Family-friendly vacation rentals in Litchfield County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Litchfield County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Litchfield County family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Goshen
4.9 out of 5 average rating, 48 reviewsCharming renovated farmhouse with hot-tub
Sep 29 – Oct 6
Home in Litchfield
4.7 out of 5 average rating, 100 reviewsPrana Residence Spa Indoor Pool
Jan 30 – Feb 6
Home in Washington
4.79 out of 5 average rating, 19 reviewsZoomIn Map BestTown Washington "Kirby" PoshPadsCT
May 28 – Jun 4
Home in Sharon
4.72 out of 5 average rating, 18 reviews1700's Historical Home on Quiet 26 Acres w/ River
Mar 5 – 12
Home in Litchfield
4.95 out of 5 average rating, 88 reviewsHome in historic Litchfield village
Sep 6 – 13
Home in Washington
4.96 out of 5 average rating, 25 reviewsGlorious Washington Country Estate
Dec 18 – 25
Home in Warren
4.38 out of 5 average rating, 13 reviewsStrawberry Ridge Chalet with Hot Tub & Sauna!
Dec 31 – Jan 7
Home in Roxbury
5.0 out of 5 average rating, 8 reviewsZoom In Map Best Roxbury "Painter Hill" PoshPadsCT
Jun 11 – 18
Family- and pet-friendly home rentals
Home in Millerton
4.88 out of 5 average rating, 137 reviewsThe 1913 House, book 6 days get the 7th free.
Oct 25 – Nov 1
Cottage in New Fairfield
4.93 out of 5 average rating, 259 reviewsSweet Dotti's Cottage on Candlewood Lake - 60M NYC
Dec 15 – 22
Home in Warren
4.93 out of 5 average rating, 103 reviewsLitchfield County Getaway
Dec 27 – Jan 3
Home in New Milford
4.88 out of 5 average rating, 165 reviewsRenovated, one level home in an excellent location
Feb 4 – 11
Cabin in New Milford
4.82 out of 5 average rating, 116 reviewsA-Frame Cottage off Candlewood Lake
Sep 28 – Oct 5
Cottage in Litchfield
4.69 out of 5 average rating, 168 reviewsPaper Mill Cottage on the River
Jul 23 – 30
Cottage in Litchfield
4.99 out of 5 average rating, 77 reviewsThe House on the Hill
Jun 23 – 30
Home in Warren
4.94 out of 5 average rating, 98 reviewsBliss Cottage on Lake Waramug
Apr 26 – May 3
Family-friendly home rentals with a pool
Cottage in Litchfield
4.98 out of 5 average rating, 65 reviewsCottage on Litchfield Farm
Dec 23 – 30
Farm stay in Kent
4.77 out of 5 average rating, 305 reviewsThe Spirit Horse Farm in Kent, Ct.
Dec 24 – 31
Home in Sharon
5.0 out of 5 average rating, 35 reviewsCharming, peaceful cottage + magical view + pool
Cottage in New Milford
4.9 out of 5 average rating, 52 reviewsBUNTING HOUSE : CANDLEWOOD LAKEFRONT! 3BR CHALET
Jul 7 – 14
Home in Washington
4.75 out of 5 average rating, 20 reviewsFallen Fence 40 Private Acres Heated Pool & EVC!
Sep 26 – Oct 3
Home in Millerton
4.98 out of 5 average rating, 52 reviewsScandinavian Modern Upstate House w/Pool & Sauna
Jul 24 – 31
Home in Millerton
4.81 out of 5 average rating, 48 reviews1893 village farmhouse with pool
May 8 – 15
Home in Washington
4.96 out of 5 average rating, 24 reviewsSimply Serene: 5 ensuite bdrm and maximum coziness
Oct 8 – 15
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