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Hotels in Windsor

Choose from 937 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 $108 per night from Apr 17 to Apr 18
$108
includes taxes & fees
Apr 17 - Apr 18
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! (540 reviews)
"A motel style well thought out hotel, tastefully designed,very comfortable room with fabulous beds. Have no hesitation in recommending it."

Reviewed on Apr 2, 2025

Life House Berkshires
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 $99 per night from Apr 13 to Apr 14
$99
includes taxes & fees
Apr 13 - Apr 14
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! (1,001 reviews)
"Love them"

Reviewed on Apr 1, 2025

The Yankee, Trademark Collection by Wyndham
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 $147 per night from Apr 6 to Apr 7
$147
includes taxes & fees
Apr 6 - Apr 7
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 ...
8.8/10 Excellent! (615 reviews)
"Clean and great location"

Reviewed on Mar 28, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 $249 per night from Apr 6 to Apr 7
$249
includes taxes & fees
Apr 6 - Apr 7
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! (434 reviews)
"조용하고 깨끗한 룸이 마음에 들었지만 힛팅 소리가 크게들려 중간에 잠이 깼다"

Reviewed on Apr 1, 2025

The Williams Inn
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 $146 per night from Apr 16 to Apr 17
$146
includes taxes & fees
Apr 16 - Apr 17
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! (1,792 reviews)
"The location to jimney peak was great."

Reviewed on Mar 26, 2025

Vacation Village in the Berkshires
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 Apr 6 to Apr 7
$141
includes taxes & fees
Apr 6 - Apr 7
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! (1,001 reviews)
"Great value."

Reviewed on Mar 29, 2025

Hotel Downstreet, Ascend Hotel Collection
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 $103 per night from Apr 10 to Apr 11
$103
includes taxes & fees
Apr 10 - Apr 11
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! (1,001 reviews)
"Excellent"

Reviewed on Mar 29, 2025

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 $178 per night from Apr 14 to Apr 15
$178
includes taxes & fees
Apr 14 - Apr 15
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! (1,000 reviews)
"Historic property with a bunch to do. Pool was great!"

Reviewed on Mar 31, 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 $91 per night from May 4 to May 5
$91
includes taxes & fees
May 4 - May 5
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. ...
8.4/10 Very Good! (381 reviews)
"This inn is located in a very convenient location to the town center where there are numerous boutique shops. The inn itself is quiet, clean, and safe, with a small 24-hour open dining room with a coffee station that offers Green Mountain coffee pods, and pop-corn and cracker snacks. The stay includes ..."

Reviewed on Mar 25, 2025

The Constance, The Whitlock, & The Dewey By The Lenox Collection
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 $135 per night from Apr 6 to Apr 7
$135
includes taxes & fees
Apr 6 - Apr 7
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! (697 reviews)
"Staff was very helpful and kind"

Reviewed on Mar 28, 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 $116 per night from Apr 11 to Apr 12
$116
includes taxes & fees
Apr 11 - Apr 12
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! (763 reviews)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area."

Reviewed on Mar 18, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
  • 10 min drive from Tanglewood Music Center
The price is $144 per night from Apr 4 to Apr 5
$144
includes taxes & fees
Apr 4 - Apr 5
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (447 reviews)
"We really enjoyed our stay. Rooms were spacious,bed was comfy, kitchen was great and grocery store across the street and Guidos gourmet grocery store just down the street. Loved the pool and hot tub! Would stay again!"

Reviewed on Mar 29, 2025

Berkshire Mountain Lodge
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.

Find cheap hotels in Windsor

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