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Cheap Windsor hotels

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 AU$226 per night from 30 Apr to 1 May
AU$226
includes taxes & fees
30 Apr - 1 May
With a stay at Berkshires Untold in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
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$209 per night from 28 Apr to 29 Apr
AU$209
includes taxes & fees
28 Apr - 29 Apr
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 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$170 per night from 24 Apr to 25 Apr
AU$170
includes taxes & fees
24 Apr - 25 Apr
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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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$372 per night from 20 Apr to 21 Apr
AU$372
includes taxes & fees
20 Apr - 21 Apr
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
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$221 per night from 30 Apr to 1 May
AU$221
includes taxes & fees
30 Apr - 1 May
With a stay at Hotel Downstreet, Ascend Hotel Collection, you'll be centrally located in North Adams, within a 10-minute drive of Williams College and Western ...
Hotel Downstreet, 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 AU$302 per night from 12 May to 13 May
AU$302
includes taxes & fees
12 May - 13 May
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 Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 28 Apr to 29 Apr
AU$162
includes taxes & fees
28 Apr - 29 Apr
With a stay at The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection

The Constance, The Whitlock, & The Dewey By The Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
The price is AU$142 per night from 4 May to 5 May
AU$142
includes taxes & fees
4 May - 5 May
With a stay at The Constance, The Whitlock, & The Dewey By The Lenox Collection in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and Lenox ...
The Constance, The Whitlock, & The Dewey By The Lenox Collection
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 20 Apr to 21 Apr
AU$191
includes taxes & fees
20 Apr - 21 Apr
With a stay at Hotel On North in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.
Hotel On North
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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
939 hotels
Lowest Price
AU$142
Highest Price
AU$372
Popular hotels
Life House Berkshires, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Yankee, Trademark Collection by Wyndham, The Williams Inn, Hotel Downstreet, Ascend Hotel Collection, The Red Lion Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection, The Constance, The Whitlock, & The Dewey By The Lenox Collection, Hotel On North

Most recent Windsor hotel reviews

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