Find hotels in Windsor, MA from $88

Top reasons to visit Windsor

• Outdoor Adventures: Windsor is a paradise for outdoor enthusiasts, offering skiing, hiking, and breathtaking scenery in nature reserves and mountains.
• Windsor Wine Country: Savor delightful wine tastings in the picturesque Windsor Wine Country, perfect for a relaxing day.
• Charming Accommodations: Enjoy a variety of lodging options, from cozy bed & breakfasts to relaxing resorts, catering to all travelers.
• Family-Friendly Activities: Windsor offers family-friendly attractions and picnic spots, making it ideal for vacations with loved ones.
• Vibrant Local Culture: Explore nearby downtown Healdsburg for a romantic atmosphere and diverse dining experiences.

Find great hotels near Windsor

Explore a range of delightful hotel accommodations in Windsor, Massachusetts, perfect for families, couples, and adventure seekers alike. Whether you're looking for a cozy bed & breakfast or a relaxing resort, Windsor offers various lodging options to suit your needs. Enjoy a memorable vacation experience with well-appointed suites and convenient access to local attractions. Start planning your getaway in this charming town today.

• Berkshire Mountain Lodge: Berkshire Mountain Lodge is a charming 3-star lodge with a guest rating of 9.0, ideal for those seeking an adventurous vacation in the picturesque Berkshires. Located 13 miles from Windsor, this lodge is perfect for ski enthusiasts and golfers alike. With access to ski shuttles and lifts nearby, guests can enjoy exhilarating winter sports. For the summer adventurers, activities like kayaking, ziplining, and biking rentals are available nearby. The lodge also features on-site golf experiences, making it a versatile choice for those looking to immerse themselves in outdoor recreation year-round.
• Holiday Inn & Suites Pittsfield-Berkshires by IHG: Holiday Inn & Suites Pittsfield-Berkshires by IHG is a welcoming 3-star hotel rated at 8.0, situated 11 miles from Windsor. This family-friendly hotel caters to adventurous spirits, offering a range of activities such as cross-country skiing, fishing, and horse riding in the nearby area. With amenities tailored for children, including free cribs and breakfast options, it ensures a comfortable stay for families. The property is conveniently located near a winery vineyard, making it an excellent choice for those looking to explore local flavors while enjoying a blend of relaxation and adventure.
• Club Wyndham Bentley Brook: Club Wyndham Bentley Brook is a highly-rated 3-star hotel with a guest rating of 9.2, located 13 miles from Windsor. This property is a haven for ski lovers and adventure seekers, providing easy access to ski shuttles and lifts. Guests can enjoy on-site snowboarding and nearby cross-country skiing, as well as hiking opportunities. The inviting accommodations and excellent amenities make it a perfect retreat for those looking to indulge in winter sports while experiencing the breathtaking beauty of the Berkshires.

Where to stay near Windsor

Windsor, Massachusetts offers a perfect blend of outdoor adventure and scenic beauty, ideal for family-friendly vacations. Explore the charming local attractions, including the picturesque Windsor Wine Country, where you can indulge in delightful tastings. Nearby, the vibrant atmosphere of downtown Healdsburg invites you to enjoy its romantic ambiance and diverse dining options. Whether you're seeking an adventurous outing or a relaxing retreat, Windsor and its surroundings promise unforgettable experiences.

• Pittsfield: Located 11 miles from Windsor, Pittsfield is a vibrant city that offers an exciting mix of outdoor adventures and urban charm. Known for its skiing opportunities, visitors flock here during the peak months of June to August for thrilling sports experiences. With nearby ski resorts and fields, winter sports enthusiasts will find plenty to enjoy. The city's landscape is adorned with beautiful lakes and mountains, making it a picturesque destination year-round. Don't miss the local waterpark for family-friendly fun during the warmer months.
• Hancock: Just 12 miles from Windsor, Hancock is another great destination for outdoor lovers. The city sees increased visitor numbers from March to April and again in July, thanks to its excellent skiing facilities. Hancock is surrounded by stunning mountains and serene lakes, perfect for both adrenaline-seeking adventurers and those looking to unwind in nature. The urban parks here provide ample space for relaxation and picnics, making it a well-rounded spot for visitors seeking both adventure and tranquility.
• North Adams: Situated 14 miles away from Windsor, North Adams blends culture and outdoor activities seamlessly. With peak travel seasons in June to July and September, this city attracts those interested in adventurous pursuits and cultural experiences. Visitors can enjoy live music concerts and explore the local art museum and cultural center, adding a unique flair to their experience. The public art scattered throughout the city enhances its artistic vibe, making it a wonderful place to wander and soak in the creative atmosphere.

Things to do in Windsor

Windsor, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and stunning scenery. Visitors can enjoy skiing at nearby resorts and explore various ski fields. For a more relaxed experience, there are beautiful picnic spots where you can soak in the natural beauty of the area. Whether you're hitting the slopes or enjoying a leisurely day outdoors, Windsor offers a delightful escape for nature lovers and adventure seekers alike.

Shopping

In Windsor, you’ll find quaint shops offering unique gifts and local souvenirs. If you're up for a drive, head to the Lee Premium Outlets for brand-name bargains or explore the shops in nearby Great Barrington for a charming shopping experience.

Recreation

Experience tranquility at Kripalu Center for Yoga & Health, offering yoga classes and wellness workshops surrounded by nature. Explore the scenic hiking trails of the Berkshires for refreshing outdoor activities, or unwind with a soothing massage at a local spa to rejuvenate your mind and body.

Adventure

Explore Windsor State Forest for hiking and mountain biking amid picturesque landscapes and diverse wildlife. Try fishing or kayaking at nearby lakes for a refreshing outdoor experience. Don't miss the scenic views from the top of Mount Greylock, the highest peak in Massachusetts, offering thrilling adventures and stunning vistas.

Nightlife

In Windsor, Massachusetts, the nightlife is cozy and relaxed, featuring local pubs like The Windsor Tavern, where you can enjoy craft beers and live music. Nearby, outdoor events and seasonal festivals add to the vibrant atmosphere, making for a welcoming evening experience.

Booking tips and Expedia advantages for Windsor

• 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: Utilize Expedia's search tool to customize your preferences, such as your budget, desired location, and type of hotel you’re looking for. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by booking an Expedia package that combines your Windsor hotel stay with your flights and activities.

Find the best attractions near Windsor

Windsor, Massachusetts, is a haven for outdoor enthusiasts, offering stunning scenery and adventure opportunities. Explore its nature reserves and mountains, perfect for hiking and enjoying the great outdoors. Whether you're seeking thrilling adventures or a taste of local culture, Windsor's attractions promise memorable experiences for every traveler. Embrace the beauty and excitement of this charming destination.

• Massachusetts Museum of Contemporary Art: Experience the vibrant world of modern art at this expansive cultural center, showcasing innovative exhibitions and installations. The museum's unique architecture and engaging programming make it a must-visit for art enthusiasts.
• Mount Greylock: Embrace adventure at Massachusetts' highest peak, where breathtaking scenery awaits. Enjoy hiking trails, stunning views, and the thrill of outdoor activities, making it a perfect spot for nature lovers and thrill-seekers alike.
• Berkshire Museum: Discover a blend of art, history, and science at this family-friendly museum. With interactive exhibits and engaging programs, the Berkshire Museum offers a fun and educational experience for visitors of all ages.

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.

The nearest major airports for your trip to Windsor

When visiting Windsor, Massachusetts, you have several airport options. Hartford, CT (BDL-Bradley Intl.) is 44 miles away, with nearby hotels like the DoubleTree by Hilton Hartford - Bradley Airport, just 1 mile from the airport, and the Marriott Hartford Downtown, 12 miles away. ALBany, NY (ALB-Albany Intl.), located 42 miles from Windsor, offers accommodations such as The Landing Hotel at Rivers Casino & Resort and DoubleTree by Hilton Schenectady Downtown, both 8 miles from the airport. For those considering Manchester, NH (MHT-Manchester-Boston Regional), it's 87 miles away, featuring hotels like The Grand at Bedford Village Inn and DoubleTree by Hilton Manchester Downtown, both just 4 miles from the airport.