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Top Windsor hotels

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top hotels in Windsor for Extended Stay

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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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.

Windsor hotels essential information

Accommodation
2,460 hotels
Lowest Price
$116
Highest Price
$373
Popular hotels
Killington Mountain Lodge, Tapestry Collection by Hilton, Hampton Inn White River Junction, Woodstock Inn & Resort, Hotel Coolidge, Align Inn Vermont, White River Inn and Suites, The Mountain Inn at Killington, North Star Lodge and Resort, Hilton Garden Inn Hanover 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 nameTypeStarsDescription
Windsor Mansion InnBed & breakfast3.5This 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 & CabinsAgritourism property3.0If 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 InnBed & breakfast3.5This 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!

  1. 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.
  2. 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.
  3. 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!

  1. 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.

Best times to go to Windsor

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January16.7°F (-8.5°C)Light RainMostly Cloudy
February18.9°F (-7.3°C)Light RainMostly Cloudy
March27.1°F (-2.7°C)Light RainMostly Cloudy
April39.4°F (4.1°C)Light RainMostly Cloudy
May52.3°F (11.3°C)Light RainMostly Sunny
June59.9°F (15.5°C)Light RainMostly Sunny
July65.8°F (18.8°C)Light RainMostly Sunny
August64.0°F (17.8°C)Light RainMostly Sunny
September57.0°F (13.9°C)Light RainMostly Sunny
October45.5°F (7.5°C)Light RainMostly Cloudy
November33.1°F (0.6°C)Light RainMostly Sunny
December24.3°F (-4.3°C)Light RainMostly 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

What are the top kid-friendly hotels in Windsor?
From carefully considered amenities to extra room, kid-friendly hotels come with features that can help turn a good family vacation into a fabulous one. These Windsor properties make vacationing with the youngsters a breeze: The whole team will love staying at Snapdragon Inn. Complimentary breakfast and a picnic area are just a couple of the things that help make this place a sought-after option. Also consider Windsor Mansion Inn. It offers a trampoline, complimentary breakfast and ample opportunities for family time.
Where can I find cheap hotels in Windsor?
At Travelocity you’ll find really nice hotels in Windsor at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Windsor rather than in Windsor. We may find you even better rates, too.
How do I find the best Windsor hotel deals?
Simple! On Travelocity, look through the fantastic offers we’ve already found in Windsor then use our filters to find a great deal that’s perfect for you. Enter your travel dates, select the number of rooms you need, and we’ll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Windsor?
The cheapest hotel in Windsor is $116. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel’s location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Windsor?
There are 2,460 hotels in Windsor on Travelocity.
What are the best hotels in Windsor?
Windsor has so many great hotels to choose from at Travelocity — and it’s so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Windsor for you!
When is the best time to visit Windsor?
If you want the joy of a fun-filled trip in peak season, visit Windsor during January, August and November. If you’d prefer the peace of off-season, book a stay during quieter months, such as April, May and October.
When is the cheapest time to stay in Windsor?
Based on historic data is usually the cheapest month to visit Windsor. However, we have incredible deals all year round, so we’re confident you’ll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Windsor?
There are multiple hotels in Windsor that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We’ve got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Windsor. We have plenty of kid-friendly hotels in Windsor to choose from on Travelocity!
Why book a hotel in Windsor through Travelocity?
Because we have the top hotels in Windsor! We want to help you travel more and worry less. That’s why we’ve put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you’re getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Windsor on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Windsor hotel reviews by fellow wanderers