Family-friendly vacation 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.
Vacation 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
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 7 – 14
Farm stay in Kent
4.87 out of 5 average rating, 263 reviews(°) The Wandering Peacock (°)
Jan 8 – 15
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
Oct 16 – 23
Bungalow in Easthampton
4.92 out of 5 average rating, 433 reviewsThe Creation Station
Jul 23 – 30
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Mar 13 – 20
Home in Highland
4.96 out of 5 average rating, 108 reviewsHouse in Highland: Secluded Retreat
Nov 3 – 10
Home in Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
Sep 21 – 28
Home in Red Hook
4.88 out of 5 average rating, 212 reviewsWooded Retreat w/ Hot Tub and Trout River
Nov 4 – 11
Family- and pet-friendly home rentals
Guesthouse in New Milford
4.94 out of 5 average rating, 178 reviewsCharming Cottage w/Pastoral Views
Apr 21 – 28
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Feb 19 – 26
Cottage in Middlefield
4.93 out of 5 average rating, 230 reviewsLake Beseck cottage
Aug 11 – 18
Home in Feeding Hills
4.89 out of 5 average rating, 886 reviewsFarm Fresh Feeding Hills
Sep 1 – 8
Cottage in Craryville
4.91 out of 5 average rating, 482 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Nov 5 – 12
Cottage in Red Hook
4.98 out of 5 average rating, 599 reviewsbright serene + spacious barn
Dec 10 – 17
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
Aug 18 – 23
Cottage in Putnam Valley
4.9 out of 5 average rating, 215 reviewsLakefront Cottage near Hudson Valley
Dec 8 – 15
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.
Dec 19 – 26
Cabin in Red Hook
4.96 out of 5 average rating, 306 reviewsModern Upstate Cabin, near Rhinebeck NY
Aug 22 – 29
Barn in Bethel
4.98 out of 5 average rating, 203 reviewsEscape to a Restored New England Antique Milk Barn
Dec 29 – Jan 5
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Dec 27 – Jan 3
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Dec 14 – 21
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
Oct 1 – 8
Farm stay in Rhinebeck
4.94 out of 5 average rating, 172 reviewsMajestic Oasis in Rhinebeck w/ Hot Tub & Pool
Jan 2 – 9
Quick stats about vacation 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
$90 before taxes and fees
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Montauk Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Family-friendly rentals New York
- Family-friendly rentals United States
- Family-friendly rentals Manhattan
- Family-friendly rentals Brooklyn
- Family-friendly rentals Connecticut
- Rentals with pools Litchfield
- Waterfront rentals Litchfield
- Kid-friendly rentals Litchfield
- House rentals Litchfield
- Rentals with a washer and dryer Litchfield
- Monthly Rentals Litchfield
- Rentals with a fire pit Litchfield
- Rentals with lake access Litchfield
- Rentals with a patio Litchfield
- Rentals with a fireplace Litchfield
- Fitness-friendly rentals Litchfield
- Rentals with beach access Litchfield
- Rentals with outdoor seating Litchfield
- Pet-friendly rentals Litchfield
- Family-friendly rentals Litchfield County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes