Family-friendly holiday rentals in Dutchess County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Dutchess 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 Dutchess County family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Red Hook
4.88 out of 5 average rating, 212 reviewsWooded Retreat w/ Hot Tub and Trout River
24 Sept – 1 Oct
Farm stay in Kent
4.87 out of 5 average rating, 263 reviews(°) The Wandering Peacock (°)
13–20 Nov
Home in Rhinebeck
4.9 out of 5 average rating, 206 reviewsRhinebeck Modern Home with amazing outdoor space
4–11 May
Guest house in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
5–12 May
Home in Beacon
4.96 out of 5 average rating, 308 reviewsRiver & Mtn Views - Jacuzzi - near Metro North
20–27 Apr
Home in Ancramdale
4.93 out of 5 average rating, 127 reviewsSki & unwind in the country, stargaze in hot tub
5–12 Aug
Farm stay in Rhinebeck
4.94 out of 5 average rating, 172 reviewsMajestic Oasis in Rhinebeck w/ Hot Tub & Pool
19–26 Jan
Villa in Hopewell Junction
4.96 out of 5 average rating, 279 reviewsThe Mission House Sanctuary
22–29 Apr
Family- and pet-friendly home rentals
Flat in Saugerties
4.91 out of 5 average rating, 171 reviewsEsopus Bend Getaway - 4 min to HITS
15–22 May
Home in Rhinebeck
4.84 out of 5 average rating, 238 reviewsPrivate Lakefront Bungalow
16–23 May
Home in Millbrook
4.9 out of 5 average rating, 139 reviewsSerene Waterfront Mill House, Stroll to Village
21–28 Feb
Home in Millerton
4.93 out of 5 average rating, 366 reviewsMountaintop Skyloft
24–31 Aug
Home in Poughquag
4.98 out of 5 average rating, 132 reviewsThe Beekman Salt Box - 1860 Hudson Valley Home
27 May – 3 Jun
Home in Millerton
4.88 out of 5 average rating, 137 reviewsThe 1913 House, book 6 days get the 7th free.
19–26 Oct
Campervan/Motorhome in Wappingers Falls
4.89 out of 5 average rating, 186 reviewsCamping(Pebble base camp) private campsite
4–11 May
Home in Rhinebeck
4.86 out of 5 average rating, 189 reviewsVibrant Vintage Country House with Backyard
28 Jun – 5 Jul
Family-friendly home rentals with a pool
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
22–29 Sept
Home in Lagrangeville
5.0 out of 5 average rating, 21 reviewsHudson Valley Colonial with Inground Pool
18–25 Apr
Home in Lagrangeville
5.0 out of 5 average rating, 11 reviewsA-Frame w/ 3 Bedrooms, 2 Full Baths, Swimming Pond
19–26 Jun
Home in Saugerties
4.91 out of 5 average rating, 94 reviewsPeaceful Hudson Valley Getaway
12–19 May
Home in Barrytown
4.84 out of 5 average rating, 19 reviewsGorgeous 4 BR-4BR House and Pool/ Unique Location
2–9 May
Home in Saugerties
5.0 out of 5 average rating, 92 reviewsSaugerties Luxury Rental, Close to Skiing
3–10 Aug
Cottage in Dover Plains
5.0 out of 5 average rating, 12 reviewsCharming Country House
11–18 Nov
Home in Clinton Corners
4.94 out of 5 average rating, 17 reviewsGorgeous Hudson Valley Farmhouse with heated pool
6–13 Nov
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