233+ Luxury Vacation Rentals & Cabins in Windsor |
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Windsor Cabin Rentals

About Windsor Vacation Rentals

There are more than 233 incredible getaway rentals that are available in Windsor. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Windsor.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Windsor, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Windsor. Places to stay near Windsor are 1066.03 ft² on average, with prices averaging CA $534 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Windsor. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals 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: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Windsor with Cabinns.ca.

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

Activities Windsor Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Windsor. Discover Top Attractions For Your Next Outdoor Adventure.


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 cabins, lake houses & summer homes in Windsor?

We provide an array of great vacation destinations in Windsor. If you are looking to stay in or around the Windsor area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windsor:

How many cabin rentals and resorts have private pools in Windsor?

We have 7 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Windsor. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Windsor is best for families?

Searching for a family-friendly cabin in Windsor? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Windsor?

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 233 in the Windsor area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Windsor.


People Also Ask

There are 14 hotels in Windsor 6 resorts, and 180 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Windsor