Windsor hotels from RM283
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12 Aug - 13 AugTomorrow
13 Aug - 14 AugThis weekend
14 Aug - 16 AugNext weekend
21 Aug - 23 AugOur top choices for Windsor hotels
1. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
Jermaine
RM466
RM520 total
includes taxes & fees
3 Sept - 4 Sept
2. The Yankee Inn
The Yankee InnLenox
Karen
RM674
RM753 total
includes taxes & fees
13 Sept - 14 Sept
3. The Revival House
The Revival HouseAdams
James
RM678
RM757 total
includes taxes & fees
16 Aug - 17 Aug
4. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
Victoria
RM573
RM640 total
includes taxes & fees
2 Sept - 3 Sept
5. FairBridge Inn Express
FairBridge Inn ExpressPittsfield
DAVID
RM254
RM283 total
includes taxes & fees
17 Aug - 18 Aug
6. Harbour House Inn
Harbour House InnCheshire
Gregory
RM1,038
RM1,097 total
includes taxes & fees
17 Aug - 18 Aug
7. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
Myrna
RM486
RM543 total
includes taxes & fees
13 Sept - 14 Sept
8. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
Nancy
RM563
RM629 total
includes taxes & fees
13 Sept - 14 Sept
9. The Trail in Adams - Berkshiresโ Art Hotel
The Trail in Adams - Berkshiresโ Art HotelAdams
Jenna
RM880
RM983 total
includes taxes & fees
8 Sept - 9 Sept
10. Blue Vista Motor Lodge
Blue Vista Motor LodgeNorth Adams
Frederic
RM1,006
RM1,064 total
includes taxes & fees
18 Aug - 19 Aug
11. The Springs Motel
The Springs MotelNew Ashford
Shakeila
RM592
RM650 total
includes taxes & fees
13 Sept - 14 Sept
12. Berkshire Inn
Berkshire InnPittsfield
christopher
RM368
RM411 total
includes taxes & fees
19 Aug - 20 Aug
13. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
Ken
RM535
RM598 total
includes taxes & fees
7 Sept - 8 Sept
14. Hotel On North
Hotel On NorthPittsfield
Dragana
RM731
RM817 total
includes taxes & fees
7 Sept - 8 Sept
15. Rodeway Inn
Rodeway InnAdams
Andrew
RM294
RM329 total
includes taxes & fees
25 Aug - 26 Aug
16. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
Christine
RM438
RM490 total
includes taxes & fees
31 Aug - 1 Sept
17. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
Luciane
RM323
RM361 total
includes taxes & fees
7 Sept - 8 Sept
18. Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
Richard
RM423
RM473 total
includes taxes & fees
27 Aug - 28 Aug
19. Cozy Corner Motel
Cozy Corner MotelWilliamstown
Jeremy
RM360
RM424 total
includes taxes & fees
9 Sept - 10 Sept
20. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
Karilyn
RM387
RM524 total
includes taxes & fees
31 Aug - 1 Sept
Top Windsor Hotel Reviews
The Whitlock
10/10 Excellent
"We visited on a Tanglewood concert night in August. Check-in process was super easy and staff was reachable almost immediately via text. Very clean, updated and well-appointed room. Bar area was quiet but someone was always accessible to get us ice or an adult beverage. Complimentary water & coffee. Lovely outdoor courtyard where we enjoyed the fire pit post-concert. Great locationโฆ walkable to all shops and restaurants! Would highly recommend and will definitely stay here again!"
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"Loved our two-day stay at the Black Swan Inn. We were in the area because we were taking a few programs at the Kripalu Center for one of the days. The room itself was clean, the hall areas could do with better maintenance (which is why I gave that 4 stars) The staff was helpful with any questions. Continental breakfast was decent (though they could do with better coffee). We wished we could have enjoyed the Indian restaurant "Mint" next door, which I hear is really good, but they were closed on Tuesdays, so it was a matter of timing..., but we hope to have a chance next time we are in the area. One of my favorite parts of the property is that it sits by a clean lovely lake, and there are seating areas to enjoy the view anytime of day just to unwind. They also have kayak rentals for those who enjoy the activity. Another wonderful treat- it is near High Lawn Farm, only a 3-min drive from the Inn. It is beautiful there, and cute Jersey cows roam freely, when they are ready they go on their own time into a building where they lay on heated water beds while being milked (I kid you not!). Their dairy products and ice-cream are excellent, worth taking the short drive there. The town center of Lee has some nice restaurants and boutiques within a 5-8 min drive. It was a memorable stay and hope to be back there again soon."
Berkshire Mountain Lodge
10/10 Excellent
"I did not expect the faciity to be what it was, a resort. It was just awesome and everything was perfect. The only thing was, if I knew a little more about the place, I would have brought some items I wouldn't if I was in a hotel. This place has so much to offer in some catagories."
Berkshires Untold
8/10 Good
"Lovely man at check in for our overnight ( to see Hugh Jackman at 7 pm at Tanglewood lucky us!๐ Checked that food would be available in their bar upon our trying as has driven 2+ hrs assured yes until just before 10 pm closing. Called once on way back at 9:10 for 10 min drive to dbl check as hungry. Woman said no, they stopping serving at 9... luckily she rec one place nearby which was still open for food til midnight! Wow in Lenox! Very packed loud and fun w locals & Jackman fans..got wines, friendly bartenders, ordered yummy plates of tacos , sandwich and ended eve on a great note . Go to OMBRA if hungry after 9! Small complaint this am also.. we ordered a bagel & a berry salad from the hotel's brkfst menu to go as needed to drive back home mid am.. Opened it and about 1/2 cup of mixed berries ..for $11.00... Think the bagel was 8. Oh well -worth the splurge to see Hugh ๐and only 10 min drive to Tanglewood & downtown Lenox! Hotel not walkable to anything but ez parking & very cute interior & bar & seating areas!"
The Yankee Inn
10/10 Excellent
"Very nice and convenient hotel."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Nice!"
The Williams Inn
10/10 Excellent
"The dinner we had was very good, excellent bar, great wait staff. On the whole it was very satisfying. "
The Cornell Inn, Lenox & The Berkshires
10/10 Excellent
"The staff were terrific from welcome to departure. Breakfast was diverse and tasty. The Inn location was great for Tanglewood and local restaurants. We intend to return should we be in that area again!"
Jiminy Peak Mountain Resort
10/10 Excellent
"Quiet and serene. Great weekend escape!"
More cheap stays in Windsor
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
RM254
RM283 total
17 Aug - 18 Aug
includes taxes & fees
5.4/10 (870 reviews)
Howard Johnson by Wyndham Lenox
462 Pittsfield Rd Lenox MA
RM323
RM361 total
7 Sept - 8 Sept
includes taxes & fees
Red Roof Inn PLUS+ South Deerfield โ Amherst
9 Greenfield Rd South Deerfield MA
RM404
RM451 total
19 Aug - 20 Aug
includes taxes & fees
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
RM466
RM520 total
3 Sept - 4 Sept
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
RM535
RM598 total
7 Sept - 8 Sept
includes taxes & fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
RM674
RM753 total
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (1,024 reviews)
