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Our top choices for Windsor 3-star hotels




1. Vacation Village in the Berkshires
Vacation Village in the Berkshires3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,839 reviews)
8.8/10
Excellent
(2,839 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
"Gorgeous setting, comfortable beds and luxurious accommodations."Carol




2. Berkshire Mountain Lodge
Berkshire Mountain Lodge3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,266 reviews)
9.0/10
Wonderful
(1,266 reviews)
"Excellent stay!!!!"
"Excellent stay!!!!"Susan J




3. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,005 reviews)
9.2/10
Wonderful
(1,005 reviews)
"Nice place to stay"
"Nice place to stay"Michael




4. Hotel On North
Hotel On North3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (982 reviews)
9.6/10
Exceptional
(982 reviews)
"Very nice hotel"
"Very nice hotel"Philip




5. Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel3.0 star property
North Adams
9.0 out of 10, Wonderful, (1,006 reviews)
9.0/10
Wonderful
(1,006 reviews)
"Had a great time at this wonderful hotel."
"Had a great time at this wonderful hotel."marwan




6. The Red Lion Inn
The Red Lion Inn3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,013 reviews)
8.8/10
Excellent
(1,013 reviews)
"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."
"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."Lisabeth




7. Berkshires Untold
Berkshires Untold3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,070 reviews)
9.0/10
Wonderful
(1,070 reviews)
"Very nice place beautiful view"
"Very nice place beautiful view"Brian




8. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel3.0 star property
Lee
9.2 out of 10, Wonderful, (1,001 reviews)
9.2/10
Wonderful
(1,001 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"Gustavo




9. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,003 reviews)
9.4/10
Exceptional
(1,003 reviews)
"Lovely room, comfortable bed and a nice breakfast."
"Lovely room, comfortable bed and a nice breakfast."judith




10. Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort3.0 star property
Hancock
8.4 out of 10, Very good, (1,004 reviews)
8.4/10
Very good
(1,004 reviews)
"Nice resort and friendly staff."
"Nice resort and friendly staff."Olga




11. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires3.0 star property
Lenox
9.2 out of 10, Wonderful, (689 reviews)
9.2/10
Wonderful
(689 reviews)
"Great stay!"
"Great stay!"Vandhana




12. The Porches Inn at Mass MoCA
The Porches Inn at Mass MoCA3.5 star property
North Adams
9.4 out of 10, Exceptional, (530 reviews)
9.4/10
Exceptional
(530 reviews)
"Great stay"
"Great stay"Ram




13. Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott Williamstown3.0 star property
Williamstown
8.8 out of 10, Excellent, (441 reviews)
8.8/10
Excellent
(441 reviews)
"Nicer than your average ~$150 hotels. Clean room, but the details were better than the local Holiday Inn, etc. Would stay again."
"Nicer than your average ~$150 hotels. Clean room, but the details were better than the local Holiday Inn, etc. Would stay again."Josh




14. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
9.6/10
Exceptional
(51 reviews)
"Clean, spacious room
Accommodating staff especially Shawn and Jennifer at the front desk.
Very nice pool and gym
Definitely coming back"
"Clean, spacious room
Accommodating staff especially Shawn and Jennifer at the front desk.
Very nice pool and gym
Definitely coming back"Francis




15. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG3.0 star property
Pittsfield
7.8 out of 10, Good, (1,001 reviews)
7.8/10
Good
(1,001 reviews)
"enjoyed our stay"
"enjoyed our stay"Mark




16. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (717 reviews)
9.2/10
Wonderful
(717 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
"Great place to stay. Great staff and convenient location. Nice restaurant as well."James




17. The Ponds at Foxhollow
The Ponds at Foxhollow3.0 star property
Lenox
8.4 out of 10, Very good, (157 reviews)
8.4/10
Very good
(157 reviews)
"liked it was clean . furniture is dated. Roads need repair . too many potholes"
"liked it was clean . furniture is dated. Roads need repair . too many potholes"Anthony




18. Blooming Inn
Blooming Inn3.0 star property
Shelburne Falls
9.2 out of 10, Wonderful, (151 reviews)
9.2/10
Wonderful
(151 reviews)
"Like the ambiance as well as the decor! The location was perfect for walking around town!"
"Like the ambiance as well as the decor! The location was perfect for walking around town!"Robert




19. The Revival House
The Revival House3.0 star property
Adams
9.0 out of 10, Wonderful, (46 reviews)
9.0/10
Wonderful
(46 reviews)
"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




20. Inn at Silver Maple Farm
Inn at Silver Maple Farm3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
9.8/10
Exceptional
(118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"Linda
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




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




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




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




Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
10/10 Excellent
Great place!
Great place!
Ann




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




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




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




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




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




The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
10/10 Excellent
A dog barking during the night
A dog barking during the night
Sheila




The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The BerkshiresLenox
10/10 Excellent
VERY friendly staff and location for area attractions.
VERY friendly staff and location for area attractions.
Lawrence




Fairfield Inn & Suites by Marriott Williamstown
Fairfield Inn & Suites by Marriott WilliamstownWilliamstown
10/10 Excellent
The staff were all friendly and the hotel was clean and fresh!
The staff were all friendly and the hotel was clean and fresh!
Diane




Blooming Inn
Blooming InnShelburne Falls
10/10 Excellent
The Blooming Inn was great.
Very clean. Great old house.
Loved the motion sensor lights when you walk in later at night. Also the charging cords for phones and tablets is a nice touch.
Great toilet paper!!!
The Blooming Inn was great.
Very clean. Great old house.
Loved the motion sensor lights when you walk in later at night. Also the charging cords for phones and tablets is a nice touch.
Great toilet paper!!!
Philip M




Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
10/10 Excellent
One of the best hotel i been in my life. Everyone that works there is so friendly. From the front desk to the restaurant are amazing. The food is delicious and the pool is beautiful and the entire hotel is clean. I went from staying from one day to three days.
One of the best hotel i been in my life. Everyone that works there is so friendly. From the front desk to the restaurant are amazing. The food is delicious and the pool is beautiful and the entire hotel is clean. I went from staying from one day to three days.
Gipsy




Brook Farm Inn
Brook Farm InnLenox
10/10 Excellent
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
roberta




Inn at Silver Maple Farm
Inn at Silver Maple FarmEast Chatham
10/10 Excellent
This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!
This is a super clean, comfortable, and relaxing Inn. The Inn-keepers, Chloe and Shawn are wonderful. I could not have been happier with the service, the level of cleanliness, and the comfort of my room and common areas. Breakfast was delicious!
Michelle




Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the BerkshiresSouth Lee
10/10 Excellent
I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...
I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...
David




Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
10/10 Excellent
Everything there was great except Christiansens taver. The service was ok but the food was terrible. I would not recommend this place for dining. I would go to McDonalds before I ate there again. We do however recommend Powder Hounds Tavern at the entrance, The service and the food were excellent and affordable.
Everything there was great except Christiansens taver. The service was ok but the food was terrible. I would not recommend this place for dining. I would go to McDonalds before I ate there again. We do however recommend Powder Hounds Tavern at the entrance, The service and the food were excellent and affordable.
Lloyd A.
