Windsor Hotels

Top reasons to visit Windsor

• Outdoor Adventures: Windsor is a haven for outdoor enthusiasts, offering skiing, hiking, and picturesque nature reserves.
• Relaxation and Wellness: Unwind at the local wellness centre after an exhilarating day of activities.
• Scenic Beauty: Enjoy breathtaking landscapes that provide a serene atmosphere for all visitors.
• Charming Neighbourhoods: Explore nearby towns filled with character, perfect for a leisurely stroll or shopping.
• Local Wineries: Discover delightful wineries in the surrounding wine country, ideal for romantic getaways.

Find great hotels near Windsor

Discover a delightful range of accommodation options in Windsor, Massachusetts, ideal for families, couples, and ski enthusiasts alike. From charming motels to luxurious resorts, the area's hotels offer essential amenities and services tailored to enhance your stay. Whether you're seeking the best hotels or reading reviews, you'll find the perfect base to explore the scenic beauty of Windsor and enjoy a memorable vacation experience.

• FairBridge Inn Express: Ideal for business travellers, FairBridge Inn Express offers a straightforward and efficient stay, located a mere 12.9km from Windsor. This motel-style accommodation focuses on providing essential amenities with a professional touch. Guests appreciate the comfortable rooms designed for productivity, complimentary Wi-Fi, and business centre services that cater to the needs of the modern traveller. The property strikes a balance between convenience and comfort, making it a reliable choice for those visiting on work-related trips.
• The Central Downtown Inn & Suites: This charming 4-star guesthouse, situated 19.3km from Windsor, is perfect for pet lovers looking for a welcoming stay. The Central Downtown Inn & Suites allows pets on-site, ensuring that your furry companions can enjoy the vacation too. With amenities such as designated pet areas and a flexible pet policy, guests can relax knowing their pets are accommodated. The property also boasts elegantly designed rooms and a central location, making it easy to explore the local attractions while enjoying a comfortable retreat.
• Blue Vista Motor Lodge: Set in a picturesque location 19.3km from Windsor, Blue Vista Motor Lodge is a nature-themed motel that captivates guests with its serene surroundings. Ideal for those seeking an outdoor adventure, this accommodation provides easy access to hiking trails and scenic landscapes. The lodge features comfortable rooms with rustic decor, inviting guests to unwind after a day of exploration. Visitors often commend the tranquil atmosphere and the friendly staff, making it a fantastic choice for nature enthusiasts looking to reconnect with the great outdoors.

Where to stay near Windsor

Windsor, Massachusetts, is a delightful escape for those seeking outdoor adventures and scenic beauty. Explore local wineries in the surrounding wine country, perfect for a romantic getaway or family-friendly outings. The area's picturesque landscapes offer a serene atmosphere, while nearby towns invite you to discover charming neighbourhoods filled with character. Whether you’re skiing down snow-capped mountains or enjoying the tranquil surroundings, Windsor promises an unforgettable experience for every traveller.

• Pittsfield: Located 17.7km from Windsor, Pittsfield is a vibrant city that serves as a gateway to outdoor adventures. With a steady influx of visitors year-round, the peak season occurs from June to August, when adventurers flock to its renowned ski resorts and outdoor venues. Nature lovers will appreciate the stunning local landmarks, including picturesque lakes and majestic mountains. Whether you're hitting the slopes or enjoying a relaxing day by the water, Pittsfield offers a diverse range of activities that cater to all interests.
• North Adams: Just 22.5km away from Windsor, North Adams boasts a rich cultural scene alongside its thrilling outdoor experiences. The city attracts visitors primarily from June to July and September, with events like music concerts and cultural exhibitions drawing crowds. Explore the renowned art museum and captivating public art installations that reflect the city's artistic spirit. Outdoor enthusiasts can also partake in skiing and other adventures, making North Adams a perfect blend of culture and recreation.
• Savoy: A mere 6.4km from Windsor, Savoy is a hidden gem for those seeking scenic beauty and outdoor escapades. With visitor numbers peaking in March to April and July, it is an ideal spot for adventure seekers and nature lovers alike. The area is home to stunning lakes, breathtaking mountains, and enchanting waterfalls, offering excellent opportunities for hiking and skiing. Savoy’s tranquil atmosphere and natural splendour provide a perfect backdrop for relaxation and exploration.

Things to do near Windsor

Windsor, Massachusetts, is ideal for outdoor enthusiasts seeking adventure and winter sports. You can enjoy skiing at the local ski resort and explore the picturesque ski fields. For relaxation, don’t miss the wellness centre, perfect for unwinding after a day of activities. Whether you’re hitting the slopes or indulging in some self-care, Windsor offers a delightful mix of outdoor fun and rejuvenation.

Shopping

In Windsor, you can enjoy local shopping experiences, but if you're up for a drive, the North Adams Centre and Guido's Marketplace, both 20.9km away, offer a variety of shops. The North Adams Gateway Centre, 22.5km from Windsor, also provides a vibrant shopping atmosphere for families and businesses.

Recreation

Bas Ridge Golf Course, located 9.7km from Windsor, offers a vibrant outdoor atmosphere ideal for sports enthusiasts. Skyline Country Club, 16.1km away, provides a similar experience with its scenic golf facilities. For relaxation, Windsor Lake Park, 19.3km distant, is perfect for unwinding amidst nature’s beauty.

Adventure

Experience the thrill of skiing at Jiminy Peak Mountain Resort, a fantastic ski field located 20.9km from Windsor, offering exhilarating slopes and vibrant sports atmosphere. Alternatively, explore the Berkshire East Ski Resort for more outdoor adventures, or hike the Skyline Trail, renowned for its stunning scenery just 16.1km away.

Nightlife

Experience the charm of the Adams Theater, just 14.5km away, for a night of romance and culture. Alternatively, enjoy the thrill of the Thunderbolt Mountain Coaster, 19.3km from Windsor, or catch a show at the Colonial Theater, 17.7km away, for an unforgettable evening.

Booking tips and Expedia advantages for Windsor

To save money on your trip to Windsor, Massachusetts, consider visiting during the cheaper months of January and March to April, with Tuesdays being the most affordable days for accommodation. Use Expedia’s search tool to compare room rates, find eco-certified hotels, and combine bookings for better deals on flights and activities. Additionally, explore free local attractions and utilise public transport options to further minimise costs. Avoid peak times like July, August, and Saturdays to secure great savings on your stay.

• 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 enables you to specify your budget, preferred destination, and additional criteria. You can sort the results to display the lowest prices first, allowing you to find the most affordable accommodation options right away. Furthermore, you can refine your search by hotel type; 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.

Find the best attractions near Windsor

Windsor, Massachusetts, offers an ideal setting for outdoor enthusiasts and adventure seekers, featuring stunning nature reserves and mountains. Visitors can explore a variety of attractions that highlight the area's natural beauty and cultural experiences, making it perfect for those seeking an adventurous holiday. Whether you're skiing or hiking, Windsor provides numerous opportunities to immerse yourself in the great outdoors.

• Hail to the Sunrise Statue: A striking monument located 17.7km from Windsor, Hail to the Sunrise Statue radiates cultural significance. This iconic statue embodies the spirit of the local community and offers a serene spot for reflection amidst its picturesque surroundings.
• Charlemont Historical Society and Museum: Situated 19.3km away, this museum is a treasure trove of historical artefacts and exhibits that celebrate the rich heritage of the area. Visitors can immerse themselves in local history and culture through engaging displays.
• Mount Greylock: Located 17.7km from Windsor, Mount Greylock is the highest peak in Massachusetts, offering breathtaking scenery and outdoor adventures. Hikers can explore myriad trails and enjoy stunning panoramic views from the summit.

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 (BDL-Bradley Intl.) is located 70.8km away, with nearby hotels such as the 4-star Simsbury 1820 House, 11.3km from the airport, and the 3.5-star Marriott Hartford/Windsor Airport, just 6.4km away. Albany, NY (ALB-Albany Intl.) is 67.6km from Windsor, featuring hotels like The Landing Hotel at Rivers Casino & Resort and Crowne Plaza Albany, both 12.9km from the airport. Lastly, Pittsfield, MA (PSF-Pittsfield Municipal) is only 16.4km away, with options including the 4-star Seven Hills Inn, 9.7km from the airport, providing convenient access to your destination.