Guesthouse vacation rentals in Fairfield County
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Top-rated guesthouses in Fairfield County
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Fairfield County guesthouses
Family-friendly guesthouses
Guesthouse in Milford
4.92 out of 5 average rating, 191 reviewsSilversands Air-Bnb You’re right Here!
Mar. 2 – 9
Guesthouse in Norwalk
5.0 out of 5 average rating, 18 reviewsGuest Cottage in Rowayton
Oct. 25 – Nov. 1
Guesthouse in Norwalk
5.0 out of 5 average rating, 58 reviewsCottage by the Sea
Oct. 8 – 15
Guesthouse in Gaylordsville
4.98 out of 5 average rating, 91 reviewsAdorable Cottage in Pastoral Setting
Feb. 27 – Mar. 6
Guesthouses with a patio
Guesthouse in Wilton
5.0 out of 5 average rating, 22 reviewsThe Ciderhouse Cottage - private escape in Wilton
Nov. 9 – 16
Guesthouse in New Milford
5.0 out of 5 average rating, 43 reviewsLuxury in the Litchfield Hills
May 19 – 26
Guesthouse in Waccabuc
4.97 out of 5 average rating, 33 reviewsFrench Guest House in Waccabuc
Jun. 11 – 18
Guesthouse in Redding
4.97 out of 5 average rating, 30 reviewsThe Cottage in Redding
Jan. 8 – 15
Guesthouse in Weston
5.0 out of 5 average rating, 51 reviewsAdorable 1-Bedroom Cottage w/ Mezzanine Weston, CT
Apr. 3 – 10
Guesthouse in North Castle
4.98 out of 5 average rating, 43 reviewsMagical 1700's 1 bedroom cottage
Jul. 17 – 24
Guesthouse in Brewster
4.94 out of 5 average rating, 99 reviewsSherwood Barn - close to ski mountain
Oct. 7 – 14
Guesthouse in Pound Ridge
5.0 out of 5 average rating, 14 reviewsRenovated guesthouse on private 7 acre property
Dec. 24 – 31
Guesthouse rentals with a washer and dryer
Guesthouse in South Salem
5.0 out of 5 average rating, 66 reviewsNewly renovated guesthouse with a patio
Jul. 11 – 18
Guesthouse in Katonah
4.94 out of 5 average rating, 81 reviewsAdorable one bedroom guesthouse
Apr. 24 – May 1
Guesthouse in Setauket- East Setauket
4.85 out of 5 average rating, 135 reviewsNewly Renovated Water Front Cottage in Setauket
Jan. 15 – 22
Guesthouse in Pound Ridge
4.8 out of 5 average rating, 15 reviewsPound Ridge Cottage
Sep. 28 – Oct. 5
Guesthouse in Norwalk
5.0 out of 5 average rating, 9 reviews1-Bedroom Guest Cottage
Sep. 25 – Oct. 2
Guesthouse in Bedford
5.0 out of 5 average rating, 13 reviewsRed Coat Cottage
Jul. 3 – 10
Guesthouse in Easton
4.84 out of 5 average rating, 95 reviewsEntire Guest House at Fox Pond Farm.
Sep. 29 – Oct. 6
Guesthouse in Greenwich
5.0 out of 5 average rating, 5 reviewsCottage Escape! Country Retreat!
Oct. 16 – 23
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