Family-friendly holiday houses in Litchfield County
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Top-rated family-friendly rentals in Litchfield County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday 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
29 Nov – 6 Dec
Home in Litchfield
4.7 out of 5 average rating, 100 reviewsPrana Residence Spa Indoor Pool
29 Jan – 5 Feb
Home in Washington
4.79 out of 5 average rating, 19 reviewsZoomIn Map BestTown Washington "Kirby" PoshPadsCT
16 – 23 May
Home in Sharon
4.72 out of 5 average rating, 18 reviews1700's Historical Home on Quiet 26 Acres w/ River
4 – 11 Mar
Home in Litchfield
4.95 out of 5 average rating, 88 reviewsHome in historic Litchfield village
4 – 11 Jan
Home in Washington
4.96 out of 5 average rating, 25 reviewsGlorious Washington Country Estate
12 – 19 July
Home in Warren
4.38 out of 5 average rating, 13 reviewsStrawberry Ridge Chalet with Hot Tub & Sauna!
30 Dec – 6 Jan
Home in Roxbury
5.0 out of 5 average rating, 8 reviewsZoom In Map Best Roxbury "Painter Hill" PoshPadsCT
23 – 30 June
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.
24 – 31 Oct
Cottage in New Fairfield
4.93 out of 5 average rating, 259 reviewsSweet Dotti's Cottage on Candlewood Lake - 60M NYC
1 – 8 Dec
Home in Warren
4.93 out of 5 average rating, 103 reviewsLitchfield County Getaway
14 – 21 Oct
Home in New Milford
4.88 out of 5 average rating, 165 reviewsRenovated, one level home in an excellent location
16 – 23 Apr
Cabin in New Milford
4.82 out of 5 average rating, 116 reviewsA-Frame Cottage off Candlewood Lake
28 Sept – 5 Oct
Cottage in Litchfield
4.69 out of 5 average rating, 168 reviewsPaper Mill Cottage on the River
22 – 29 Jan
Cottage in Litchfield
4.99 out of 5 average rating, 77 reviewsThe House on the Hill
6 – 13 May
Home in Warren
4.94 out of 5 average rating, 98 reviewsBliss Cottage on Lake Waramug
25 Apr – 2 May
Family-friendly home rentals with a pool
Cottage in Litchfield
4.98 out of 5 average rating, 65 reviewsCottage on Litchfield Farm
22 – 29 Dec
Farm stay in Kent
4.77 out of 5 average rating, 305 reviewsThe Spirit Horse Farm in Kent, Ct.
25 June – 2 July
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
10 – 17 Jan
Home in Washington
4.75 out of 5 average rating, 20 reviewsFallen Fence 40 Private Acres Heated Pool!
8 – 15 Jan
Home in Millerton
4.98 out of 5 average rating, 52 reviewsScandinavian Modern Upstate House w/Pool & Sauna
24 – 31 July
Home in Washington
4.96 out of 5 average rating, 24 reviewsSimply Serene: 5 ensuite bdrm and maximum coziness
7 – 14 Oct
Home in Millerton
4.81 out of 5 average rating, 48 reviews1893 village farmhouse with pool
7 – 14 May
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