Family-friendly holiday rentals in Lenox
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Lenox
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 Lenox family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
14–21 Oct
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
24–31 Dec
Cabin in Saugerties
4.86 out of 5 average rating, 172 reviewsContainer Cabin in the Catskills (Field)
18–25 Oct
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
9–16 Oct
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
21–28 Jul
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
19–26 Mar
Home in Round Top
4.96 out of 5 average rating, 161 reviewsEscape in the Catskills w/hottub
22–29 Jun
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
28 Oct – 4 Nov
Family- and pet-friendly home rentals
Home in West Stockbridge
4.87 out of 5 average rating, 102 reviewsPeaceful Stockbridge Cabin in the Woods
11–18 May
Flat in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
13–20 Sept
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
31 Oct – 7 Nov
Cottage in Claverack
4.98 out of 5 average rating, 244 reviews‘Clavashack’ Country Cottage
2–7 May
Cottage in Lanesborough
4.85 out of 5 average rating, 251 reviewsWildlife Lakeside Cottage
6–13 Feb
Guest suite in Charlemont
4.9 out of 5 average rating, 182 reviewsUnique People & Pet-Welcoming Haven
7–14 Mar
Flat in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
20–27 Dec
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
28 Sept – 5 Oct
Family-friendly home rentals with a pool
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
16–23 Jun
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
23–30 Jan
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
24 Nov – 1 Dec
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
8–15 Oct
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sept
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
13–20 Jan
Flat in Rexford
4.96 out of 5 average rating, 324 reviewsNeed a Getaway??
20–27 Apr
Flat in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
11–18 Oct
Quick stats about holiday rentals that are family-friendly in Lenox
Total rentals
100 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Total number of reviews
3.7K reviews
Nightly prices starting at
£80 before taxes and fees
Destinations to explore
- New City Holiday rentals
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