Find hotels in Windsor, MA from 1.808.919 ₫
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28 Aug - 29 AugTomorrow
29 Aug - 30 AugThis weekend
28 Aug - 30 AugNext weekend
4 Sep - 6 SepOur top choices for Windsor hotels
1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Robert
2.466.879 ₫
3.338.086 ₫ total
includes taxes & fees
31 Aug - 1 Sept
2. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
Alex
2.265.762 ₫
2.816.988 ₫ total
includes taxes & fees
31 Aug - 1 Sept
3. The Yankee Inn
The Yankee InnLenox
Karen
3.963.856 ₫
4.427.523 ₫ total
includes taxes & fees
27 Sept - 28 Sept
4. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Myrna
3.077.204 ₫
3.437.341 ₫ total
includes taxes & fees
8 Sept - 9 Sept
5. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
Peter
3.963.856 ₫
4.427.626 ₫ total
includes taxes & fees
20 Sept - 21 Sept
6. Hotel On North
Hotel On NorthPittsfield
Drew
4.667.962 ₫
5.214.114 ₫ total
includes taxes & fees
8 Sept - 9 Sept
7. Blue Vista Motor Lodge
Blue Vista Motor LodgeNorth Adams
5.583.292 ₫
5.901.540 ₫ total
includes taxes & fees
9 Sept - 10 Sept
8. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
Sheila
2.060.162 ₫
2.301.200 ₫ total
includes taxes & fees
31 Aug - 1 Sept
9. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
2.993.494 ₫
3.343.734 ₫ total
includes taxes & fees
21 Sept - 22 Sept
10. Maple Terrace Motel
Maple Terrace MotelWilliamstown
Annette
3.259.750 ₫
3.641.271 ₫ total
includes taxes & fees
15 Sept - 16 Sept
11. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Richard
2.205.318 ₫
2.463.279 ₫ total
includes taxes & fees
30 Aug - 31 Aug
12. Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – AmherstSouth Deerfield
Katie
2.576.506 ₫
2.877.957 ₫ total
includes taxes & fees
7 Sept - 8 Sept
13. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
Rinat
3.324.945 ₫
3.713.962 ₫ total
includes taxes & fees
21 Sept - 22 Sept
14. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
2.859.453 ₫
3.194.009 ₫ total
includes taxes & fees
20 Sept - 21 Sept
15. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
Laura
4.632.757 ₫
5.174.789 ₫ total
includes taxes & fees
3 Sept - 4 Sept
16. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Nancy
3.463.941 ₫
3.869.222 ₫ total
includes taxes & fees
13 Sept - 14 Sept
17. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Janis
2.300.080 ₫
2.703.507 ₫ total
includes taxes & fees
10 Sept - 11 Sept
18. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
ERICIA
1.619.444 ₫
1.808.919 ₫ total
includes taxes & fees
31 Aug - 1 Sept
19. The Central Downtown Inn & Suites
The Central Downtown Inn & SuitesPittsfield
Rena
2.581.722 ₫
2.883.705 ₫ total
includes taxes & fees
3 Sept - 4 Sept
20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Ken
3.077.204 ₫
3.437.341 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Top Windsor Hotel Reviews
Holiday Inn Club Vacations Oak 'n Spruce Resort
10/10 Excellent
"Amazing time. Stayed in the Presidential units. Worth it."
The Red Lion Inn
10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
The Cornell Inn, Lenox & The Berkshires
10/10 Excellent
"Room was"
Berkshires Untold
10/10 Excellent
"Chic bar and outdoor space. Nice remodel."
Quality Inn Lee - Lenox South
10/10 Excellent
"Friendly staff and clean comfortable room! Location is super"
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
10/10 Excellent
"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"
The Black Swan Lee - Lenox, an Ascend Collection Hotel
8/10 Good
"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."
The Yankee Inn
10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Nice place"
More cheap stays in Windsor
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
1.619.444 ₫
1.808.919 ₫ total
31 Aug - 1 Sept
includes taxes & fees
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
2.060.162 ₫
2.301.200 ₫ total
31 Aug - 1 Sept
includes taxes & fees
Red Roof Inn PLUS+ South Deerfield – Amherst
9 Greenfield Rd South Deerfield MA
2.576.506 ₫
2.877.957 ₫ total
7 Sept - 8 Sept
includes taxes & fees
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
2.993.494 ₫
3.343.734 ₫ total
21 Sept - 22 Sept
includes taxes & fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
3.077.204 ₫
3.437.341 ₫ total
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (176 reviews)
The Yankee Inn
461 Pittsfield Rd Lenox MA
3.963.856 ₫
4.427.523 ₫ total
27 Sept - 28 Sept
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Hotels in Windsor with star rating
4 Star Hotels
10 properties
3 Star Hotels
97 properties
2 Star Hotels
51 properties
