228+ Hotel & Resort Deals in Windsor |
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Windsor Hotels, Resorts, and Rentals

About Windsor Vacation Rentals

There are more than 228 places to stay in Windsor that are available. These options include 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 places to stay in Windsor.

Are you seeking a last-minute 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 Hotala Windsor, you can quickly compare different options to find the hottest deals with a single click. Looking for 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 1085.58 ft² on average, with prices averaging US $377 a night.

Hotala 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 reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Windsor

Type Count
Vacation Homes 136
Holiday Apartments 26
Cabin Rentals 12
Cottages 11
Others 6
B&B 4
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windsor

★ Pro Tip: Hotala.co.nz has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay 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

Stay Near Windsor's Top Attractions

Hotala.co.nz can help you find hotels, resorts, and rentals near many of Windsor's top attractions, neighborhoods, and points of interest.


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 hotels or resorts in Windsor?

You have a lot of choices in or near Windsor. If you need a hotel in the Windsor area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Windsor:

How many vacation rentals have private pools in Windsor?

There are 8 accommodation options with private pools in or near Windsor. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 228 in the Windsor area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Windsor.


People Also Ask

There are 16 hotels in Windsor 6 resorts, and 174 rentals

Recently Booked Hotels, Resorts, or Rentals in Windsor