Title: Visit Windsor: 2026 Travel Guide for Windsor, Massachusetts | Expedia.com [Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6005427.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d6005427.Destination-Travel-Guides) # Windsor, MA ## Travel Guide ## Visit Windsor - Windsor Hotel Deals - Vacation Rentals in Windsor ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/d239029a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St North Adams MA Fully refundable $135 nightly $151 total Apr 28 - Apr 29 Total with taxes and fees Book a stay at this business-friendly hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ... 8.8/10 Excellent! (1,001 reviews) Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ... Reviewed on Mar 22, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F28%2F2026&endDate=4%2F29%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=6005427) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA $108 nightly $120 total Apr 26 - Apr 27 Total with taxes and fees Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ... 9/10 Wonderful! (888 reviews) very clean and friendly staff Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005427) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshires Untold 194 Pittsfield Rd Lenox MA $78 nightly $87 total Mar 29 - Mar 30 Total with taxes and fees Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ... 9/10 Wonderful! (881 reviews) Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, ... Reviewed on Mar 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=76297618&PinnedHotelID=76297618&HadPinnedHotel=true®ionId=6005427) [See all 1,004 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6005427) 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. ![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Huttopia Berkshires 312 Kittle Rd Williamstown MA Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ... 9.4/10 Exceptional! (10 reviews) Excelente servicio Reviewed on Mar 8, 2026 [](https://expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jiminy Peak Mountain Resort 37 Corey Rd Hancock MA Book a stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ... [](https://expedia.com/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Ponds at Foxhollow 3 Foxhollow Drive Route 7 Lenox MA Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ... 8.6/10 Excellent! (141 reviews) I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ... Reviewed on Feb 9, 2026 [](https://expedia.com/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) [See all properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6005427&sort=VACATION_RENTAL) 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. ## Check Windsor hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-03-28&endDate=2026-03-29)[Mar 28 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-03-28&endDate=2026-03-29) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-03-29&endDate=2026-03-30)[Mar 29 - Mar 30](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-03-29&endDate=2026-03-30) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) ## Cities near Windsor ![Wahconah Falls in the Berkshires](https://images.trvl-media.com/place/6911/0d61b065-dfb2-41c6-8d5b-cded88165403.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Dalton ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Cheshire ![Hinsdale](https://images.trvl-media.com/place/6005406/994d4472-5b99-4b6b-8148-12426b4c9b53.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Hinsdale ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Hotels.0-l553248621532665297-0.Travel-Guide-Filter-Hotels) - [Savoy Hotels ](https://www.expedia.com/Savoy-Hotels.d6005417.Travel-Guide-Hotels) - [Cabin Rentals in Savoy ](https://www.expedia.com/Savoy-Cabins.d6005417-aaCabins.Travel-Guide-Accommodation) - [B&B in Savoy ](https://www.expedia.com/Savoy-Bed-And-Breakfast.d6005417-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Savoy ](https://www.expedia.com/Savoy-Cottages.d6005417-aaCottages.Travel-Guide-Accommodation) - [Peru Hotels ](https://www.expedia.com/Peru-Hotels.d553248634999167831.Travel-Guide-Hotels) - [Hotels near Bas Ridge Golf Course ](https://www.expedia.com/Bas-Ridge-Golf-Course-Hotels.0-l553248621560926698-0.Travel-Guide-Filter-Hotels) - [Hinsdale Hotels ](https://www.expedia.com/Hinsdale-Hotels.d6005406.Travel-Guide-Hotels) - [5 Star Hotels in Hinsdale ](https://www.expedia.com/5Star-Hinsdale-Hotels.s50-0-d6005406.Travel-Guide-Filter-Hotels) - 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Anthony Birthplace Museum ](https://www.expedia.com/Susan-B-Anthony-Birthplace-Museum-Hotels.0-l553248621532666696-0.Travel-Guide-Filter-Hotels) - [Hotels near Tannery Falls ](https://www.expedia.com/Tannery-Falls-Hotels.0-l553248621560941221-0.Travel-Guide-Filter-Hotels) - [Cummington Hotels ](https://www.expedia.com/Cummington-Hotels.d183324.Travel-Guide-Hotels) - [B&B in Cummington ](https://www.expedia.com/Cummington-Bed-And-Breakfast.d183324-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Cummington ](https://www.expedia.com/Cummington-Cabins.d183324-aaCabins.Travel-Guide-Accommodation) - [4 Star Hotels in Cummington ](https://www.expedia.com/4Star-Cummington-Hotels.s40-0-d183324.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Cummington ](https://www.expedia.com/5Star-Cummington-Hotels.s50-0-d183324.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Cummington ](https://www.expedia.com/3Star-Cummington-Hotels.s30-0-d183324.Travel-Guide-Filter-Hotels) - [Motels in Cummington ](https://www.expedia.com/Cummington-Motels.d183324-aaMotels.Travel-Guide-Accommodation) - [Adams Hotels ](https://www.expedia.com/Adams-Hotels.d6005393.Travel-Guide-Hotels) - [B&B in Adams ](https://www.expedia.com/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Apartments in Adams ](https://www.expedia.com/Adams-Apartments.d6005393-aaApartments.Travel-Guide-Accommodation) - [Resorts & Hotels with Spas in Adams ](https://www.expedia.com/Adams-Hotels-Spa-Hotel.0-0-d6005393-tSpaHotel.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Adams ](https://www.expedia.com/Adams-Cabins.d6005393-aaCabins.Travel-Guide-Accommodation) - [Hotels with Restaurants in Adams ](https://www.expedia.com/Adams-Hotels-Hotels-With-Restaurants.0-0-d6005393-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [Cottages in Adams ](https://www.expedia.com/Adams-Cottages.d6005393-aaCottages.Travel-Guide-Accommodation) - [Motels in Adams ](https://www.expedia.com/Adams-Motels.d6005393-aaMotels.Travel-Guide-Accommodation) - [Ski Hotels in Adams ](https://www.expedia.com/Adams-Hotels-Ski-Hotel.0-0-d6005393-tSkiHotel.Travel-Guide-Filter-Hotels) - [Resorts in Adams ](https://www.expedia.com/Adams-Resorts.d6005393-aaResorts.Travel-Guide-Accommodation) - [Condo Rentals in Adams ](https://www.expedia.com/Adams-Condos.d6005393-aaCondos.Travel-Guide-Accommodation) - [Flights to Savoy ](https://www.expedia.com/Cheap-Flights-To-Savoy.d6005417.Travel-Guide-Flights) - [Flights to Hinsdale ](https://www.expedia.com/Cheap-Flights-To-Hinsdale.d6005406.Travel-Guide-Flights) - [Flights to Dalton ](https://www.expedia.com/Cheap-Flights-To-Dalton.d6911.Travel-Guide-Flights) - [Flights from Plainfield ](https://www.expedia.com/lp/flights/6005414/flights-from-plainfield) - [Flights to Plainfield ](https://www.expedia.com/Cheap-Flights-To-Plainfield.d6005414.Travel-Guide-Flights) - [Flights to Cheshire ](https://www.expedia.com/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights) - [Flights to Cummington ](https://www.expedia.com/Cheap-Flights-To-Cummington.d183324.Travel-Guide-Flights) - [Flights to Adams ](https://www.expedia.com/Cheap-Flights-To-Adams.d6005393.Travel-Guide-Flights) - [Flights from Adams ](https://www.expedia.com/lp/flights/6005393/flights-from-adams) - [Visit Savoy ](https://www.expedia.com/Savoy.dx6005417) - [Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Dalton.d553248621532665297.Vacation-Attraction) - [Visit Hinsdale ](https://www.expedia.com/Hinsdale.dx6005406) - [Visit Dalton ](https://www.expedia.com/Dalton.dx6911) - [Visit Plainfield ](https://www.expedia.com/Plainfield.dx6005414) - [Hinsdale Vacations ](https://www.expedia.com/Hinsdale.d6005406.Destination-Travel-Guides) - [Visit Cheshire ](https://www.expedia.com/Cheshire.dx6005398) - [Dalton Vacations ](https://www.expedia.com/Dalton.d6911.Destination-Travel-Guides) - [Plainfield Vacations ](https://www.expedia.com/Plainfield.d6005414.Destination-Travel-Guides) - [Savoy Mountain State Forest ](https://www.expedia.com/Savoy-Mountain-State-Forest-Massachusetts.d6339858.Vacation-Attraction) - [Susan B. Anthony Birthplace Museum ](https://www.expedia.com/Susan-B-Anthony-Birthplace-Museum-Adams.d553248621532666696.Vacation-Attraction) - [Tannery Falls ](https://www.expedia.com/Tannery-Falls-Savoy.d553248621560941221.Vacation-Attraction) - [Visit Cummington ](https://www.expedia.com/Cummington.dx183324) - [Visit Adams ](https://www.expedia.com/Adams.dx6005393) - [Cummington Vacations ](https://www.expedia.com/Cummington.d183324.Destination-Travel-Guides) - [Visit Lanesborough ](https://www.expedia.com/Lanesborough.dx6005408) - [Adams Vacations ](https://www.expedia.com/Adams.d6005393.Destination-Travel-Guides) - [Visit Hawley ](https://www.expedia.com/Hawley.dx3000438704) - [Car rentals near Savoy ](https://www.expedia.com/Car-Rentals-In-Savoy.d6005417.Car-Rental-Guide) - [Car rentals near Peru ](https://www.expedia.com/Car-Rentals-In-Peru.d553248634999167831.Car-Rental-Guide) - [Car rentals near Hinsdale ](https://www.expedia.com/Car-Rentals-In-Hinsdale.d6005406.Car-Rental-Guide) - [Car rentals near Dalton ](https://www.expedia.com/Car-Rentals-In-Dalton.d6911.Car-Rental-Guide) - [Car rentals near Plainfield ](https://www.expedia.com/Car-Rentals-In-Plainfield.d6005414.Car-Rental-Guide) - [Car rentals near Cheshire ](https://www.expedia.com/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide) - [Car rentals near Savoy Mountain State Forest ](https://www.expedia.com/Car-Rentals-In-Savoy-Mountain-State-Forest.d6339858.Car-Rental-Guide) - [Car rentals near Cummington ](https://www.expedia.com/Car-Rentals-In-Cummington.d183324.Car-Rental-Guide) - [Car rentals near Adams ](https://www.expedia.com/Car-Rentals-In-Adams.d6005393.Car-Rental-Guide) - [Savoy Vacation Rentals ](https://www.expedia.com/Savoy-Vacation-Rentals.d6005417.Travel-Guide-VacationRentals) - [Hinsdale Vacation Rentals ](https://www.expedia.com/Hinsdale-Vacation-Rentals.d6005406.Travel-Guide-VacationRentals) - [Dalton Vacation Rentals ](https://www.expedia.com/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals) - [Cheshire Vacation Rentals ](https://www.expedia.com/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals) - [Cummington Vacation Rentals ](https://www.expedia.com/Cummington-Vacation-Rentals.d183324.Travel-Guide-VacationRentals) - Cities near Windsor - Places of interest [Dalton](https://expedia.com/Dalton.dx6911)[Cummington](https://expedia.com/Cummington.dx183324)[Cheshire](https://expedia.com/Cheshire.dx6005398)[Hinsdale](https://expedia.com/Hinsdale.dx6005406)[Plainfield](https://expedia.com/Plainfield.dx6005414)[Savoy](https://expedia.com/Savoy.dx6005417) - [Tanglewood Music Center ](https://expedia.com/Tanglewood-Music-Center-Lenox.d503292.Vacation-Attraction) - [National Shrine of the Divine Mercy ](https://expedia.com/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) - [Jiminy Peak Mountain Resort ](https://expedia.com/Jiminy-Peak-Mountain-Resort-Hancock.d553248621532665536.Vacation-Attraction) - [Williams College ](https://expedia.com/Williams-College-Williamstown.d6091833.Vacation-Attraction) - [Green Mountain National Forest ](https://expedia.com/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction) - [Norman Rockwell Museum ](https://expedia.com/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Massachusetts Museum of Contemporary Art ](https://expedia.com/Massachusetts-Museum-Of-Contemporary-Art-North-Adams.d6091827.Vacation-Attraction) - [Berkshire East Ski Resort ](https://expedia.com/Berkshire-East-Ski-Resort-Charlemont.d553248621532666707.Vacation-Attraction) - [The Mount ](https://expedia.com/The-Mount-Lenox.d553248621532665265.Vacation-Attraction) - [The Clark Art Institute ](https://expedia.com/The-Clark-Art-Institute-Williamstown.d553248621533116688.Vacation-Attraction) - [Hancock Shaker Village ](https://expedia.com/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Lee Premium Outlets ](https://expedia.com/Lee-Premium-Outlets-Lee.d6127084.Vacation-Attraction) - [Jacob's Pillow ](https://expedia.com/Jacobs-Pillow-Becket.d553248621532666599.Vacation-Attraction) - [Mount Greylock ](https://expedia.com/Mount-Greylock-Adams.d6091829.Vacation-Attraction) - [Bousquet Ski Area ](https://expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction) - [Bridge of Flowers ](https://expedia.com/Bridge-Of-Flowers-Shelburne-Falls.d553248621532666724.Vacation-Attraction) - [Williamstown Theatre Festival ](https://expedia.com/Williamstown-Theatre-Festival-Williamstown.d553248621532665542.Vacation-Attraction) - [Naumkeag Museum ](https://expedia.com/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) - [Wyndhurst Golf & Club ](https://expedia.com/Wyndhurst-Golf-Club-Lenox.d553248621532665266.Vacation-Attraction) - [Berkshire Botanical Garden ](https://expedia.com/Berkshire-Botanical-Garden-Stockbridge.d553248621532665247.Vacation-Attraction) - [Shakespeare and Company ](https://expedia.com/Shakespeare-And-Company-Lenox.d6127086.Vacation-Attraction) - [Taconic Golf Club ](https://expedia.com/Taconic-Golf-Club-Williamstown.d553248621561173642.Vacation-Attraction) - [Ventfort Hall Mansion and Gilded Age Museum ](https://expedia.com/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction) - [Natural Bridge State Park ](https://expedia.com/Natural-Bridge-State-Park-North-Adams.d553248621560926711.Vacation-Attraction) - [Goose Pond Reservation ](https://expedia.com/Goose-Pond-Reservation-Lee.d6339855.Vacation-Attraction) - [Berkshire Museum ](https://expedia.com/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) - [Harriman Reservoir ](https://expedia.com/Harriman-Reservoir-Vermont.d762079879267004416.Vacation-Attraction) - [Zoar Outdoor/Deerfield Valley Canopy Tours ](https://expedia.com/Zoar-OutdoorDeerfield-Valley-Canopy-Tours-Charlemont.d553248621561930011.Vacation-Attraction) - [Mount Greylock State Reservation Visitor Center ](https://expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction) - [Colonial Theater ](https://expedia.com/Colonial-Theater-Pittsfield.d553248621532665289.Vacation-Attraction)