Find hotels in Windsor, MA from AED 256

Top reasons to visit Windsor

• Outdoor Adventures: Windsor is a haven for outdoor enthusiasts, offering skiing, hiking, and breathtaking scenic views.
• Charming Wineries: Discover local wineries nestled in picturesque wine country, perfect for tastings and relaxation.
• Wellness Centers: Unwind at wellness centers designed to enhance your vacation experience with relaxation and rejuvenation.
• Family-Friendly Atmosphere: The town provides a welcoming environment for families, featuring activities for all ages.
• Diverse Accommodations: Choose from various lodging options, including resorts and cozy motels, to suit your travel style.

Find great hotels near Windsor

Windsor, Massachusetts, offers a variety of hotel accommodations perfect for every type of traveler. Whether you’re seeking a family-friendly resort, a cozy motel, or a romantic getaway, you'll find options that cater to your needs. Enjoy a memorable ski vacation experience while exploring the area’s best hotels. With numerous reviews and ratings available, discovering the perfect lodging in Windsor has never been easier.

• Holiday Inn & Suites Pittsfield-Berkshires by IHG: Adventure awaits at the Holiday Inn & Suites Pittsfield-Berkshires, a family-friendly 3-star hotel located 17.7km from Windsor. Ideal for both leisure and business travelers, this property offers a plethora of adventure sports and recreational activities nearby, such as horseback riding, snowboarding, hiking, fishing, and cross-country skiing. The hotel is equipped with amenities tailored for children, including window guards and free cribs, ensuring a safe environment for families. Guests appreciate the blend of comfort, convenience, and exciting outdoor experiences that make this hotel a great choice for a memorable stay.
• Berkshire Mountain Lodge: Experience the charm of the Berkshire Mountain Lodge, a cozy 3-star lodge located 20.9km from Windsor. With a focus on golf-themed vacations, this family-friendly property provides guests with access to excellent golfing facilities. Whether you are a seasoned golfer or a beginner, you’ll find the perfect setting to enjoy the sport amidst the beautiful Berkshire region. The lodge offers a welcoming atmosphere for business travelers and families alike, making it an excellent choice for both relaxation and recreation.
• Club Wyndham Bentley Brook: Embrace the thrill of winter sports at Club Wyndham Bentley Brook, a 3-star hotel situated 20.9km from Windsor. Perfect for ski enthusiasts, this property offers easy access to ski shuttles and lifts, along with onsite snowboarding and downhill skiing opportunities. The surrounding area is rich with hiking and biking trails, making it an ideal destination for adventure seekers year-round. Guests enjoy modern accommodations that cater to their every need, ensuring a comfortable and exhilarating stay.

Where to stay near Windsor

Windsor, Massachusetts, offers an unforgettable vacation experience with its stunning outdoor adventures and family-friendly atmosphere. Explore the nearby scenic locations, including charming local wineries nestled in picturesque wine country. Whether you're seeking a romantic getaway or an adventurous escape, the region provides the perfect backdrop for relaxation and exploration. Don't miss the chance to enjoy the breathtaking scenery and cozy ambiance that Windsor and its surroundings have to offer.

• Pittsfield: Located 17.7km from Windsor, Pittsfield is a vibrant city that offers a wealth of outdoor adventures and cultural experiences. Known for its breathtaking landscapes, visitors flock here primarily in the summer months from June to August. Ski enthusiasts will appreciate the nearby ski resorts, while those seeking leisure can enjoy the picturesque lakes and mountains. Notable landmarks include serene parks and historical monuments, making it a perfect spot for both adventure-seekers and casual explorers.
• North Adams: Just 22.5km from Windsor, North Adams is an artistic hub with a rich cultural scene. With peak visitor arrivals during June to July and September, this city attracts those interested in adventure and art alike. Music concerts and cultural events are common here, alongside various ski activities during winter. The city is home to the renowned Mass MoCA (Massachusetts Museum of Contemporary Art), which features public art installations and vibrant cultural centers, providing a unique blend of creativity and outdoor fun.
• Savoy: A mere 6.4km from Windsor, Savoy is a quaint town known for its stunning scenery and outdoor experiences. Popular among nature lovers, it welcomes visitors year-round, with peak travel times in March to April and July. Savoy is ideal for skiing and enjoying the natural beauty of the nearby mountains and lakes. The area is dotted with picturesque waterfalls, offering an idyllic setting for hiking and relaxation, making it a perfect destination for those looking to connect with nature.

Things to do near Windsor

Windsor, Massachusetts, offers a perfect escape for outdoor enthusiasts and adventure seekers, especially those interested in skiing. Visitors can enjoy various activities, including skiing at local resorts and exploring ski fields. Additionally, for those looking to unwind, a wellness center is available to enhance your vacation experience. Whether you're hitting the slopes or relaxing, Windsor has something for everyone.

Shopping

In Windsor, you can enjoy shopping at local favorites. For a broader selection, if you're up for a drive, check out Guido's Marketplace and the North Adams shopping centers, all within 22.5km, offering a mix of city and family vibes perfect for gifts and souvenirs.

Recreation

Experience the serene outdoors at Bas Ridge Golf Course, just 9.7km from Windsor, where you can enjoy a round of golf amidst lush landscapes. Alternatively, relax at Windsor Lake Park, located 19.3km away, offering a peaceful retreat with wellness activities and nature trails.

Adventure

Experience thrilling adventures at Jiminy Peak Mountain Resort, a ski field located 20.9km from Windsor, offering exhilarating sports and ski vibes. For outdoor enthusiasts, Berkshire East Ski Resort, 19.3km away, provides skiing and adventure activities. Explore the Skyline Trail, a picturesque hiking trail, just 16.1km from Windsor.

Nightlife

Experience the enchanting nightlife in Windsor with a visit to the Colonial Theater, just 17.7km away, or the Adams Theater, 14.5km away, both offering captivating performances. For a unique cultural experience, don't miss the Barrington Stage Company, also 17.7km from Windsor, perfect for a memorable evening.

Booking tips and Expedia advantages for Windsor

To save money on your trip to Windsor, travel during the off-peak months of January or March to April when accommodation prices are lower. Tuesdays are the least expensive days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to find budget-friendly options and arrange your hotel, flights, and activities in a package deal for additional savings. Take advantage of free activities in the area and consider walking to explore Windsor, as it is compact and easy to navigate on foot.

• 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 options based on your budget, desired location, and preferred type of accommodation. For the best prices and offers, arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Windsor with your flights and activities through an Expedia package deal.

Find the best attractions near Windsor

Windsor, Massachusetts, is perfect for outdoor enthusiasts and adventure seekers, offering a variety of activities like skiing and exploring nature reserves. Visitors can immerse themselves in the stunning mountains and pristine landscapes, making it ideal for those looking for cultural experiences as well. With plenty of attractions catering to different interests, Windsor promises a memorable vacation filled with adventure and natural beauty.

• Mount Greylock: Experience the highest peak in Massachusetts, offering breathtaking views and a variety of outdoor activities. Whether hiking, biking, or simply enjoying the panoramic scenery, this mountain is perfect for adventure seekers and nature lovers alike.
• Wahconah Falls State Park: Just a short drive from Windsor, this park features stunning waterfalls and lush hiking trails. The tranquil environment is ideal for picnicking, birdwatching, and immersing yourself in the beauty of nature.
• Massachusetts Museum of Contemporary Art: Located nearby, this cultural hub showcases innovative art exhibits and installations. Explore the diverse collections and enjoy engaging events that highlight contemporary artists and their works.

Best time to go to Windsor

The best time to visit Windsor is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

Windsor, Massachusetts, is conveniently accessible from several major airports. Bradley International Airport (BDL) in Hartford, CT, is located 70.8km away, with great hotel options such as DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. Albany International Airport (ALB) is 67.6km away, with hotels like Park Manor Hotel and The Landing Hotel at Rivers Casino & Resort, both 12.9km from ALB. Lastly, Pittsfield Municipal Airport (PSF) is the closest, at 22.5km, offering nearby options like Hampton Terrace Inn, 8.0km away. Each hotel provides easy transportation access to their respective airports.