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Search results; Over 1,000 homes in Weston

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Top guest favourite
Home in Weston
River Cottage in Weston, CT
2 bedrooms, 2 beds, 1 private bathroom
8–13 Sept
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5.0 out of 5 average rating, 36 reviews
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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, 29 reviews
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Home in Weston
Modern Getaway in the Woods
5 bedrooms, 8 beds, 4 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
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Home in Weston
Magical Weston Retreat
3 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.9 out of 5 average rating, 78 reviews
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Cottage in Weston
The River Loft
2 beds, 1 bathroom
1–6 Nov
4.97 out of 5 average rating, 242 reviews
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Flat in Weston
Tree Haven Loft, Grille, Firepit & Nature
1 bedroom, 2 queen beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 15 reviews
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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
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Room in Weston
Peace of Mind
1 bed, WC
1–6 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Weston
Staycation perfection
5 bedrooms, 6 beds, 3.5 bathrooms
1–6 Feb
5.0 out of 5 average rating, 13 reviews
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Home in Weston
Characterful iconic Weston lodge.
4 bedrooms, 4 king beds, 4 bathrooms
7–12 Sept
New place to stay
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Guest house in Weston
Nature Lovers Guesthouse
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.98 out of 5 average rating, 56 reviews
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Home in Weston
Still Stays - 3BR Ranch Near Westport & Fairfield
3 bedrooms, 4 beds, 3 bathrooms
19–24 Feb
5.0 out of 5 average rating, 10 reviews
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Superhost
Home in Wilton
Spectacular Renovated Barn
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
4.94 out of 5 average rating, 17 reviews
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Home in Redding
Retreat with Heated Pool, 1 Mile to NYC Train
4 bedrooms, 5 beds, 2.5 bathrooms
14–19 Sept
4.99 out of 5 average rating, 104 reviews
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Home in Norwalk
Spacious Home Near Beach + Train Sleeps 10+ | Yard
4 bedrooms, 6 beds, 2 bathrooms
24–29 Oct
4.96 out of 5 average rating, 45 reviews
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Villa in Weston
Great 4 bed 4.5 bath home w hot tub & heated pool
4 bedrooms, 5 beds, 3 bathrooms
3–8 Sept
4.85 out of 5 average rating, 26 reviews
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Home in Westport
Classic New England Home for 8 | Leafy Westport
4 bedrooms, 4 beds, 3 bathrooms
1–6 Oct
New place to stay
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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
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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, 228 reviews