Explore top 2026 4 Star Hotels in Windsor
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Top Windsor 4 Star hotels
The Williams Inn
"Wonderful Inn with wonderful people in a wonderful town. One of my favorite places anywhere."
Reviewed on May 30, 2026
The Central Downtown Inn & Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Devonfield Inn B&B
"Excellent food and helpful staff"
Reviewed on May 13, 2026
Seven Hills Inn
The Inn at Stockbridge
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
Reviewed on Nov 24, 2025
Lakehouse Inn
"Clean rooms and staff were very knowledgeable about the area. Breakfast was very good. Beautiful room and view on second floor. Would recommend as a place to get away from it all!!"
Reviewed on Jun 5, 2026
33 Main
"Every point of contact I had at 33 Main was friendly, efficient, and accommodating. It’s evident Donna and her team run the inn with love. It’s clean and gorgeously furnished on the inside. You’ll recognize it from the outside, because it’s the most charmingly decorated on the block. I stayed in ..."
Reviewed on Oct 24, 2025
Hampton Terrace Inn
"Hot tub in the cottage was wonderful. The provided guide was very comprehensive and we appreciated all the amenities available in the main and carriage house."
Reviewed on Mar 3, 2026
Family-friendly Hancock Home: Walk to Slopes!
4 Star Hotels Windsor
Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?
Come on, you deserve it!
The best part about staying in Windsor 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.
Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.
The best four star hotels in Windsor will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!
If you’re looking for 4 star hotels in Windsor, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.
Recent Windsor hotel reviews by fellow wanderers
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
"Room was very clean and staff went far a beyond to accommodate my husbands needs."
