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Top Windsor hotels
Fat Sheep Farm & Cabins
The fat sheep farm is such a a cute cozy place. We partook in morning chores with Jay, she is absolutely amazing. She made everyone feel at home with interacting with the sheep. She was very knowledge and you can tell she genuinely loves the animals. Todd and Suzy are amazing as well. We breifly ...
Reviewed on Nov 10, 2025
Woodstock Inn & Resort
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town
Reviewed on Nov 26, 2025
Align Inn Vermont
The most beautiful scenic views!
Reviewed on Nov 30, 2025
The Mountain Inn at Killington
The front desk staff are patient and enthusiastic.
Reviewed on Nov 24, 2025
Hilton Garden Inn Hanover Lebanon
This hotel is solid. Location relative to Hanover is good, facility is nice, and it’s clean and comfortable. Would definitely stay again.
Reviewed on Nov 30, 2025
The Shire Woodstock
Clean good service and location
Reviewed on Nov 22, 2025
North Star Lodge and Resort
It was a great stay. Close to killington!
Reviewed on Nov 28, 2025
Killington Mountain Lodge, Tapestry Collection by Hilton
It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared.
Reviewed on Nov 30, 2025
White River Inn and Suites
Everything was satisfactory, no issues with the hotel. Very busy intersection just off the highway, driving is somewhat hectic.
Reviewed on Nov 27, 2025
Windsor Hotel & Travel Guide
Thinking about exploring Central Vermont- Killington? To experience it as the locals do, reserve places to base your trip that are within an easy drive from the excitement of Windsor. Travelocity's hotel guide presently has listed 5 accommodations in and around the CBD district and surrounds of Windsor.
The Holiday Inn Club Vacations Ascutney Mountain Resort is the nearest hotel to the downtown area of Windsor and it's simply a brief drive away.
13 miles (21 kilometers) from downtown Windsor, you will find the Castle Hill Resort And Spa. Alternatively, the Inn at Clearwater Pond can be found approximately 9 miles (15 kilometers) away. The Woodstock Inn & Resort along with the Mountain Lodge at Okemo Mountain Resort are some other Travelocity-listed accommodation options in Windsor.
Keen on discovering even more of the forests and mountains that this area features? What if you take some time in nearby places in Central Vermont? Take part in snowboarding, skiing and cross-country skiing or venture out to see the area's diverse cultural and scenic sights. Comfortable Travelocity-listed hotels are located nearby.
20 miles (32 kilometers) to the northwest of Windsor, you can find Killington, which is where you can visit Killington Ski Resort and Green Mountain National Golf Course. The Killington Grand Resort Hotel and Mountain Green Ski & Golf Resort are just a handful of the Travelocity hotel options in Killington. Or, you could stay in Rutland, 30 miles (45 kilometers) west of Windsor, where you can choose between the Hampton Inn Rutland and Holiday Inn Rutland-Killington Area. The Pine Hill Park and Vermont State Fairgrounds are a couple of the most popular sites to explore in Rutland.
Just because you are on a break, should not mean that you can't enjoy your love for a day at the stadium. Find Verizon Wireless Arena 60 miles (98 kilometers) to the southeast of Windsor. And travelers wishing to sleep close to the action can take their choice from the Hilton Garden Inn Manchester Downtown or the Radisson Hotel Manchester Downtown.
If you are traveling via Lebanon Municipal Airport and would like to stay nearby, try Hampton Inn White River Junction or Fireside Inn & Suites West Lebanon.
Top reasons for your vacation to Windsor
- Outdoor Adventures: Windsor, Vermont offers a range of outdoor activities including hiking, birdwatching, and sledding in winter.
- Historic Hamlet of West Windsor: Explore the charming historic hamlet of West Windsor and discover its rich history and architecture.
- 18th-Century Farmstead: Visit the 18th-century farmstead in Windsor and experience life on a traditional Vermont farm.
- Breathtaking Scenery: Take in the stunning scenery of Windsor with its beautiful countryside and mountain views.
- Recreation Opportunities: Enjoy the vast spaces for recreation in Windsor, perfect for outdoor games and family fun.
Find your favorite hotels in Windsor
If you're planning an adventure vacation in Windsor, Vermont, you'll find a variety of hotel accommodations to choose from. Whether you're looking for luxury hotels or budget-friendly options, there are plenty of choices available. Windsor offers a range of top hotels, providing comfortable and convenient stays for visitors. With a hotel map, you can easily find accommodations near the attractions and activities you're interested in exploring. From cozy inns to modern resorts, Windsor has something to suit every traveler's preferences.
| Hotel name | Type | Stars | Description |
| Windsor Mansion Inn | Bed & breakfast | 3.5 | This 3.5-star Bed & Breakfast is a great option for your Adventure vacation in Windsor, Vermont. With close proximity to snowshoeing, snowmobile riding, sledding, snowboarding, cross-country skiing, library, wedding, adventure, view, and hiking, it offers plenty of outdoor activities for you and your family to enjoy. The inn also provides comfortable accommodations and a charming atmosphere for a relaxing stay. |
| Fat Sheep Farm & Cabins | Agritourism property | 3.0 | If you're looking for a unique experience, this 3.0-star Agritourism property is the perfect choice. Located in Windsor, Vermont, it offers a rustic yet comfortable stay in a farm setting. You can enjoy farm activities and interact with animals, providing a memorable adventure for both kids and adults. |
| Snapdragon Inn | Bed & breakfast | 3.5 | This 3.5-star Bed & Breakfast is another excellent option for your Adventure vacation. With close proximity to segway tours, snowshoeing, rock climbing, sledding, snowboarding, cross-country skiing, historical sites, adventure, and hiking, it offers a range of exciting activities. The inn also boasts a charming ambiance and comfortable accommodations, ensuring a delightful stay. |
Explore the best activities and sights in Windsor
When visiting Windsor, Vermont, you'll find a wide range of exciting activities for an adventurous vacation with your family. With its close proximity to beer breweries, golf courses, forests, hiking trails, and mountains, there are plenty of outdoor activities to enjoy. You can go birdwatching and take in the beautiful scenery, or indulge in delicious chocolate treats. If you visit during winter, sledding is a popular activity. Windsor also offers a charming countryside setting, perfect for exploring and relaxing. Don't miss out on visiting local attractions like the Summit House and Bellows Falls, as well as discovering the literary greats associated with the area. Your adventure awaits in Windsor!
- Harpoon Brewery: Harpoon Brewery offers a captivating experience with its picturesque mountain views and scenic forests. Take a leisurely hike through the stunning countryside, immersing yourself in the beauty of nature. Enjoy a refreshing beer at the brewery while soaking in the serene atmosphere. For the adventurous, try your hand at golfing amidst the breathtaking landscapes. Birdwatching enthusiasts will be delighted by the diverse bird species that inhabit the area. Indulge in delectable chocolates and embrace the romance of this charming brewery. During the winter months, enjoy exhilarating sledding activities on the nearby slopes. Harpoon Brewery guarantees an entertaining and enchanting experience for all.
- Path of Life Garden: Path of Life Garden is a botanical oasis that offers a mesmerizing experience. Explore the enchanting river that runs through the garden, providing a tranquil backdrop for your visit. Embark on a delightful hike, immersing yourself in the beauty of the surrounding forests. Discover the vibrant flowers and plants that adorn this picturesque garden. Engage in friendly conversations with the welcoming locals and experience the warmth of a small town. For outdoor enthusiasts, indulge in a round of golf amidst the breathtaking mountain views. Immerse yourself in the captivating scenery and create unforgettable memories with your family. Path of Life Garden is a haven for nature lovers, offering a perfect blend of serenity and adventure.
- Brownsville Trail: Brownsville Trail is a paradise for outdoor enthusiasts. Embark on a thrilling hiking adventure, exploring the scenic trails that wind through the enchanting forests. Marvel at the majestic mountains that surround you, offering awe-inspiring views at every turn. Take part in guided tours to learn more about the rich history and culture of the area. Enjoy a round of golf amidst the breathtaking landscapes, perfecting your swing in this natural haven. Immerse yourself in the vibrant atmosphere of festivals that take place along the trail. Indulge in the scenic beauty that unfolds before your eyes and create unforgettable memories with your family. Brownsville Trail promises an exhilarating outdoor experience like no other.
Where to stay in Windsor
Windsor, Vermont is an ideal destination for an adventurous family vacation. With its proximity to beer, golf, forests, hiking, mountains, birdwatching, and breathtaking scenery, there are plenty of exciting activities to enjoy. Three must-try experiences include exploring the historic hamlet of West Windsor, visiting the 18th-century farmstead, and taking advantage of the vast spaces for recreation. Whether you're seeking a taste of history, outdoor adventures, or simply want to relax in the beautiful countryside, Windsor has something for everyone. Get ready for an unforgettable adventure vacation in this charming Vermont town!
- Ascutney: Ascutney is a charming city nestled in the mountains of Vermont. Its small-town atmosphere and friendly people make it a perfect destination for a family adventure vacation. With its budget-friendly accommodations and ski opportunities, Ascutney offers a unique experience for outdoor enthusiasts. Families can enjoy skiing or snowboarding on the slopes of Mount Ascutney or explore the scenic hiking trails in the surrounding area. The picturesque mountain views and tranquil atmosphere provide a peaceful getaway from the hustle and bustle of city life. Whether you're looking for a thrilling ski adventure or a relaxing nature retreat, Ascutney has something to offer for everyone.
The travel seasons of Windsor
Trips to Windsor show no change in popularity throughout the year. The peak season to visit is from July to September, with July being the highest month. Off-peak season starts from December to February, and December sees the least travelers.
Windsor has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 65.8 degrees Fahrenheit. The wettest month in Windsor is July, so pack accordingly.
 Calendar Month |  Temperature |  Precipitation |  Cloudiness |
| January | 16.7°F (-8.5°C) | Light Rain | Mostly Cloudy |
| February | 18.9°F (-7.3°C) | Light Rain | Mostly Cloudy |
| March | 27.1°F (-2.7°C) | Light Rain | Mostly Cloudy |
| April | 39.4°F (4.1°C) | Light Rain | Mostly Cloudy |
| May | 52.3°F (11.3°C) | Light Rain | Mostly Sunny |
| June | 59.9°F (15.5°C) | Light Rain | Mostly Sunny |
| July | 65.8°F (18.8°C) | Light Rain | Mostly Sunny |
| August | 64.0°F (17.8°C) | Light Rain | Mostly Sunny |
| September | 57.0°F (13.9°C) | Light Rain | Mostly Sunny |
| October | 45.5°F (7.5°C) | Light Rain | Mostly Cloudy |
| November | 33.1°F (0.6°C) | Light Rain | Mostly Sunny |
| December | 24.3°F (-4.3°C) | Light Rain | Mostly Cloudy |
Food and dining in Windsor
When visiting Windsor, Vermont, you will find a variety of local cuisines to satisfy your food cravings. One popular restaurant in the neighborhood is Pizza Chef, a highly rated pizzeria that offers delicious pizzas and other Italian dishes. If you're looking for a restaurant in a hotel, Windsor Station Rest is a great option known for its tasty meals and cozy atmosphere. For those on a budget, there are several inexpensive restaurants in Windsor where you can enjoy a satisfying meal. Many of these restaurants feature locally sourced ingredients, ensuring a fresh and flavorful dining experience.
How do I find a great hotel with Travelocity?
Make sure your entire crew enjoys an unforgettable vacation. When looking for the ideal accommodations, utilize our family-friendly badge to find hotels that offer additional amenities for children. Moreover, our personalized filters assist you in narrowing down hotels that are conveniently located near popular attractions, provide enhanced cleaning, and fit within your budget.
Why should I book with Travelocity?
Conference calls, to-do lists, and, of course, football practice. Busy lives and packed schedules require hassle-free trips. Our aim is to provide worry-free travel every time you and your family book with us, allowing you to spend less time fretting and more time creating cherished memories. With our assistance, you can discover and plan your ideal trip, benefit from transparent pricing and trustworthy reviews, and receive 24/7 guaranteed customer support before, during, and after your vacation.
How can I save money on my trip to Windsor?
Avoid the peak season from July to September when planning your trip to Windsor, Vermont. This will help you save money on accommodations and attractions. Consider bundling your flights, hotel, and car bookings to get a discounted price. In terms of inexpensive local activities, Windsor offers opportunities for hiking in its scenic forests, exploring the countryside, and enjoying sledding during the winter months. These activities provide a budget-friendly way to experience the natural beauty of Windsor.
Frequently asked questions
Recent Windsor hotel reviews by fellow wanderers
Killington Mountain Lodge, Tapestry Collection by Hilton
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