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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
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 27 Aug to 28 Aug
AU$203
27 Aug - 28 Aug
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 ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
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 ...
Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 31 Aug to 1 Sept
AU$122
31 Aug - 1 Sept
includes taxes & fees
Located in Pittsfield, FairBridge Inn Express is in the suburbs, a 4-minute drive from Crane Museum of Papermaking and 6 minutes from Berkshire Athenaeum.
FairBridge Inn Express
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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$393 per night from 15 Sept to 16 Sept
AU$393
15 Sept - 16 Sept
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.
The Williams 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$275 per night from 17 Aug to 18 Aug
AU$275
17 Aug - 18 Aug
includes taxes & fees
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Berkshires Untold
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 14 Sept to 15 Sept
AU$247
14 Sept - 15 Sept
includes taxes & fees
A stay at Hotel Downstreet, Ascend Hotel Collection places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Hotel Downstreet, Ascend Hotel Collection
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$179 per night from 2 Sept to 3 Sept
AU$179
2 Sept - 3 Sept
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 ...
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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$396 per night from 17 Aug to 18 Aug
AU$396
17 Aug - 18 Aug
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 ...
The Red Lion Inn
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$230 per night from 16 Sept to 17 Sept
AU$230
16 Sept - 17 Sept
includes taxes & fees
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
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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
980 hotels
Lowest Price
AU$122
Highest Price
AU$396
Popular hotels
Vacation Village in the Berkshires, Berkshire Mountain Lodge, FairBridge Inn Express, The Williams Inn, Berkshires Untold, Hotel Downstreet, Ascend Hotel Collection, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham

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