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Cheap Windsor Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
$110 nightly
The price is $123 total per night
$123 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Pool
Parking included
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$115 nightly
The price is $128 total per night
$128 total
Nov 4 - Nov 5
Total with taxes and fees
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
The Yankee Inn
461 Pittsfield Rd Lenox MA
$106 nightly
The price is $118 total per night
$118 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Pool
Hot Tub
Holiday Inn Club Vacations Oak 'n Spruce Resort
190 Meadow Street South Lee MA
$129 nightly
The price is $144 total per night
$144 total
Oct 8 - Oct 9
Total with taxes and fees
19.86 mi from city center
With a stay at Holiday Inn Club Vacations Oak 'n Spruce Resort in South Lee, you'll be near ski lifts, within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Pool
Air conditioning
Berkshires Untold
194 Pittsfield Rd Lenox MA
$136 nightly
The price is $152 total per night
$152 total
Nov 1 - Nov 2
Total with taxes and fees
14.37 mi from city center
Located in Lenox, Berkshires Untold is within a 10-minute drive of Shakespeare and Company and The Mount.
Pet friendly
Parking included
The Red Lion Inn
30 Main Street Stockbridge MA
$223 nightly
The price is $250 total per night
$250 total
Nov 3 - Nov 4
Total with taxes and fees
20.72 mi from city center
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.
Pool
Spa
Hotel On North
297 North Street Pittsfield MA
$127 nightly
The price is $141 total per night
$141 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Pet friendly
Parking included
The Williams Inn
101 Spring Street Williamstown MA
$212 nightly
The price is $236 total per night
$236 total
Nov 1 - Nov 2
Total with taxes and fees
16.04 mi from city center
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Pet friendly
Parking included
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
$103 nightly
The price is $115 total per night
$115 total
Nov 4 - Nov 5
Total with taxes and fees
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.
Pool
Hot Tub
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
$119 nightly
The price is $133 total per night
$133 total
Nov 1 - Nov 2
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.
Pool
Hot Tub
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
$116 nightly
The price is $129 total per night
$129 total
Nov 1 - Nov 2
Total with taxes and fees
16.94 mi from city center
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 and Berkshire Mountain Country Store.
Breakfast included
Pet friendly
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
$89 nightly
The price is $100 total per night
$100 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Pet friendly
Parking included
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 | 978 hotels |
|---|---|
Lowest Price | $100 |
Highest Price | $250 |
Popular hotels | Vacation Village in the Berkshires, Berkshire Mountain Lodge, The Yankee Inn, Holiday Inn Club Vacations Oak 'n Spruce Resort, Berkshires Untold, The Red Lion Inn, Hotel On North, The Williams Inn, Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG, Hotel Downstreet, an Ascend Collection Hotel, The Black Swan Lee - Lenox, an Ascend Collection Hotel, Red Roof Inn PLUS+ South Deerfield – Amherst |
Most Recent Windsor Hotel Reviews
Vacation Village in the Berkshires
5 out of 5
Posted 8 hours ago
CheapTickets Verified Review
"Love the fireplace in our room! The amenities always make this place worth the money, and the views to top it all off!!"
A verified traveler stayed at Vacation Village in the Berkshires
