrooms, 5 beds, 4 bathrooms
15–20 Sept
New place to stay
Top guest favourite
Home in Weston
Staycation perfection
5 bedrooms, 6 beds, 3.5 bathrooms
27 Dec – 1 Jan
5.0 out of 5 average rating, 13 reviews
Guest favourite
Room in Weston
Peace of Mind
1 bed, WC
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Weston
Tree Haven Loft, Grille, Firepit & Nature
1 bedroom, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Weston
River Cottage in Weston, CT
2 bedrooms, 2 beds, 1 bathroom
17–22 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Weston
3‑Acre Weston Retreat w/ Pool & Basketball Court
4 bedrooms, 4 beds, 3.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 30 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, 79 reviews
Top guest favourite
Guest house in Weston
Nature Lovers Guesthouse
1 bedroom, 1 bed, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 57 reviews
Guest favourite
Guest suite in Westport
The Tavern Room
1 bedroom, 1 bed, 1 bathroom
7–12 Oct
4.87 out of 5 average rating, 157 reviews
Guest favourite
Guest house in Wilton
The Ciderhouse Cottage - private escape in Wilton
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.93 out of 5 average rating, 54 reviews
Guest favourite
Home in Weston
Serenity in Weston - House, barn & pool
2 bedrooms, 3 beds, 1 bathroom
16–21 Sept
4.93 out of 5 average rating, 14 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
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
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
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
Room in Weston
Private Bedroom & Bath in Beautiful Weston
1 queen bed, 1 bathroom
18–23 Oct
New place to stay
Top guest favourite
Flat in Wilton
Designer Treehouse with Spa Bath
3 bedrooms, 3 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.98 out of 5 average rating, 47 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