Find hotels in Windsor, MA from Rp1.283.218
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Our top choices for Windsor hotels
9.2 out of 10, Wonderful, (125)
Explore Glacial Potholes from this welcoming guesthouse offering snowshoeing, sledding, and snowmobiling on site. Enjoy daily housekeeping and easy access to local attractions like the Shelburne Falls Bowling Alley, with Greenfield Station just a 16-minute drive away.
"Homey spot filled with extra Christmas cheer for the season. Hosts Ellie and Richard are so nice! "
Allison
The price is Rp1.130.625
Rp2.083.658 total
includes taxes & fees
5 Jan - 6 Jan 2026
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – AmherstSouth Deerfield
7.2 out of 10, Good, (1001)
Discover convenience at this South Deerfield hotel, just minutes from Yankee Candle Village and Mount Sugarloaf State Reservation. Enjoy complimentary WiFi and parking, spotless rooms, and attentive 24-hour service, all within 15 minutes of UMass Amherst.
"Helpful and friendly staff, everything I needed was available and at hand, the room was spacious, and the location was perfect for my needs. "
Max
The price is Rp1.492.275
Rp1.666.871 total
includes taxes & fees
29 Dec - 30 Dec
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 IHGSouth Lee
9.0 out of 10, Wonderful, (806)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Centre and Berkshire Theatre Festival.
"Convenient location, very roomy, well equipped kitchen.
"
Carolyn
The price is Rp2.140.650
Rp2.718.569 total
includes taxes & fees
4 Jan - 5 Jan 2026
9.8 out of 10, Exceptional, (196)
This motel offers a peaceful retreat with 2 hot tubs and a rejuvenating sauna. Located near Florida Free Public Library, guests praise the helpful staff and clean rooms. Enjoy free WiFi and parking during your North Adams adventure.
"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "
Jean
The price is Rp2.991.383
Rp3.161.898 total
includes taxes & fees
28 Dec - 29 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1007)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Centre. After working out in the 24-hour fitness centre, savour Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"Room was clean and the staff was super friendly and helpful!"
Ethan
The price is Rp1.680.025
Rp1.876.588 total
includes taxes & fees
12 Jan - 13 Jan 2026
8.8 out of 10, Excellent, (2182)
"Awesome for ski"
Lazar
The price is Rp1.741.531
Rp2.129.038 total
includes taxes & fees
4 Jan - 5 Jan 2026
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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Top Windsor Hotel Reviews
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
10/10 Excellent
Huttopia Berkshires
10/10 Excellent
More cheap stays in Windsor
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
The price is Rp1.267.138 per night from 4 Jan to 5 Jan
Rp1.267.138
Rp1.415.393 total
4 Jan - 5 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
