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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$180 per night from 18 Mar to 19 Mar
AU$180
18 Mar - 19 Mar
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is AU$187 per night from 5 Apr to 6 Apr
AU$187
5 Apr - 6 Apr
includes taxes & fees
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 16 Apr to 17 Apr
AU$179
16 Apr - 17 Apr
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
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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$110 per night from 1 Apr to 2 Apr
AU$110
1 Apr - 2 Apr
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
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$315 per night from 19 Mar to 20 Mar
AU$315
19 Mar - 20 Mar
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 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 refundable
The price is AU$206 per night from 22 Mar to 23 Mar
AU$206
22 Mar - 23 Mar
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
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$140 per night from 23 Mar to 24 Mar
AU$140
23 Mar - 24 Mar
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
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$183 per night from 20 Mar to 21 Mar
AU$183
20 Mar - 21 Mar
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
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
Fully refundable
The price is AU$145 per night from 7 Apr to 8 Apr
AU$145
7 Apr - 8 Apr
includes taxes & fees
With a stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center ...
Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
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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
1,000 hotels
Lowest Price
AU$110
Highest Price
AU$315
Popular hotels
Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, Berkshire Mountain Lodge, Berkshires Untold, The Williams Inn, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel

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