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Cheap Windsor Hotels
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$170 nightly
The price is $189 total per night
$189 total
Jul 12 - Jul 13
Total with taxes and fees
13.55 mi from city center
With a stay at Hotel Downstreet, an Ascend Collection Hotel, you'll be centrally located in North Adams, within a 15-minute drive of Green Mountain National Forest and Western Gateway Heritage State Park.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night
$173 total
Jun 21 - Jun 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
12.95 mi from city center
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 Marketplace.
Pool
Hot Tub
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$136 nightly
The price is $152 total per night
$152 total
Jun 21 - Jun 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.04 mi from city center
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 Coaster.
The Yankee Inn
461 Pittsfield Rd Lenox MA
$127 nightly
The price is $142 total per night
$142 total
Jun 21 - Jun 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.45 mi from city center
Located in Lenox, The Yankee Inn is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.
Berkshires Untold
194 Pittsfield Rd Lenox MA
$151 nightly
The price is $169 total per night
$169 total
Jun 23 - Jun 24
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.37 mi from city center
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
The Red Lion Inn
30 Main Street Stockbridge MA
$191 nightly
The price is $214 total per night
$214 total
Jul 1 - Jul 2
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.72 mi from city center
When you stay at The Red Lion Inn in Stockbridge, you'll be next to a golf course, within a 15-minute drive of National Shrine of the Divine Mercy and Tanglewood Music Center.
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
$99 nightly
The price is $110 total per night
$110 total
Jul 1 - Jul 2
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
22.04 mi from city center
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 Yankee Candle Village.
Hotel On North
297 North Street Pittsfield MA
$229 nightly
The price is $256 total per night
$256 total
Jun 21 - Jun 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.24 mi from city center
Located in Pittsfield, Hotel On North is a 1-minute drive from Barrington Stage Company and 7 minutes from Bousquet Ski Area.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
$131 nightly
The price is $147 total per night
$147 total
Jun 21 - Jun 22
Total with taxes and fees
19.96 mi from city center
When you 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 National Shrine of the Divine Mercy and Tanglewood Music Center.
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
$140 nightly
The price is $156 total per night
$156 total
Jun 22 - Jun 23
Total with taxes and fees
Free Cancellation
13.11 mi from city center
With a stay at Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG in Pittsfield, you'll be within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
$150 nightly
The price is $168 total per night
$168 total
Jun 25 - Jun 26
Total with taxes and fees
16.94 mi from city center
When you stay at The Black Swan Lee - Lenox, an Ascend Collection Hotel in Lee, you'll be on the waterfront, within a 15-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
$127 nightly
The price is $142 total per night
$142 total
Jun 22 - Jun 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.51 mi from city center
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.
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.
Windsor hotels essential information
Accommodation | 964 hotels |
|---|---|
Lowest Price | $110 |
Highest Price | $256 |
Popular hotels | Hotel Downstreet, an Ascend Collection Hotel, Berkshire Mountain Lodge, Vacation Village in the Berkshires, The Yankee Inn, Berkshires Untold, The Red Lion Inn, Red Roof Inn PLUS+ South Deerfield – Amherst, Hotel On North, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Hampton Inn & Suites Berkshires-Lenox |
Most Recent Windsor Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
5 out of 5
Posted 11 hours ago
CheapTickets Verified Review
"Had a wonderful stay. Staff is friendly and helpful. Breakfast was great, especially the automatic pancake maker. Had a wonderful dinner from Mint restaurant. The room was very clean and had the most comfortable hotel bed ever. The shower was a gleaming white as if it had never been used. The swan soap dish was a lovely touch. The view of the lake and mountains is spectacular. Would definitely stay here again."
A verified traveler stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel
