Windsor Cottages

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Our top choices for Windsor cottages

Brookside cottage near the mountains and outdoor recreation

Readsboro

Seva L.

includes taxes & fees

7 June - 8 June

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

includes taxes & fees

4 June - 5 June

Berkshires farm, 30+ guests, 50 acres

New Lebanon

includes taxes & fees

15 June - 16 June

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Top Windsor Hotel Reviews

Berkshires Untold

10/10 Excellent

"I loved the funky vibe of this place. It was also very cozy."

Red Roof Inn PLUS+ South Deerfield – Amherst

6/10 Okay

"My husband and I were very disappointed. We decided to stay here for nostalgia's sake because it was the first place we had stayed together 14 years ago. We were saddeProperty is run down. Cobwebs in our room. Highway noise was unbearable. Game room has more machines closed than open. No continental breakfast made it very inconvenient and expensive and wasted so much time. We regret that we booked 2 nights."

Vacation Village in the Berkshires

10/10 Excellent

"While traveling in the area for summer we found Vacation Village. Great jump off point, great amenities, helpful staff, nice set up inside the condo, pots, pans, utensils, glassware, other cooking utensils in good shape. Private decks are a nice touch. Best bargain in the area by far!!! Will be back!"

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

10/10 Excellent

"I spilled an ENTIRE cup of cocoa I was making for my niece. The clerk on was a very kind, friendly young man named Paul. I have worked as a chef for 30 years, the cocoa went EVERYWHERE. He got a mop bucket , I started cleaning my mess up I just know what its like to walk into a mess!! Left by someone else. Paul said "you dont have to finish, ill do it no problem. He was a VERY kind young man. And he was helpful & he cleaned up the rest of the spill. I think your LUCKY to have such kind helpful employees. Just a side note. The hot tub was wayyy hotter then the thermometer( I think). It was unbearable to sit in it for more then a few minutes. And I LOVE being WARM, but everyone around( 3 others came in to use it but could not sit in it for more then a few seconds. Maybe lower it a bit now that winter is GONE!! Also housekeeping was knocking at our door before it was even 11 am!! Were literally just finishing packing up, and shes knocking. I travel extensively. I know check out is 11am. Unless your in vegas snd pay 30$ for a late check out. Beautiful , clean awesome staff(Paul). Clean!! Well be back!"

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