Book Windsor hotels

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Check hotel availability in Windsor

Cheap Windsor hotels

Hotel Downstreet

Hotel Downstreet

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is NZ$278 per night from 10 Jul to 11 Jul
NZ$278
per night
10 Jul - 11 Jul
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our ...
Hotel Downstreet
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$248 per night from 8 Jul to 9 Jul
NZ$248
per night
8 Jul - 9 Jul
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Life House Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is NZ$262 per night from 10 Jul to 11 Jul
NZ$262
per night
10 Jul - 11 Jul
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Yankee, Trademark Collection by Wyndham
Save an average of 15% on thousands of hotels when you're signed in
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
The price is NZ$355 per night from 9 Jul to 10 Jul
NZ$355
per night
9 Jul - 10 Jul
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is NZ$466 per night from 8 Jul to 9 Jul
NZ$466
per night
8 Jul - 9 Jul
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the pool and the restaurant in our ...
The Red Lion Inn
The Lenox Collection

The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is NZ$202 per night from 9 Jul to 10 Jul
NZ$202
per night
9 Jul - 10 Jul
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Lenox Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
The price is NZ$347 per night from 1 Jul to 2 Jul
NZ$347
per night
1 Jul - 2 Jul
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the clean ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$231 per night from 10 Jul to 11 Jul
NZ$231
per night
10 Jul - 11 Jul
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Quality Inn
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is NZ$265 per night from 10 Jul to 11 Jul
NZ$265
per night
10 Jul - 11 Jul
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Don't see what you're looking for?
See all available properties in Windsor
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Windsor

Although there's very few accommodation options within Windsor itself, we do offer a great range of options in the wider area. There's around 73 hotels that are situated within a 30-kilometre radius of Windsor.

Keen on accommodation close to Windsor? Check out the Rookwood Inn, located 25 kilometres away in Massachusetts. If those options don't float your boat, check out the Gateways Inn & Restaurant in Massachusetts.

You could also check out the Hampton Terrace Inn as well as the Cranwell Spa and Golf Resort. The Hampton Terrace Inn can be found 25 kilometres away from the heart of Windsor. The Cranwell Spa and Golf Resort is situated 25 kilometres away. Some other hotels include the Birchwood Inn and the Wyndham Bentley Brook.

Don't be a flamin' galah and farewell Windsor without exploring the other great things to do and places to explore in Western Massachusetts. Explore the history museums in Western Massachusetts. You can also make the time to check out the region's mountains and rolling hills. Visitors and locals alike in this part of United States of America can also enjoy skiing and cross-country skiing.

Don't shoot through before you have checked out the Williams College and Williams College Museum of Art in Williamstown. Some of our recommended Williamstown hotels and accommodations are the The Spring's Inn and Berkshire Hills Country Inn. Or, you could consider staying in Lee, 30 kilometres to the southwest of Windsor, where you'll find the Black Swan Inn, an Ascend Collection Hotel and Chambery Inn. The Lee Prime Outlets and Tyringham Cobble are amongst the more popular sites to check out in Lee.

Aussies are known internationally for their passion for sport, so why not visit Times Union Center? Discover Times Union Center 60 kilometres to the west of Windsor. For tourists who are keen on sleeping close by, make a reservation at the Hilton Albany or the TownePlace Suites by Marriott Albany Downtown/Medical Center.

Albany International Airport is situated 65 kilometres away from the centre of Windsor. Should you choose to stay nearby, you can easily book a night at the Residence Inn by Marriott Albany Airport or the The Desmond Hotel and Conference Center.

Windsor hotels essential information

Accommodation
858 hotels
Lowest Price
NZ$202
Highest Price
NZ$466
Popular hotels
Hotel Downstreet, Life House Berkshires, The Yankee, Trademark Collection by Wyndham, The Black Swan Lee - Lenox, Ascend Hotel Collection, The Red Lion Inn, The Lenox Collection, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, Quality Inn, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Most recent Windsor hotel reviews

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.