
Pet-friendly holiday rentals in Chester
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chester
Guests agree: these pet-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 Chester pet-friendly home rentals
Pet-friendly house rentals

2 Doors Down - Modern Farmhouse in Downtown Ludlow

Cozy Contemporary Downtown Texaco

Modern 3-bedroom A-frame in Londonderry w/ Pond

The Grafton Chateau

Wild Blossom Farmhouse - a lovely family getaway

Stylish Ascutney Cabin with Mountain Views

Cozy Home in Poultney, Vermont.

Meadow View. 35 acres outside your door!
Pet-friendly home rentals with a pool

"Mountain View" Rustic Cabin Retreat w/Fireplace

Ranch at Mendon Mt Orchards

The Brick House on Washington Street

SKI ON/OFF Spruce Glen C | AC | Sauna| Fireplace

Cozy Vermont Antique Sugar House with Fireplace

Historic Home on 17 acres of land. Go escape!

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Private, pet-friendly home rentals

Sage House at Camp Greenwood Vermont with Sauna

Guest House at Hummingbird Hill

HeART Barn Retreat

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit

Boulder House - Extraordinary Luxury in the Woods!

The Studio With a View. Bring your dog, too!

Lighthouse Inn the Woods~peaceful nature escape

Chester Mountain View
Quick stats about holiday rentals that are pet-friendly in Chester
Total rentals
20 properties
Nightly prices starting at
₹7,929 before taxes and fees
Total number of reviews
790 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
- Plainview Holiday rentals
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- Rentals with a washing machine and dryer Chester
- Rentals with a patio Chester
- Rentals with a fireplace Chester
- Rentals with a firepit Chester
- House rentals Chester
- Rentals with outdoor seating Chester
- Family-friendly rentals Chester
- Pet-friendly rentals Windsor County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Dartmouth Skiway
- Ragged Mountain Resort
- Stratton Mountain Resort
- Dorset Field Club
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Hooper Golf Course
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Crotched Mountain Ski and Ride
- Lucky Bugger Vineyard & Winery
- Ekwanok Country Club
- Fox Run Golf Club
- Montshire Museum of Science
- Autumn Mountain Winery
- Whaleback Mountain
- Baker Hill Golf Club
- Mount Sunapee Resort