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Hotels in Middlebury

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Where to stay in Middlebury?

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 landmarks in Middlebury

Learn more about Middlebury

Middlebury is well-known for its attractions such as Quassy Amusement Park and Lake Quassapaug.

Either off access road at the end of Old Waterbury Rd, or Umberfield Rd. Abandoned in the woods near I 84 and power lines overhead.
Photo by Brandon Miller
Open Photo by Brandon Miller

Frequently asked questions

What hotels do travelers like in Middlebury?
Can I book refundable hotels in Middlebury?
If you need the flexibility to change your plans to Middlebury, most properties provide refundable* rates you can book. You can see these properties by searching our site and using the “fully refundable” filter to narrow down the results.
What will the weather in Middlebury be like during my vacation?
The warmest months in Middlebury are usually July and August with an average temp of 69°F. January and February are the chilliest months when the average temp is 32°F. The rainiest months are October and July.
Why should I book my Middlebury accommodation with Hotels.com?
There are plenty of reasons to book your Middlebury travel with us: our free cancellations on selected hotels* gives you the flexibility you’re looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Find out more about Middlebury

Find out more about Middlebury

Discover the Hidden Charms of Middlebury: Where Nature and Culture Embrace

Nestled in the heart of Connecticut, Middlebury is a charming blend of natural beauty and quaint New England charm. Known for its picturesque parks and scenic landscapes, this off-the-beaten-path destination invites travelers to explore the serene Woodbury Reservoir and the sprawling parks perfect for hiking and picnicking. Stroll through the charming streets lined with historic homes or indulge in local dining experiences. With a welcoming atmosphere and lush surroundings, Middlebury is an ideal retreat for nature lovers and those seeking a peaceful escape from the hustle and bustle of city life. For great hotel rates in Middlebury, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Middlebury

Middlebury, Connecticut offers a variety of hotel accommodations, ranging from cozy budget options to comfortable mid-range stays. You'll find welcoming inns and hotels with essential amenities, plus some upscale choices for a more luxurious experience. The nearby Waterbury area also features additional options, like the Hampton Inn. Here are some of the best hotels in Middlebury that our travelers love:

  1. DoubleTree by Hilton Hotel BristolOpens in a new window: This 4.0-star hotel offers a blend of comfort and convenience, featuring an onsite restaurant and bar, a delightful indoor pool, and a well-equipped fitness center. With top-notch amenities including a full-service restaurant, spa facilities, and proximity to local attractions, it caters perfectly to leisure travelers seeking a relaxing getaway. Review sentiments highlight the cleanliness, inviting atmosphere, and outstanding customer service, making it an ideal choice for those looking to enjoy a high-quality stay in a welcoming environment.
  2. Mayflower Inn & SpaOpens in a new window: This 4.0-star hotel is a haven for adventure seekers and luxury travelers. With a focus on unique experiences, it offers an array of outdoor activities such as hiking and mountain biking right at your doorstep. The property embraces a pet-friendly policy, enhancing the experience for those traveling with furry companions. Guests appreciate the beautifully designed spaces, making it an attractive destination for travelers who crave both adventure and comfort in a luxurious setting.
  3. The Litchfield InnOpens in a new window: This 4.0-star hotel is an exquisite choice for travelers seeking a spa retreat and luxurious amenities. With a full-service spa offering a variety of treatments and a serene ambiance, it is perfect for relaxation and rejuvenation. The beautifully appointed rooms and delicious breakfast options further enhance the experience, making it a top destination for leisure travelers. The property’s charming decor and excellent location provide a distinctive experience, ensuring a memorable stay surrounded by comfort and elegance.

Top locations to stay in Middlebury

When visiting Middlebury, Connecticut, consider staying in Monroe Center Historic District, Milldale, or Middlebury Center Historic District. Monroe Center offers charming churches and scenic waterfalls, while Milldale boasts outdoor adventures and vibrant nightlife. Middlebury Center is perfect for those interested in museums and nature. For first-time visitors, Monroe Center Historic District provides a delightful blend of history and natural beauty.

  1. Monroe Center Historic DistrictOpens in a new window: Monroe Center Historic District is a charming area known for its beautiful churches and stunning waterfalls, making it a peaceful retreat for travelers. The picturesque landscape invites visitors to explore its scenic spots, perfect for leisurely walks and photography. You can also enjoy relaxing at local beaches nearby, offering a great mix of nature and tranquility. This district is ideal for those looking to immerse themselves in a friendly community atmosphere while being close to various outdoor activities.
  2. MilldaleOpens in a new window: Milldale is an exciting place to stay, especially for those who love cultural attractions and outdoor adventures. With highlights like the scenic Mount Carmel and the breathtaking Sleeping Giant State Park, you can enjoy stunning views and ample opportunities for hiking and exploring nature. Milldale also offers a vibrant entertainment scene, including venues like the Palace Theatre and Toyota Oakdale Theatre, perfect for catching a show after a day of exploring. The area’s mix of shopping centers, like the Brass Mill Center, adds to its appeal, ensuring there's always something to do.
  3. Middlebury Center Historic DistrictOpens in a new window: Middlebury Center Historic District is a quaint area steeped in history and charm, showcasing beautiful museums and picturesque waterfalls. Ideal for those who appreciate a slower pace, this district offers a chance to explore local heritage and enjoy the natural beauty of the area. While it may be smaller than other destinations, the welcoming environment and unique attractions make it a delightful spot for a relaxing getaway, perfect for visitors who want to unwind and connect with the local culture.

Things to do in Middlebury

Nestled amidst rolling mountains and shimmering lakes, Middlebury beckons travelers with its stunning natural beauty. Explore lush forests, enjoy scenic hikes, or unwind by tranquil shores. This charming town offers a perfect blend of outdoor activities and cozy accommodations, making it an ideal spot for nature lovers and relaxation seekers alike.

  • Quassy Amusement ParkOpens in a new window – Dive into family-friendly fun at Quassy Amusement Park! With thrilling rides, games, and attractions, it's the ideal spot for a day filled with laughter and excitement. Don't miss the classic carousel and the chance to enjoy the beautiful surroundings.
  • Hop Brook LakeOpens in a new window – Take a break and unwind at Hop Brook Lake, where you can relish the tranquility of nature. Enjoy a peaceful day by the water, perfect for picnicking, fishing, or simply soaking in the serene landscape. It's a great escape for those looking to connect with nature.
  • Lake CompounceOpens in a new window – Get ready for an exhilarating day at Lake Compounce! As one of the oldest amusement parks in the country, it offers a mix of thrilling roller coasters and family-friendly rides. Splash around in the water park area for a refreshing retreat on warm days.
  • Union Station ClocktowerOpens in a new window – Step back in time at the Union Station Clocktower, a historic landmark that showcases stunning architecture. Snap some pictures and appreciate the craftsmanship that has stood the test of time, making it a lovely spot for history enthusiasts and casual visitors alike.
  • Whittemore Glen State ParkOpens in a new window – Explore the natural beauty of Whittemore Glen State Park, where you can hike scenic trails and take in breathtaking views. Perfect for outdoor lovers, this park invites you to enjoy a leisurely stroll or a more challenging hike in a tranquil setting.

5 tips for savvy savings when booking a hotel in Middlebury

  1. Book for the cheapest times: The most affordable time to visit Middlebury is between January and March, when hotel prices tend to be lower. For those looking to explore the town's historical landmarks and cultural attractions, a stay of at least 2 to 3 days is recommended. This duration allows visitors to discover key sites, including natural parks that showcase the area's rich history and culture. Traveling during this off-peak season not only offers great value for money but also makes it easier for budget-conscious travelers to enjoy all that Middlebury has to offer.
  2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Middlebury, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted rates on hotels as your travel date approaches. By enabling email alerts or push notifications, you could stay informed about flash sales and special promotions, helping you save on your stay. Additionally, use the Smart ShoppingOpens in a new window feature in the app to compare room rates and amenities, ensuring you’re aware of any price drops or availability changes. This way, you'll be well-equipped to seize opportunities for a budget-friendly getaway.
  3. Be flexible with dates: Prices can fluctuate based on several factors, including the hotel's location, star rating, and the time of year. Being flexible with your travel dates might help you find better rates for your stay in a Middlebury hotel. If you're in search of a distinctive experience, boutique hotels can provide a more personalized touch and potentially greater value. When you book through Hotels.com, we'll inform you whether the price for your chosen dates is above or below the average. If the price seems high, we’ll recommend more budget-friendly dates that could help you secure a better deal.
  4. Consider your location: Staying near major attractions or city centers can be convenient, but it usually tends to come with higher prices. For more affordable options, consider hotels in less central areas or neighborhoods, where you can find a balance between cost and easy access to the sights you want to see. You might also look into independent hotels a bit further out, which can offer a more genuine and budget-friendly experience.
  5. Join One Key™: Become a One Key MemberOpens in a new window for free and book your next stay in Middlebury. Save on over 100,000 hotels worldwide with exclusive member prices. As a member, you can quickly progress through the tiers and enjoy perks, like free room upgrades when available and food and beverage discounts at select VIP Access properties.

Best time to go to Middlebury

Middlebury experiences its lowest average temperature in January, at 28.0°F (-2.2°C), while July is the hottest month, with an average temperature of 73.2°F (22.9°C). October is usually the wettest month. April, May, and July are the peak travel months in Middlebury, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, October to December tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.

If you're looking to discover somewhere new, look no further than Middlebury. Whether you're planning to stay for a night or for the week, the area around Middlebury has accommodations to fit every need. Search for hotels in Middlebury with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Middlebury hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Middlebury hotel deals are here with our lowest price guarantee.