233+ Vacation Home Rentals in Windsor |
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  3. Windsor

Windsor Vacation Rentals & Ski-in/Ski-out Homes

About Windsor Vacation Rentals

Explore over 233 vacation rentals in Windsor with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Windsor for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Windsor. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Windsor tailored to your preferences. On average, these rentals offer 1066.03 ft² of space, and are priced at an average of US $383 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Windsor at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Windsor

Type Count
Vacation Homes 141
Holiday Apartments 27
Cabin Rentals 12
Cottages 12
Others 6
B&B 4
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windsor

★ Pro Tip: Discover Your Ideal Vacation Rental in Windsor with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in Windsor, MA

View the weather forecast for Windsor before booking your Windsor Vacation Rentals to confirm your best time to go.

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

Top Attractions Around Windsor, MA

Sunski offers a large selection of top attractions around Windsor . Research things to do on your vacation before you visit Windsor.


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?

When organizing your trip to Windsor, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Windsor. Peruse our collection of highly-rated properties and secure your reservation today.

How many vacation rentals have private pools in Windsor?

Uncover 6 vacation rentals boasting private pools near Windsor. Explore top-rated RBO homes offering access to a swimming pool:

Which vacation homes or resorts in Windsor are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Windsor. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Windsor?

Discover the ideal vacation rental in Windsor with SunSki Resorts™. We provide an extensive selection of over 233 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Windsor.


People Also Ask

There are 233 Windsor, MA Vacation Rentals

Recently Booked Vacation Rentals in Windsor