Guesthouse vacation rentals in Litchfield County
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Top-rated guesthouse rentals in Litchfield County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Litchfield County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Barkhamsted
4.87 out of 5 average rating, 86 reviewsFarmington River Carriage House Pleasant Valley CT
Jan 22 – 29
Guesthouse in Wolcott
5.0 out of 5 average rating, 4 reviewsGallagher Village Lakefront Cottage - EV Friendly
May 28 – Jun 4
Guesthouse in Gaylordsville
4.98 out of 5 average rating, 91 reviewsAdorable Cottage in Pastoral Setting
Feb 7 – 14
Guesthouse in New Milford
4.94 out of 5 average rating, 178 reviewsCharming Cottage w/Pastoral Views
Dec 31 – Jan 7
Guesthouse in Winchester
4.97 out of 5 average rating, 59 reviewsYear-round Lakefront Highland Lake - Immaculate
Feb 19 – 26
Guest house rentals with a patio
Guesthouse in New Fairfield
4.65 out of 5 average rating, 20 reviewsSquantz Cottage , Lakeview , w/ kayaks+firepit!
Nov 30 – Dec 7
Guesthouse in Millerton
5.0 out of 5 average rating, 4 reviewsThree Corner Farm
Oct 4 – 11
Guesthouse in Cornwall
4.9 out of 5 average rating, 21 reviews1 bedroom pool house.
Sep 28 – Oct 5
Guesthouse in New Milford
Charming guest cottage
Nov 4 – 11
Guesthouse in Cornwall
Lodge with pond on spectacular 300 acre estate
May 14 – 21
Guest house rentals with a washer and dryer
Guesthouse in Litchfield
5.0 out of 5 average rating, 7 reviewsLight and airy refurbished barn
Jan 10 – 17
Guesthouse in Goshen
Sawmill House
Sep 27 – Oct 4
Guesthouse in New Milford
4.94 out of 5 average rating, 178 reviewsCharming Cottage w/Pastoral Views
Dec 31 – Jan 7
Guesthouse in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
Aug 21 – 28
Guesthouse in Litchfield
5.0 out of 5 average rating, 15 reviewsBantam Woods Retreat - 2 bedrooms with queen beds
Jan 1 – 8
Guesthouse in Litchfield
4.91 out of 5 average rating, 11 reviewsCozy remodeled Cottage
Oct 22 – 29
Guesthouse in New Milford
5.0 out of 5 average rating, 43 reviewsLuxury in the Litchfield Hills
Nov 26 – Dec 3
Guesthouse in Gaylordsville
4.98 out of 5 average rating, 91 reviewsAdorable Cottage in Pastoral Setting
Feb 7 – 14
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