Book Windsor hotels

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Check hotel availability in Windsor

Cheap Windsor hotels

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AU$166 per night from 24 May to 25 May
AU$166
24 May - 25 May
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is AU$154 per night from 25 May to 26 May
AU$154
25 May - 26 May
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
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$148 per night from 14 May to 15 May
AU$148
14 May - 15 May
includes taxes & fees
Located in Williamstown, Vacation Village in the Berkshires is a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Opens in a new windowVacation Village in the Berkshires
Save an average of 15% on thousands of hotels when you're signed in
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
The price is AU$222 per night from 2 June to 3 June
AU$222
2 June - 3 June
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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is AU$303 per night from 18 May to 19 May
AU$303
18 May - 19 May
includes taxes & fees
With a stay at The Red Lion Inn in Stockbridge, you'll be next to a golf course, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Opens in a new windowThe Red Lion Inn
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$160 per night from 31 May to 1 June
AU$160
31 May - 1 June
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
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 25 May to 26 May
AU$184
25 May - 26 May
includes taxes & fees
Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.
Opens in a new windowHampton Inn & Suites Berkshires-Lenox
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
The price is AU$224 per night from 18 May to 19 May
AU$224
18 May - 19 May
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 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
The price is AU$187 per night from 27 May to 28 May
AU$187
27 May - 28 May
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
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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
998 hotels
Lowest Price
AU$148
Highest Price
AU$303
Popular hotels
Berkshire Mountain Lodge, Berkshires Untold, Vacation Village in the Berkshires, Hotel Downstreet, an Ascend Collection Hotel, The Red Lion Inn, Red Roof Inn PLUS+ South Deerfield – Amherst, Hampton Inn & Suites Berkshires-Lenox, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel

Most recent Windsor hotel reviews

Top Picks

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.