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Our top choices for Windsor cottages
1. The Cottage on Mill Brook is walking distance to Berkshire East and the River.
The Cottage on Mill Brook is walking distance to Berkshire East and the River.Charlemont
$555 nightly
The price is $620
$620 total
Nov 13 - Nov 14
Total with taxes and fees
2. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck3.0 star property
Stephentown
$529 nightly
The price is $587
$587 total
Nov 11 - Nov 12
Total with taxes and fees
3. Berkshires farm, 30+ guests, 50 acres
Berkshires farm, 30+ guests, 50 acresNew Lebanon
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
$1,881 nightly
The price is $1,899
$1,899 total
Nov 18 - Nov 19
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top reviews in Windsor
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
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
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
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
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
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
Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
10/10 Excellent
Solid
Solid
Colton
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
The Central Downtown Inn & Suites
The Central Downtown Inn & SuitesPittsfield
10/10 Excellent
Beautiful room, very conveniently located right next to a main strip of little shops, theaters and restaurants. We brought all of our own food and were able to store it safely, roomy refrigerator provided- and all cooking utensils, pots, pans, plates... Everything provided. There was a dvd player, and we were able to have movie nights, and a back balcony to enjoy coffee on the porch or read a book in a heavily wooded area which provided a nice shady view to block the parking lot. The front desk...
Beautiful room, very conveniently located right next to a main strip of little shops, theaters and restaurants. We brought all of our own food and were able to store it safely, roomy refrigerator provided- and all cooking utensils, pots, pans, plates... Everything provided. There was a dvd player, and we were able to have movie nights, and a back balcony to enjoy coffee on the porch or read a book in a heavily wooded area which provided a nice shady view to block the parking lot. The front desk...
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
Hotel Downstreet, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection HotelNorth Adams
10/10 Excellent
Great place!
Great place!
Ann
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
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
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
Frequently Asked Questions
How much do cottages in Windsor cost?
Cottages in Windsor range between $587 and $1,898 per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Windsor with Expedia?
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