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 ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd Williamstown MA $126 nightly $141 total Feb 22 - Feb 23 Total with taxes and fees Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6005427) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundable $121 nightly $136 total Mar 10 - Mar 11 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! (826 reviews) Room was clean and nicely equipped with kitchen. Will return if the future. Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005427) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Williams Inn 101 Spring Street Williamstown MA $189 nightly $212 total Mar 11 - Mar 12 Total with taxes and fees Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ... 9.6/10 Exceptional! (572 reviews) Clean Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F11%2F2026&endDate=3%2F12%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=6005427) [See all 990 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F10%2F2026&endDate=2%2F11%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. ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd Williamstown MA Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on Feb 3, 2026 [](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![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 ... 9.2/10 Wonderful! (8 reviews) Healthy food too! Reviewed on Oct 20, 2025 [](https://expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4_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 The Mount and Wyndhurst Golf & Club are located ... 8.4/10 Very Good! (140 reviews) Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned. Reviewed on Jan 3, 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=2026-02-09&endDate=2026-02-10)[Feb 9 - Feb 10](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-02-09&endDate=2026-02-10) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-02-10&endDate=2026-02-11)[Feb 10 - Feb 11](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2026-02-10&endDate=2026-02-11) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2%2F20%2F2026&endDate=2%2F22%2F2026)[Feb 20 - Feb 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005427&startDate=2%2F20%2F2026&endDate=2%2F22%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 ![Had to wait on the light to get just right...totality worth it!!! #InStone](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) - 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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 from Sacramento to Cheshire ](https://www.expedia.com/lp/flights/180049/6005398/sacramento-to-cheshire) - [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) - [Jiminy Peak Mountain Resort ](https://expedia.com/Jiminy-Peak-Mountain-Resort-Hancock.d553248621532665536.Vacation-Attraction) - [Tanglewood Music Center ](https://expedia.com/Tanglewood-Music-Center-Lenox.d503292.Vacation-Attraction) - [Williams College ](https://expedia.com/Williams-College-Williamstown.d6091833.Vacation-Attraction) - [National Shrine of the Divine Mercy ](https://expedia.com/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) - [Green Mountain National Forest ](https://expedia.com/Green-Mountain-National-Forest-Vermont.d6115904.Vacation-Attraction) - [Berkshire East Ski Resort ](https://expedia.com/Berkshire-East-Ski-Resort-Charlemont.d553248621532666707.Vacation-Attraction) - [Massachusetts Museum of Contemporary Art ](https://expedia.com/Massachusetts-Museum-Of-Contemporary-Art-North-Adams.d6091827.Vacation-Attraction) - [Norman Rockwell Museum ](https://expedia.com/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Mount Greylock ](https://expedia.com/Mount-Greylock-Adams.d6091829.Vacation-Attraction) - [The Clark Art Institute ](https://expedia.com/The-Clark-Art-Institute-Williamstown.d553248621533116688.Vacation-Attraction) - [Lee Premium Outlets ](https://expedia.com/Lee-Premium-Outlets-Lee.d6127084.Vacation-Attraction) - [Bousquet Ski Area ](https://expedia.com/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction) - [Jacob's Pillow ](https://expedia.com/Jacobs-Pillow-Becket.d553248621532666599.Vacation-Attraction) - [The Mount ](https://expedia.com/The-Mount-Lenox.d553248621532665265.Vacation-Attraction) - [Berkshire Botanical Garden ](https://expedia.com/Berkshire-Botanical-Garden-Stockbridge.d553248621532665247.Vacation-Attraction) - [Hancock Shaker Village ](https://expedia.com/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Wyndhurst Golf & Club ](https://expedia.com/Wyndhurst-Golf-Club-Lenox.d553248621532665266.Vacation-Attraction) - [Naumkeag Museum ](https://expedia.com/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) - [Natural Bridge State Park ](https://expedia.com/Natural-Bridge-State-Park-North-Adams.d553248621560926711.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) - [Deerfield River ](https://expedia.com/Deerfield-River-United-States-of-America.d682156682122641408.Vacation-Attraction) - [Mount Greylock State Reservation Visitor Center ](https://expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction) - 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[Shakespeare and Company ](https://expedia.com/Shakespeare-And-Company-Lenox.d6127086.Vacation-Attraction)