Family-friendly holiday rentals in Lewisboro
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Lewisboro
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 Lewisboro family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Cold Spring
4.95 out of 5 average rating, 282 reviewsHilltop Hideaway Forest Villa on 13 acres!
15–22 Feb
Home in Tomkins Cove
4.94 out of 5 average rating, 137 reviewsHudson Valley Victorian with River Views
28 Jan – 4 Feb
Flat in New Paltz
4.97 out of 5 average rating, 467 reviewsRelaxing Spa Retreat~Gorgeous View~Walk to Village
11–18 Jan
Guest house in Beacon
4.94 out of 5 average rating, 367 reviewsCozy Mountainside Suite - Minutes from Beacon
2–9 Mar
Farm stay in Kent
4.87 out of 5 average rating, 264 reviews(°) The Wandering Peacock (°)
9–16 Feb
Home in Highland
4.96 out of 5 average rating, 108 reviewsHouse in Highland: Secluded Retreat
30 Sep – 7 Oct
Guest suite in Patchogue
4.93 out of 5 average rating, 269 reviewsShores Retreat Suite - Peaceful Relaxation
21–26 Jun
Guest suite in New Paltz
4.95 out of 5 average rating, 327 reviewsMajestic Studio with Shawangunk Mountain Views
3–10 Jun
Family- and pet-friendly home rentals
Flat in Carmel
4.87 out of 5 average rating, 275 reviewsPrivate space, with yard
26 Oct – 2 Nov
Guest house in Fairfield
4.96 out of 5 average rating, 173 reviewsSouthport, CT across from BEACH
29 Apr – 6 May
Guest suite in Cold Spring
4.79 out of 5 average rating, 484 reviewsCozy getaway in Cold Spring
8–15 Dec
Guest suite in Fort Montgomery
4.94 out of 5 average rating, 420 reviewsWest Point - Mountain Top Suite
7–14 Jun
Farm stay in High Falls
4.87 out of 5 average rating, 809 reviewsDave's Milk Barn
23–30 Oct
Farm stay in West Simsbury
4.95 out of 5 average rating, 434 reviewsFlamig Farm Staycation
25 Mar – 1 Apr
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
29 Dec – 5 Jan
Home in Fairfield
4.96 out of 5 average rating, 291 reviewsLuxurious Barn With New England Charm
11–18 Dec
Family-friendly home rentals with a pool
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
3–10 Sep
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
31 Oct – 7 Nov
Guest suite in New Paltz
4.84 out of 5 average rating, 181 reviewsPrivate apartment in rural home
19–26 Mar
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
15–22 Jul
Home in Litchfield
4.93 out of 5 average rating, 165 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
4–11 Sep
Flat in Union
4.89 out of 5 average rating, 228 reviewsSparkling Clean | Onsite Team | Business Amenities
1–8 Jan
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
18–25 Sep
Cottage in West Orange
4.87 out of 5 average rating, 189 reviewsCozy Pool Cottage
9–16 Oct
Quick stats about holiday rentals that are family-friendly in Lewisboro
Total rentals
80 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
30 properties allow pets
Total number of reviews
1.4K reviews
Nightly prices starting at
$122 SGD before taxes and fees
Destinations to explore
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