Find hotels in Windsor, MA from ฿2,282
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10 Sep - 11 SepTomorrow
11 Sep - 12 SepThis weekend
11 Sep - 13 SepNext weekend
18 Sep - 20 SepOur top choices for Windsor hotels
1. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Debra
฿3,883
฿4,337 total
includes taxes & fees
13 Sept - 14 Sept
2. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Prasanna
฿3,481
฿3,888 total
includes taxes & fees
13 Sept - 14 Sept
3. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
Basil
฿4,727
฿5,280 total
includes taxes & fees
21 Sept - 22 Sept
4. Hotel On North
Hotel On NorthPittsfield
Drew
฿4,417
฿4,934 total
includes taxes & fees
13 Sept - 14 Sept
5. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
Horace
฿2,043
฿2,282 total
includes taxes & fees
17 Sept - 18 Sept
6. The Revival House
The Revival HouseAdams
James
฿5,449
฿6,087 total
includes taxes & fees
13 Sept - 14 Sept
7. The Yankee Inn
The Yankee InnLenox
Karen
฿3,817
฿4,264 total
includes taxes & fees
22 Sept - 23 Sept
8. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
James
฿4,813
฿5,377 total
includes taxes & fees
13 Sept - 14 Sept
9. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Sarah
฿3,131
฿3,858 total
includes taxes & fees
15 Sept - 16 Sept
10. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
irene
฿2,599
฿2,904 total
includes taxes & fees
13 Sept - 14 Sept
11. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Steve
฿4,015
฿4,484 total
includes taxes & fees
15 Sept - 16 Sept
12. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
Tracy
฿6,573
฿7,342 total
includes taxes & fees
1 Oct - 2 Oct
13. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Nancy
฿4,506
฿5,033 total
includes taxes & fees
30 Sept - 1 Oct
14. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Janis
฿2,902
฿3,411 total
includes taxes & fees
16 Sept - 17 Sept
15. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
฿3,328
฿3,718 total
includes taxes & fees
30 Sept - 1 Oct
16. Harbour House Inn
Harbour House InnCheshire
Gregory
฿8,348
฿8,824 total
includes taxes & fees
21 Sept - 22 Sept
17. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Chris
฿3,407
฿3,806 total
includes taxes & fees
21 Sept - 22 Sept
18. The Springs Motel
The Springs MotelNew Ashford
Elizabeth
฿3,739
฿4,102 total
includes taxes & fees
13 Sept - 14 Sept
19. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Christine
฿4,113
฿4,595 total
includes taxes & fees
14 Sept - 15 Sept
20. Howard Johnson by Wyndham Williamstown
Howard Johnson by Wyndham WilliamstownWilliamstown
Donna
฿3,619
฿4,043 total
includes taxes & fees
14 Sept - 15 Sept
Top Windsor Hotel Reviews
Berkshires Untold
10/10 Excellent
"beautiful place, great staff, would love to go back!"
FairBridge Inn Express
10/10 Excellent
"Room was clean and comfortable."
The Yankee Inn
10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
Willows Motel Williamstown
10/10 Excellent
"Awesome staff plus pet-friendly."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"
Holiday Inn Club Vacations Oak 'n Spruce Resort
8/10 Good
"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."
The Williams Inn
10/10 Excellent
"Exceptional hotel. Friendly vibe."
Jiminy Peak Mountain Resort
10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
Quality Inn Lee - Lenox South
8/10 Good
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
More cheap stays in Windsor
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
฿2,043
฿2,282 total
17 Sept - 18 Sept
includes taxes & fees
5.4/10 (901 reviews)
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
฿3,094
฿3,457 total
14 Sept - 15 Sept
includes taxes & fees
Quality Inn Lee - Lenox South
170 Housatonic Street Lee MA
฿3,328
฿3,718 total
30 Sept - 1 Oct
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
฿3,817
฿4,264 total
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
฿4,015
฿4,484 total
15 Sept - 16 Sept
includes taxes & fees
The Whitlock
16 Church St Lenox MA
฿4,727
฿5,280 total
13 Sept - 14 Sept
includes taxes & fees
8.4/10 Very good! (376 reviews)
