Find hotels in Windsor, MA from $85

Top reasons to visit Windsor

• Outdoor Adventure: Windsor is a haven for outdoor enthusiasts, offering skiing, breathtaking mountain views, and nearby nature reserves.
• Wellness Retreats: After an active day, unwind at local wellness centers for a rejuvenating experience.
• Scenic Wine Country: Explore charming local wineries that provide a romantic atmosphere and stunning vistas.
• Diverse Accommodations: Choose from cozy motels to inviting resorts, perfect for families and couples alike.
• Year-Round Activities: Enjoy a mix of thrilling winter sports and peaceful summer escapes in this picturesque area.

Find great hotels near Windsor

Discover the charm of Windsor, Massachusetts, with a range of hotel accommodations designed for every type of traveler. From cozy motels to inviting resorts, you'll find the perfect spot for family getaways, romantic retreats, or thrilling ski vacations. Explore our top-rated hotels, read reviews, and enjoy a memorable stay in this picturesque area.

• Holiday Inn & Suites Pittsfield-Berkshires by IHG: This 3-star hotel offers a unique blend of business and leisure, making it an ideal choice for travelers seeking a professional yet welcoming atmosphere. Located 11 miles from Windsor, it features a fully-equipped Business Center with 24-hour access, meeting rooms, and a conference center. The hotel's commitment to inclusivity is evident, as it is LGBTQIA-friendly and affiliated with LGBTQI travel guides. Guests can also indulge in nearby winery experiences, adding a delightful touch to their stay.
• Berkshire Mountain Lodge: Nestled 13 miles from Windsor, this 3-star lodge is perfect for adventure enthusiasts and ski lovers. With easy access to ski shuttles and lifts, guests can hit the slopes with ease. The lodge offers golf experiences and a range of adventure sports, including biking, kayaking, and ziplining. Its proximity to nature trails and snow tubing locations ensures that every guest can find an exciting outdoor activity to enjoy during their stay.
• Club Wyndham Bentley Brook: Located 13 miles from Windsor, this 3-star hotel is a haven for adventure seekers and winter sports fans. With close access to ski shuttles and lifts, guests can partake in downhill and cross-country skiing, as well as snowboarding right onsite. The property also provides hiking and biking opportunities nearby, making it a great choice for those looking to immerse themselves in the stunning Berkshire outdoors. The welcoming atmosphere and recreational facilities ensure a memorable stay for all guests.

Where to stay near Windsor

Windsor, Massachusetts, offers an exciting blend of adventure and scenic beauty, perfect for outdoor enthusiasts and families alike. Explore the nearby wine country with local wineries that provide a romantic atmosphere and stunning views. Whether you're seeking a thrilling ski vacation or a peaceful escape, Windsor and its surrounding areas cater to all types of travelers, making it an ideal destination for unforgettable experiences.

• Pittsfield: Located 11 miles from Windsor, Pittsfield is a vibrant city nestled in the heart of the Berkshires. Known for its year-round appeal, the city attracts visitors especially during the summer months from June to August. Outdoor enthusiasts flock to Pittsfield for thrilling ski experiences, with access to top-notch ski fields and resorts. Beyond skiing, the area boasts beautiful lakes and mountains ideal for hiking and relaxation. Families can also enjoy local waterparks, making Pittsfield a great destination for all ages.
• North Adams: Situated 14 miles away from Windsor, North Adams is a charming city that invites adventure seekers and outdoor lovers alike. With visitor numbers peaking in June, July, and September, this city offers an array of outdoor activities, including skiing at nearby resorts. Art lovers will appreciate the local art museum and vibrant public art scene, which reflect the city’s cultural richness. North Adams is perfect for those looking to combine outdoor exploration with artistic experiences.
• Savoy: Just 4 miles from Windsor, Savoy is a quaint city known for its scenic beauty and outdoor adventures. Popular among visitors from March to April and in July, Savoy offers excellent skiing opportunities and access to stunning mountain peaks and serene lakes. This small town is ideal for nature lovers and those looking to escape the hustle and bustle, providing a peaceful retreat amid picturesque landscapes. Whether you're skiing or hiking, Savoy has something for every outdoor enthusiast.

Things to do near Windsor

Windsor, Massachusetts, is a fantastic destination for adventure seekers and outdoor enthusiasts, offering thrilling activities like skiing at its local ski fields and resorts. In addition to winter sports, visitors can unwind at wellness centers to rejuvenate after an adventurous day. Whether you're hitting the slopes or relaxing, Windsor provides a perfect blend of excitement and relaxation for your vacation.

Shopping

In Windsor, you can enjoy shopping at Guido's Marketplace, a public market offering a variety of goods. If you're up for a drive, visit North Adams Center and North Adams Gateway Center, both just 13 and 14 miles away, featuring family-friendly shopping experiences in a vibrant setting.

Recreation

At Bas Ridge Golf Course, enjoy a day of golfing surrounded by beautiful landscapes just 6 miles from Windsor. For a serene escape, visit Windsor Lake Park, 12 miles away, where you can relax by the water and immerse yourself in nature. Skyline Country Club offers another excellent golfing experience just 10 miles from town.

Adventure

Experience the thrill of winter sports at Jiminy Peak Mountain Resort, located 13 miles from Windsor. For a diverse range of outdoor activities, visit Berkshire East Ski Resort, 12 miles away. Enjoy picturesque views and challenging trails at Skyline Trail, just 10 miles away, perfect for hiking enthusiasts.

Nightlife

Experience the vibrant nightlife in Windsor by catching a show at the nearby Adams Theater or Colonial Theater, both offering a mix of culture and romance. For a unique experience, check out the Barrington Stage Company, where you can enjoy captivating performances in a welcoming atmosphere.

Booking tips and Expedia advantages for Windsor

To save money during your trip to Windsor, consider visiting in January or March to April when hotel prices are lower. Tuesdays offer the cheapest stays, while Saturdays are the most expensive. Use Expedia’s search tool to compare room rates and find budget-friendly accommodations, and consider bundling your hotel, flights, and activities for additional savings. Joining Expedia's One Key membership can provide exclusive discounts and cash back on future stays. Lastly, take advantage of free local activities and explore the area on foot to further reduce costs.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Windsor are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Windsor is Tuesday. The most expensive day to stay in Windsor is Saturday.
• Find cheap hotels on Expedia: Expedia’s search tool lets you set your budget, choose your desired location, and much more. You can arrange your search results by price, from lowest to highest, ensuring you spot the most affordable hotels at the top. Additionally, you have the option to refine your choices by hotel category; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking.
• Consider bundling your trip: You can save money by combining your Windsor hotel reservation with your flights and activities through an Expedia package deal.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Windsor

Windsor, Massachusetts, is a fantastic destination for outdoor enthusiasts and adventure seekers. Visitors can enjoy breathtaking mountain views, explore nearby nature reserves, and experience the thrill of skiing. The area offers a diverse range of attractions that cater to those looking for adventure, cultural experiences, and outdoor activities, making it an ideal spot for a memorable vacation.

• Mount Greylock: Experience breathtaking views from the highest peak in Massachusetts, located 11 miles from Windsor. Outdoor enthusiasts can hike scenic trails that showcase the stunning natural beauty of the Berkshires, making it a perfect spot for adventure seekers.
• Wahconah Falls State Park: Just 4 miles from Windsor, this park features picturesque waterfalls and lush landscapes. Enjoy hiking and exploring the scenic trails while taking in the refreshing sounds of nature, ideal for those looking for an outdoor adventure.
• Berkshire East Ski Resort: Located 12 miles away, this ski resort offers thrilling winter sports opportunities. Whether skiing, snowboarding, or enjoying the beautiful mountain scenery, it's a must-visit for adventure lovers year-round.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	19.9°F (-6.7°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
February	22.1°F (-5.5°C)	Light Rain	Mostly Cloudy	Moderately Low	Average
March	29.7°F (-1.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	41.4°F (5.2°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
May	53.8°F (12.1°C)	Light Rain	Mostly Sunny	Average	Average
June	61.5°F (16.4°C)	Light Rain	Mostly Sunny	Average	Average
July	67.6°F (19.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	65.7°F (18.7°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly High
September	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Average	Average
October	47.7°F (8.7°C)	Light Rain	Mostly Cloudy	Moderately High	Slightly High
November	35.4°F (1.9°C)	Light Rain	Mostly Sunny	Moderately High	Average
December	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

The nearest major airports for your trip to Windsor

To reach Windsor, Massachusetts, you have several airport options. Hartford, CT's Bradley International Airport (BDL) is 44 miles away, with nearby accommodations like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport, and the Simsbury 1820 House, 7 miles away. Albany, NY's Albany International Airport (ALB) is 42 miles from Windsor, offering hotel choices such as the Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 8 miles from the airport. Additionally, Pittsfield Municipal Airport (PSF) is the closest, located 14 miles away, with options like The Stockbridge Country Inn and The Central Downtown Inn & Suites nearby.