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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$172 per night from 12 Nov to 13 Nov
AU$172
12 Nov - 13 Nov
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
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 ...
Opens in a new windowBerkshire Mountain Lodge
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$175 per night from 11 Nov to 12 Nov
AU$175
11 Nov - 12 Nov
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 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$334 per night from 17 Nov to 18 Nov
AU$334
17 Nov - 18 Nov
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
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$158 per night from 2 Nov to 3 Nov
AU$158
2 Nov - 3 Nov
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
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$145 per night from 23 Nov to 24 Nov
AU$145
23 Nov - 24 Nov
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$271 per night from 9 Nov to 10 Nov
AU$271
9 Nov - 10 Nov
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
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 refundableReserve now, pay when you stay
The price is AU$181 per night from 4 Nov to 5 Nov
AU$181
4 Nov - 5 Nov
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
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
The price is AU$322 per night from 4 Nov to 5 Nov
AU$322
4 Nov - 5 Nov
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
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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
989 hotels
Lowest Price
AU$145
Highest Price
AU$334
Popular hotels
Vacation Village in the Berkshires, Berkshire Mountain Lodge, Holiday Inn & Suites Pittsfield-Berkshires by IHG, The Williams Inn, Berkshires Untold, Red Roof Inn PLUS+ South Deerfield – Amherst, Hotel Downstreet, an Ascend Collection Hotel, The Black Swan Lee - Lenox, an Ascend Collection Hotel, The Red Lion Inn

Most recent Windsor hotel reviews

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