Pet-friendly holiday rentals in Berkshire County
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Top-rated pet-friendly home rentals in Berkshire County
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Berkshire County pet-friendly home rentals
Pet-friendly house rentals
Home in Lee
4.9 out of 5 average rating, 204 reviews1817 Berkshire Farmhouse- Close to Everything.
2–9 Sep
Home in Dalton
4.92 out of 5 average rating, 171 reviewsBrooksong, the perfect Berkshires getaway
23–30 Oct
Home in Lenox
4.93 out of 5 average rating, 209 reviewsHeart of Lenox Walk to Town Cozy Cottage!
14–21 Sep
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
26 Jan – 2 Feb
Home in Cheshire
4.86 out of 5 average rating, 199 reviews19th c. Barn in The Berkshires
12–19 Nov
Home in Egremont
4.96 out of 5 average rating, 105 reviewsThe Berkshires Mountain Terrace LUX Home Sleeps 7
16–23 Sep
Home in Williamstown
4.81 out of 5 average rating, 170 reviewsWalking distance to downtown
22–29 May
Home in New Marlborough
4.89 out of 5 average rating, 122 reviewsLake House in the Berkshire (Access Dock & Canoe
2–9 Oct
Pet-friendly home rentals with a pool
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
4–11 Dec
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
8–15 Jul
Guest suite in Great Barrington
5.0 out of 5 average rating, 45 reviewsSweet 1-bedroom with salt water pool
30 Sep – 7 Oct
Flat in Great Barrington
5.0 out of 5 average rating, 15 reviewsKing Bed | Stylish | Wi-Fi | *2m Ski Resort*
9–16 Mar
Home in Great Barrington
4.97 out of 5 average rating, 33 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
25 Jan – 1 Feb
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
14–21 Mar
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
26 Sep – 3 Oct
Cabin in Sand Lake
5.0 out of 5 average rating, 21 reviews"The Cabin" - Cozy & Rustic Home (Averill Park)
21–28 Dec
Private, pet-friendly home rentals
Guest house in North Adams
5.0 out of 5 average rating, 208 reviewsNetherwood - North Adams Guest House with Views
1–8 Oct
Flat in Great Barrington
4.93 out of 5 average rating, 179 reviewsSecluded but not isolated Berkshire Retreat
18–25 Sep
Cottage in Williamstown
4.9 out of 5 average rating, 165 reviewsCute Cozy Comfy Cottage in the Berkshires
20–27 Jul
Cabin in Canaan
4.98 out of 5 average rating, 132 reviewsNewly Renovated Cabin in the Country
23–30 Jul
Cottage in Lanesborough
4.85 out of 5 average rating, 250 reviewsWildlife Lakeside Cottage
14–21 Feb
Cabin in Lee
4.9 out of 5 average rating, 102 reviewsSpring sale! Cabin with views in the Berkshires
19–26 Nov
Cabin in North Adams
4.93 out of 5 average rating, 143 reviewsThe Wampanoag Cabin @ The Wigwam Western Summit
27 Jul – 3 Aug
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
16–23 Dec
Destinations to explore
- Pet-friendly rentals New York
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