Family-friendly holiday rentals in Litchfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Litchfield
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Litchfield family-friendly rentals
Family-friendly home rentals with a hot tub
Farm stay in Kent
4.87 out of 5 average rating, 263 reviews(°) The Wandering Peacock (°)
9–16 Jan
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
30 Mar – 6 Apr
Bungalow in Easthampton
4.92 out of 5 average rating, 433 reviewsThe Creation Station
26 Jul – 2 Aug
Home in Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
2–9 Aug
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
14–21 Dec
Home in Red Hook
4.88 out of 5 average rating, 212 reviewsWooded Retreat w/ Hot Tub and Trout River
5–12 Nov
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
6–13 Aug
Home in Rhinebeck
4.9 out of 5 average rating, 206 reviewsRhinebeck Modern Home with amazing outdoor space
25 Feb – 4 Mar
Family- and pet-friendly home rentals
Guest suite in Goshen
4.75 out of 5 average rating, 216 reviewsRural Litchfield County Apartment Goshen CT
12–19 Dec
Guesthouse in New Milford
4.94 out of 5 average rating, 178 reviewsCharming Cottage w/Pastoral Views
21–28 Apr
Cottage in Red Hook
4.98 out of 5 average rating, 599 reviewsbright serene + spacious barn
11–18 Sep
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
31 Mar – 7 Apr
Cottage in Middlefield
4.93 out of 5 average rating, 230 reviewsLake Beseck cottage
30 Nov – 7 Dec
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
17–24 Feb
Home in Feeding Hills
4.89 out of 5 average rating, 886 reviewsFarm Fresh Feeding Hills
17–24 Oct
Cottage in Claverack
4.98 out of 5 average rating, 245 reviews‘Clavashack’ Country Cottage
18–23 Aug
Family-friendly home rentals with a pool
Apartment in Glastonbury
4.9 out of 5 average rating, 409 reviewsQuiet 2 bed room apt w/ private entrance.
16–23 Feb
Barn in Bethel
4.98 out of 5 average rating, 203 reviewsEscape to a Restored New England Antique Milk Barn
12–19 Feb
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
22–29 Aug
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
5–12 Nov
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
28 Dec – 4 Jan
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
2–9 Oct
Townhouse in Hudson
4.94 out of 5 average rating, 194 reviewsPalazzo Hudson: Luxury Pool, Hot Tub, and Sauna
16–23 Mar
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
22–29 Oct
Quick stats about holiday rentals that are family-friendly in Litchfield
Total rentals
100 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
40 properties allow pets
Total number of reviews
3.6K reviews
Nightly prices starting at
$150 NZD before taxes and fees
Destinations to explore
- Family-friendly rentals New York
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