59+ Pet Friendly Hotels and Vacation Rentals in Cheshire |
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Cheshire Pet Friendly Vacation Rentals

About Cheshire Vacation Rentals

There are more than 59 places to stay in Cheshire and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in Cheshire.

Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly Cheshire, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Cheshire. Places to stay near Cheshire are 877.43 ft² on average, with prices averaging US $349 a night.

PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Cheshire with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.

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Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Cheshire

Type Count
Vacation Homes 36
Holiday Apartments 10
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Cheshire

★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Cheshire.

Weather in Cheshire, MA

View the weather forecast for Cheshire before booking your hotel or rental.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Cheshire, MA

PetFriendly finds and compares Pet-Friendly hotels, rentals, and resort listings near many of Cheshire's attractions.


St Mary's of the Assumption Church
Jiminy Peak Mountain Resort
Tanglewood Music Center
Mass MoCA
Williams College
Berkshire East Ski Resort
Norman Rockwell Museum
National Shrine of the Divine Mercy
Mohawk Trail State Forest
Lee Prime Outlets
Bousquet Ski Area
Mount Greylock
Williamstown Theatre Festival
Cranwell Golf Club
Jacob's Pillow
Berkshire Museum
Bridge of Flowers
Hancock Shaker Village
Pittsfield State Forest
October Mountain State Forest

Other Places to Stay in Cheshire, MA


St Mary's of the Assumption Church 54 Properties

Frequently Asked Questions About Cheshire?

What are the top vacation rentals in Cheshire?

Find the best options in or near Cheshire for pet-friendly travel. If you are planning a trip or vacation in Cheshire, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Cheshire:

How many PetFriendly vacation rentals are available in Cheshire?

PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2025 is over 59 in the Cheshire area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Cheshire.


People Also Ask

There are 59 Cheshire, MA Vacation Rentals

Recently Booked Pet Friendly Hotels and Vacation Rentals in Cheshire