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Top Windsor Hotel Reviews
Hotel On North
Hotel On NorthPittsfield
10/10 Excellent
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
Steve
The Yankee Inn
The Yankee InnLenox
10/10 Excellent
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
Colleen
Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
10/10 Excellent
It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues.
It was very conveniently located to the activities we were doing on our mini-vacation. There were a couple of issues that developed during our stay, but the staff did an excellent job of dealing with the issues.
Elliott
The Revival House
The Revival HouseAdams
10/10 Excellent
Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7
Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7
Ruby
The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCANorth Adams
10/10 Excellent
Absolutely lovely. Bed was super comfortable, staff was friendly and helpful, lots of places to sit and relax. Easy walk to restaurants and across the street from the MOCA. Nice breakfast and you can even get a drink and a snack in the evening if you want. The sauna, whirlpool and heated pool at the end of October we a pleasant surprise.
Absolutely lovely. Bed was super comfortable, staff was friendly and helpful, lots of places to sit and relax. Easy walk to restaurants and across the street from the MOCA. Nice breakfast and you can even get a drink and a snack in the evening if you want. The sauna, whirlpool and heated pool at the end of October we a pleasant surprise.
Stacey
Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
10/10 Excellent
Clean , comfortable place to stay after skiing all day.
Clean , comfortable place to stay after skiing all day.
Anonymous traveler
Harbour House Inn
Harbour House InnCheshire
10/10 Excellent
The Harbor House Inn is a wonderfully situated B and B, located 8 miles south of North Adams. The welcome is warm, and amenities are generous. Highly recommended.
The Harbor House Inn is a wonderfully situated B and B, located 8 miles south of North Adams. The welcome is warm, and amenities are generous. Highly recommended.
Anonymous traveler
Maple Terrace Motel
Maple Terrace MotelWilliamstown
10/10 Excellent
Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates.
Arrived late after office closed. Easy arrangements for check in made with no issues. Light in room was on to welcome me. Room was very clean with nice appointments of water, coffee, tea, chocolates.
Eric
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
10/10 Excellent
Solid
Solid
Colton
Berkshires Untold
Berkshires UntoldLenox
10/10 Excellent
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
Jill
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
10/10 Excellent
The staff could not have been more helpful, great location and the facility extremely clean. We were shocked about how amazing this place was
The staff could not have been more helpful, great location and the facility extremely clean. We were shocked about how amazing this place was
t
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
10/10 Excellent
Room was so nice. Bed was comfortable. Overall glad we stayed here.
Room was so nice. Bed was comfortable. Overall glad we stayed here.
Alyssa
Willows Motel Williamstown
Willows Motel WilliamstownWilliamstown
10/10 Excellent
This motel is in a convenient location for visiting Williams College. Rooms are clean and the mattresses are very comfortable. They have the largest TV screens I've seen in any motel. Their Continental breakfast is extensive with a variety of pastries, breads, and beverages. The staff is kind, caring, helpful, and accommodating.
This motel is in a convenient location for visiting Williams College. Rooms are clean and the mattresses are very comfortable. They have the largest TV screens I've seen in any motel. Their Continental breakfast is extensive with a variety of pastries, breads, and beverages. The staff is kind, caring, helpful, and accommodating.
Sandra
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art HotelAdams
10/10 Excellent
The house was very unique. Everything was perfect.
The room was the nicest I've stayed in!!!
The house was very unique. Everything was perfect.
The room was the nicest I've stayed in!!!
Esther
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
10/10 Excellent
Great place!
Great place!
Ann
Williamstown Motel
Williamstown MotelWilliamstown
10/10 Excellent
Yes no frills but good for an economic stay.
Great coffee at The Coffee Shop Williamstown nearby
Yes no frills but good for an economic stay.
Great coffee at The Coffee Shop Williamstown nearby
Grantley
Element by Marriott Lenox Berkshires
Element by Marriott Lenox BerkshiresLenox
10/10 Excellent
Clean and spacious room.
Clean and spacious room.
Richard
Frequently Asked Questions
What is the best area to stay in Windsor?
The best area to stay in Windsor, Massachusetts, is near the town center, particularly along Route 9, for convenient access to local attractions and the Berkshire Mountains.
Windsor itself is a small, quiet town known for its natural beauty and outdoor activities. Staying near the town center provides easy access to the Windsor Historical Society and the local general store. This area is ideal for travelers seeking a peaceful retreat and proximity to hiking trails and scenic drives.
For couples looking for a tranquil getaway with access to nature, staying in a guesthouse or inn located in the hills surrounding the town center is an excellent choice. These accommodations often offer picturesque views and a chance to relax away from any hustle, while still being a short drive from attractions like the Windsor State Forest.
When is the best time to go to Windsor?
The best time to visit Windsor is during the summer months, from June to August, when the weather is warm and conducive to outdoor activities, or in the fall, from September to October, for stunning foliage.
Summer in Windsor offers pleasant temperatures, typically ranging from the mid-60s to high 70s Fahrenheit, making it ideal for exploring the natural beauty of the Berkshires. This season is great for hiking trails, enjoying the numerous lakes and ponds, and participating in local outdoor events. The longer daylight hours also allow for more extensive sightseeing.
For those who appreciate natural beauty, early to mid-fall is a spectacular time to visit. The Berkshire region is renowned for its vibrant autumn colors, with the hillsides transforming into a canvas of reds, oranges, and yellows.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Windsor.
How much is the nightly rate at a Windsor hotel?
Prices for hotels in Windsor often vary, but you can find a great deal from $72 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.