233+ Pet Friendly Hotels and Vacation Rentals in Windsor |
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Windsor Pet Friendly Vacation Rentals

About Windsor Vacation Rentals

There are more than 233 places to stay in Windsor 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 Windsor.

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 Windsor, 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 Windsor. Places to stay near Windsor are 1066.03 ft² on average, with prices averaging US $383 a night.

PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Windsor 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 Windsor

Type Count
Vacation Homes 141
Holiday Apartments 27
Cottages 12

Use these Quick Filters to Find a Vacation Rental in Windsor

★ 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 Windsor.

Weather in Windsor, MA

View the weather forecast for Windsor 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 Windsor, MA

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


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
Beartown State Forest

Frequently Asked Questions About Windsor?

What are the top vacation rentals in Windsor?

Find the best options in or near Windsor for pet-friendly travel. If you are planning a trip or vacation in Windsor, 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 Windsor:

Which vacation homes in Windsor are best for families?

Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Windsor? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Windsor:

How many PetFriendly vacation rentals are available in Windsor?

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 233 in the Windsor 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 Windsor.


People Also Ask

There are 233 Windsor, MA Vacation Rentals

Recently Booked Pet Friendly Hotels and Vacation Rentals in Windsor