232+ Rental Villas and Private Getaways in Windsor |
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Windsor Vacation Rentals & One Degree Stays Homes

About Windsor Vacation Rentals

There are more than 232 vacation rentals that are available in Windsor. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Windsor.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Windsor, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Windsor. Places to stay near Windsor are 1066.31 ft² on average, with prices averaging US $384 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Windsor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Windsor

Type Count
Vacation Homes 141
Holiday Apartments 26
Cottages 12

Use these Quick Filters to Find a Vacation Rental in Windsor

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor.

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

OneDegreeStays 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?

There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor:

How many vacation rentals have private pools in Windsor?

There are 5 vacation rentals with private pools near Windsor. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Windsor are best for families?

If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:

How many onedegreestays vacation rentals are available in Windsor?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 232 in the Windsor area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Windsor. 


People Also Ask

There are 232 Windsor, MA Vacation Rentals

Recently Booked Vacation Rentals in Windsor