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Cheap Windsor hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is NZ$219 per night from 15 Dec to 16 Dec
NZ$219
15 Dec - 16 Dec
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
Opens in a new windowVacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 15 Dec to 16 Dec
NZ$379
15 Dec - 16 Dec
includes taxes & fees
Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Williams Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is NZ$178 per night from 16 Dec to 17 Dec
NZ$178
16 Dec - 17 Dec
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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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$144 per night from 24 Dec to 25 Dec
NZ$144
24 Dec - 25 Dec
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is NZ$228 per night from 8 Jan to 9 Jan
NZ$228
8 Jan - 9 Jan 2026
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowBerkshire Mountain Lodge
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$365 per night from 14 Jan to 15 Jan
NZ$365
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this historic hotel in Stockbridge. Enjoy free Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Red Lion Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$211 per night from 15 Dec to 16 Dec
NZ$211
15 Dec - 16 Dec
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowBerkshires Untold
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Fully refundableReserve now, pay when you stay
The price is NZ$266 per night from 17 Dec to 18 Dec
NZ$266
17 Dec - 18 Dec
includes taxes & fees
Stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business centre and a snack bar/deli. Our guests praise the helpful staff in their ...
Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd South Deerfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$171 per night from 17 Dec to 18 Dec
NZ$171
17 Dec - 18 Dec
includes taxes & fees
Stay at this hotel in South Deerfield. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowRed Roof Inn PLUS+ South Deerfield – Amherst
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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
973 hotels
Lowest Price
NZ$144
Highest Price
NZ$379
Popular hotels
Vacation Village in the Berkshires, The Williams Inn, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Berkshire Mountain Lodge, The Red Lion Inn, Berkshires Untold, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Red Roof Inn PLUS+ South Deerfield – Amherst

Most recent Windsor hotel reviews

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^Subject to availability and chosen travel dates.