The Best Windsor, MA Chalets from $70

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Our top choices for Windsor chalets

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Charlemont

Georgia P.

$1,209 nightly

Jul 26 - Jul 27

Total with taxes and fees

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Top Windsor Hotel Reviews

The Yankee Inn

8/10 Good

"The Inn is a bit older but well maintained. The outdoor and indoor pools were lovely. The bed was comfortable with adequate bedding. Our bathtub was quite outdated but the rest was updated and fine. I would stay again - Good value and excellent location to Lenox and attractions."

Berkshire Mountain Lodge

10/10 Excellent

"We enjoyed our stay at this hotel very much. We were only there 2 nights and wished we were staying longer. No view from our room but the area is beautiful and there is much to do. Our 1-bedroom room was spacious and well-equipped. The only problem was the very low toilet and they are replacing those gradually. We could have used more info at check-in as to the indoor pool and what else is available at the hotel. Check out went well and employee was very helpful and friendly."

FairBridge Inn Express

8/10 Good

"Room was clean and in excellent condition - apparently they have totally renovated since earlier reviews that mentioned severe problems. The exterior could use some paint, but the room was perfectly clean and fairly spacious. All the little things, like good A/C, shower temp/pressure, a working mini-fridge, etc., were completely fine. Complaints: I couldn't get the WiFi to work. Also: it's not in the most scenic part of Pittsfield, but it's just minutes from the nicer areas, and a short walk to fast food or decent chain restaurants like Friendlys, Applebees, and Starbucks."

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Windsor Chalets information

Number of reviews	12,405
Accommodation	4 Chalets
Lowest Price	$70
Highest Price	$246

Room 1

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Our top choices for Windsor chalets

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

The Yankee Inn

Quality Inn Lee - Lenox South

Berkshire Mountain Lodge

Berkshires Untold

Vacation Village in the Berkshires

Best Western Plus Berkshire Hills Inn & Suites

The Cornell Inn, Lenox & The Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

FairBridge Inn Express

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Windsor Chalets information

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