Guesthouse vacation rentals in Litchfield County
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Top-rated guesthouses in Litchfield 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 Litchfield County guesthouses
Family-friendly guesthouses
Guesthouse in Barkhamsted
4.87 out of 5 average rating, 86 reviewsFarmington River Carriage House Pleasant Valley CT
Feb. 24 – Mar. 3
Guesthouse in Gaylordsville
4.98 out of 5 average rating, 91 reviewsAdorable Cottage in Pastoral Setting
Jan. 3 – 10
Guesthouse in New Milford
4.94 out of 5 average rating, 178 reviewsCharming Cottage w/Pastoral Views
Dec. 19 – 26
Guesthouse in Winchester
4.97 out of 5 average rating, 59 reviewsYear-round Lakefront Highland Lake - Immaculate
Feb. 16 – 23
Guesthouses with a patio
Guesthouse in New Fairfield
4.63 out of 5 average rating, 19 reviewsSquantz Cottage , Lakeview , w/ kayaks+firepit!
Dec. 12 – 19
Guesthouse in Millerton
5.0 out of 5 average rating, 4 reviewsThree Corner Farm
Mar. 15 – 22
Guesthouse in Cornwall
4.9 out of 5 average rating, 21 reviews1 bedroom pool house.
Sep. 14 – 21
Guesthouse in New Milford
Charming guest cottage
Nov. 1 – 8
Guesthouse in Cornwall
Lodge with pond on spectacular 300 acre estate
May 14 – 21
Guesthouse rentals with a washer and dryer
Guesthouse in Litchfield
5.0 out of 5 average rating, 7 reviewsLight and airy refurbished barn
Jan. 1 – 8
Guesthouse in Goshen
Sawmill House
Nov. 2 – 9
Guesthouse in New Milford
4.94 out of 5 average rating, 178 reviewsCharming Cottage w/Pastoral Views
Dec. 19 – 26
Guesthouse in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
Sep. 15 – 22
Guesthouse in Litchfield
5.0 out of 5 average rating, 15 reviewsBantam Woods Retreat - 2 bedrooms with queen beds
Aug. 6 – 13
Guesthouse in Litchfield
4.91 out of 5 average rating, 11 reviewsCozy remodeled Cottage
Apr. 10 – 17
Guesthouse in New Milford
5.0 out of 5 average rating, 43 reviewsLuxury in the Litchfield Hills
Mar. 15 – 22
Guesthouse in Gaylordsville
4.98 out of 5 average rating, 91 reviewsAdorable Cottage in Pastoral Setting
Jan. 3 – 10
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