Hotels in Middlebury

Some of the best places to stay in Middlebury are Downtown New Haven and Barry Square. Downtown New Haven is vibrant, with a mix of culture, dining, and entertainment, making it ideal for first-time visitors. Barry Square offers a more suburban feel and is great for relaxation. In both areas, you’ll find a range of accommodations, from boutique hotels to familiar chains, ensuring comfort for different budgets. For a memorable stay, consider options in nearby towns like Southbury and Waterbury, which provide easy access to attractions while offering additional hotel choices. These are some of the hotels preferred by our travelers in Middlebury:

1. Downtown New HavenOpens in a new window: Experience the rich cultural heritage of Downtown New Haven, home to prestigious educational institutions like Yale University and the University of New Haven. This area is vibrant with art, music, and culinary delights, making it a perfect base for exploring the city. For a comfortable stay, consider Omni New Haven Hotel at YaleOpens in a new window, a 4.0-star hotel ideal for business, family, and pet travelers, offering meeting rooms and amenities for children. Another option is Graduate by Hilton New HavenOpens in a new window, a 4.0-star pet-friendly hotel that welcomes dogs and cats. If you're traveling with a pet and need business facilities, The Blake HotelOpens in a new window is another excellent choice, featuring meeting rooms and pet amenities.
2. Barry SquareOpens in a new window: Barry Square is a lively area characterized by its sports venues and cultural attractions, including the XL Center and the Connecticut Convention Center. It's an ideal location for both business and leisure travelers. For a luxurious experience, Rock Hall Luxe LodgingOpens in a new window is a 4.5-star Bed & Breakfast that caters to business travelers with meeting facilities. Alternatively, Marriott Hartford DowntownOpens in a new window is a 4.0-star hotel offering spa services and comprehensive business amenities, perfect for unwinding after a long day. For those traveling with pets, Simsbury 1820 HouseOpens in a new window provides comfortable accommodations along with pet-friendly policies and business services.

Three days in Middlebury offer a delightful escape into stunning natural landscapes, featuring serene lakes, rolling hills, and lush forests. Visitors can enjoy hiking, kayaking, or simply relaxing by the water, making it an ideal destination for nature lovers seeking tranquility and adventure. Here's a quick itinerary to make the most of your trip to Middlebury:

• Day 1: Begin your adventure in Middlebury by spending the morning at Lake Quassapaug, a picturesque spot perfect for outdoor activities such as kayaking or picnicking. After enjoying the serene waters, head over to the Apothecary Building, where you can explore the rich history of local pharmacy practices and admire its charming architecture. As the day winds down, make your way to the Union Station Clocktower, an iconic landmark that offers a glimpse into the town's historical significance. The clocktower is a great place to snap some photos and reflect on your day.
• Day 2: Start your day at Lake Compounce, Connecticut's largest amusement park, where thrilling rides and family fun await. After an exciting morning, visit the New Life Christian Church for a peaceful moment of reflection. Finally, make your way to the Carrie Welton Fountain, a beautiful site to relax and enjoy the surrounding greenery while soaking in the local atmosphere.
• Day 3: Your journey continues at Hop Brook Lake, an ideal location for hiking and enjoying nature's beauty. Next, visit the Glebe House Museum and The Gertrude Jekyll Garden, which offers a delightful experience of history, art, and stunning landscapes. Afterward, head to Southford Falls State Park for a breathtaking view of cascading waterfalls and serene trails, perfect for a leisurely stroll to wrap up your Middlebury experience.

1. Book for the cheapest times: The most budget-friendly time to visit Middlebury is during January, February, and December, when hotel rates are more affordable. To truly experience the area's highlights, it's recommended to stay for at least 2-3 days. While you're there, you can enjoy the beautiful natural parks that add great value to your trip.
2. Look for last-minute deals on Hotels.com: If you're looking for last-minute deals to Middlebury, Hotels.com offers an excellent way to score great discounts on hotel stays. To explore these offers, head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on Hotels.com, where you're more likely to find reduced rates as your travel date approaches. You could also sign up for email alerts or push notifications, keeping you informed about flash sales and special last-minute promotions, so you don’t miss out on an opportunity to save.
3. Be flexible with dates: Prices can fluctuate depending on factors like the hotel's location, star rating, and the time of year. As a result, being flexible with your travel dates could help you find lower hotel rates in Middlebury.
4. Consider your location: When booking on Hotels.com for your holiday, keep your location in mind. Staying closer to major attractions or downtown areas can offer convenience, but it usually tends to be more expensive. For more affordable options, consider hotels in neighborhoods that are less central, while still weighing the cost against the ease of getting to the sites you want to visit.
5. Upgrade with One Key: Make your next booking in Middlebury and sign up to Hotels.com's free One Key program, letting you earn and use reward points on your next stay. Progress through the Blue, Silver, Gold and Platinum tiers to unlock various advantages like room upgrades when available, discounted rates, and exclusive offers for members. Don't hesitate, sign up today.

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 tends to be the wettest month. The peak travel months to visit Middlebury are April, May, and July, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, October to December are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny conditions.