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Hotels in Windsor

Choose from 959 Windsor Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 6 min drive from Tanglewood Music Center
The price is $115 per night from May 1 to May 2
$115
includes taxes & fees
May 1 - May 2
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (570 reviews)
"Loved the entire vibe of the property. Decor, ease of check in / out."

Reviewed on Apr 27, 2025

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
  • 13 min drive from Tanglewood Music Center
The price is $134 per night from May 14 to May 15
$134
includes taxes & fees
May 14 - May 15
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (625 reviews)
"We loved our stay here. The location is beautiful and close to great hiking spots and nice towns . The resort amenities are awesome. The staff was friendly. We’d love to come back"

Reviewed on Apr 26, 2025

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
  • 8 min drive from Tanglewood Music Center
The price is $120 per night from May 4 to May 5
$120
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,000 reviews)
"It is convenient"

Reviewed on Apr 29, 2025

The Yankee, Trademark Collection by Wyndham
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
  • 5 min drive from Tanglewood Music Center
The price is $122 per night from May 1 to May 2
$122
includes taxes & fees
May 1 - May 2
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
9/10 Wonderful! (1,006 reviews)
"Friendly staff, great location for hiking and biking in the Berkshires."

Reviewed on Apr 27, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
  • 58 min drive from Tanglewood Music Center
The price is $141 per night from May 1 to May 2
$141
includes taxes & fees
May 1 - May 2
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (999 reviews)
"Very nice and funky place! Clean, friendly nice staff. Have already stayed here twice and plan to stay again!❤️"

Reviewed on Apr 18, 2025

Hotel Downstreet, Ascend Hotel Collection
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
  • 1 hour drive from Tanglewood Music Center
The price is $334 per night from May 1 to May 2
$334
includes taxes & fees
May 1 - May 2
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (447 reviews)
"Wonderful staff! Welcoming, relaxed, great personalities."

Reviewed on Apr 28, 2025

The Williams Inn
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
  • 12 min drive from Tanglewood Music Center
The price is $211 per night from May 4 to May 5
$211
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,003 reviews)
"we stayed in the Stevens house. The driveway could use some attention."

Reviewed on Apr 30, 2025

The Red Lion Inn
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
  • 5 min walk from Tanglewood Music Center
The price is $85 per night from May 1 to May 2
$85
includes taxes & fees
May 1 - May 2
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (387 reviews)
"Receptionist was excellent. The room had the smell of an old building so we opened the windows to air it out and then it was fine. A night stand was damaged so we informed the receptionist but overall we were comfortable."

Reviewed on Apr 27, 2025

The Constance, The Whitlock, & The Dewey By The Lenox Collection
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 35 min drive from Tanglewood Music Center
The price is $130 per night from May 18 to May 19
$130
includes taxes & fees
May 18 - May 19
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,798 reviews)
"Great property"

Reviewed on Apr 27, 2025

Vacation Village in the Berkshires
Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
  • 17 min drive from Tanglewood Music Center
The price is $136 per night from May 12 to May 13
$136
includes taxes & fees
May 12 - May 13
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (710 reviews)
"na"

Reviewed on Apr 25, 2025

Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
  • 16 min drive from Tanglewood Music Center
The price is $111 per night from May 28 to May 29
$111
includes taxes & fees
May 28 - May 29
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (776 reviews)
"Friendly staff"

Reviewed on Apr 27, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
  • 8 min drive from Tanglewood Music Center
The price is $77 per night from May 1 to May 2
$77
includes taxes & fees
May 1 - May 2
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.4/10 Good! (718 reviews)
"Comfortable"

Reviewed on Apr 27, 2025

Howard Johnson by Wyndham Lenox
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.

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