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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 AU$191 per night from 15 Dec to 16 Dec
AU$191
15 Dec - 16 Dec
includes taxes & fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
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 AU$331 per night from 15 Dec to 16 Dec
AU$331
15 Dec - 16 Dec
includes taxes & fees
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
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 AU$156 per night from 16 Dec to 17 Dec
AU$156
16 Dec - 17 Dec
includes taxes & fees
With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center ...
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 AU$126 per night from 24 Dec to 25 Dec
AU$126
24 Dec - 25 Dec
includes taxes & fees
Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
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 AU$199 per night from 8 Jan to 9 Jan
AU$199
8 Jan - 9 Jan 2026
includes taxes & fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
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 AU$319 per night from 14 Jan to 15 Jan
AU$319
14 Jan - 15 Jan 2026
includes taxes & fees
With a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Housatonic ...
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 AU$184 per night from 15 Dec to 16 Dec
AU$184
15 Dec - 16 Dec
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
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 AU$232 per night from 17 Dec to 18 Dec
AU$232
17 Dec - 18 Dec
includes taxes & fees
With a stay at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood ...
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 AU$150 per night from 17 Dec to 18 Dec
AU$150
17 Dec - 18 Dec
includes taxes & fees
With a stay at Red Roof Inn PLUS+ South Deerfield – Amherst in South Deerfield, you'll be within a 15-minute drive of University of Massachusetts Amherst and ...
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

Searching for a hotel in Windsor? Unfortunately, they're as rare as the hair on your great uncle Alan's head. But you'll have plenty of choice if you drive just outside of town. Take your pick of 67 various sorts of accommodation within a 30-kilometre radius of the heart of Windsor.

Although it may be a bit of a commute, you should look up the Gateways Inn & Restaurant and the Hampton Terrace Inn. Otherwise, check out the Cranwell Spa and Golf Resort and the Birchwood Inn.

Just 19 kilometres from the main streets is Hancock. This area has 3 accommodation options. Want to know our recommended picks? Start off by checking out the Wyndham Bentley Brook and Jiminy Peak Mountain Resort.

You may also like to try the Federal House Inn, which is 35 kilometres away. Or otherwise you might prefer The Orchards Hotel, just a distance of 25 kilometres from Windsor. Others are the Hampton Inn & Suites Berkshires Lenox, 20 kilometres away, and the Whistler's Inn Bed & Breakfast, 25 kilometres away.

Still haven't got your ideal room? You might just find the thread count you've been looking for in Pittsfield. You'll also be able to have some adventures at the Crane Museum of Papermaking and the Skyline Country Club. The Wagon Wheel Inn and Lenox Inn are a few of the great accommodation options here. 25 kilometres to the northwest of Windsor you can also stay at Williamstown, which is home to the Williamstown Motel and Willows Motel Williamstown. The 62 Center for Theater and Dance and Natural Bridge State Park are up there with the most popular places to check out when visiting Williamstown.

Sitting 25 kilometres southwest of Windsor is Lenox, a regional centre with a population of 2,000. It's where you'll find some sweet attractions, like Tanglewood Music Center, the Berkshire Scenic Railway Museum and Wood's Pond. Got some more time on your hands? See what's happening at the Cranwell Golf Club and Kennedy Park. There are numerous great hotels where you can snap up a room for a night or two in Lenox. We recommend checking out the deals at the Howard Johnson Express Inn - Lenox and Knights Inn Lenox Ma.

After touching down, there's nothing like a bubble bath followed by a kip in a soft comfy bed. So why not snag a room at the Sheraton Hartford Hotel at Bradley Airport or the Holiday Inn Express & Suites Bradley Airport? Each is a stone's throw from Bradley International Airport, which sits 70 kilometres from Windsor's centre.

Windsor hotels essential information

Accommodation
973 hotels
Lowest Price
AU$126
Highest Price
AU$331
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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