Middlebury, CT

Travel Guide

A weathered stone structure with steps and a small opening, surrounded by fallen leaves and moss.

Where to stay in Middlebury

Find the best Middlebury areas and neighborhoods for the activities you enjoy most. Learn more about Middlebury
Learn more about Middlebury

Middlebury Center Historic District

Visitors to Middlebury Center Historic District enjoy its historic sites, and if you want to do some exploring, Lake Quassapaug is worth a stop.

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
$139 nightly
The price is $160 total per night from Nov 5 to Nov 6
$160 total
Nov 5 - Nov 6
Total with taxes and fees
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (2,392 reviews)
"Excellent location’ large room and comfortable bed. Convenient if pricey parking across the street. But TV only worked with a chrome cast app we don’t have and “bar” offerings were expensive and undrinkable."

Reviewed on Oct 14, 2026

New Haven Hotel
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
$152 nightly
The price is $175 total per night from Oct 25 to Oct 26
$175 total
Oct 25 - Oct 26
Total with taxes and fees
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Trumbull Marriott Shelton
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
$110 nightly
The price is $126 total per night from Oct 18 to Oct 19
$126 total
Oct 18 - Oct 19
Total with taxes and fees
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,870 reviews)
"The queen size bed was extremely squeaky and lacked support in that laying on it caused the bed to uncomfortably sink. By the third night my sleep was totally unrestful. I witnessed a cockroach (medium-sized) crawling on the counter alongside the toaster as I was toasting a bagel during breakfast. ..."

Reviewed on Oct 14, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,073 properties 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.
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
240 Congress Avenue New Haven CT
Stay at this aparthotel in New Haven. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Shubert Theater and Schubert Performing Arts ...
9.6/10 Exceptional! (90 reviews)
"Overall, we really enjoyed our stay. The property was just as advertised—spacious, clean, modern, and comfortable, with a nice view of New Haven and a great location convenient to shops and the Yale campus. The apartment was thoughtfully stocked with toiletries, kitchen essentials, linens, and plenty ..."

Reviewed on Oct 6, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
9 Tower Ln New Haven CT
Book a stay at this business-friendly aparthotel in New Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Knights of Columbus Museum ...
9.2/10 Wonderful! (35 reviews)
"Fast and effective check-in, great amenities in the building. Kitchen well furnished. Overall great experience."

Reviewed on Oct 11, 2026

Hyatus Luxury Residences City Crossing
Cozy cottage with AC and lake access in charming Connecticut suburb.

Cozy cottage with AC and lake access in charming Connecticut suburb.

Watertown CT
Stay at this cottage in Watertown. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Lake Winnemaug and Lake Quassapaug are located ...
9.6/10 Exceptional! (18 reviews)
"We had a wonderful stay at this cozy little cottage! The space was very clean, comfortable, and well cared for. It was such a peaceful and relaxing place to stay, and we really enjoyed the quiet atmosphere. The cottage had everything we needed and was the perfect little getaway. We would definitely ..."

Reviewed on Oct 5, 2026

Cozy cottage with AC and lake access in charming Connecticut suburb.
See all properties 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.

Stay near popular Middlebury attractions

Quassy Amusement Park

8.2/10 (21 reviews)
Bring the kiddos to Quassy Amusement Park and have a fun-filled day at this theme park in Middlebury. Attend a sporting event in this family-friendly area.
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Frequently asked questions

Is Middlebury worth visiting?
Middlebury is worth visiting for its family-friendly attractions, including Quassy Amusement Park. Travelers can also enjoy diverse dining experiences, with Italian and North American cuisine available. You'll find options ranging from classic pasta dishes to comforting American fare.
When is the best time to visit Middlebury?
The best time to visit Middlebury is from May through July, when the destination is most popular. For fewer crowds and better value, the quieter months of October through December are a good bet, offering a different experience with fewer travelers.
What is Middlebury known for?
Middlebury is known for Quassy Amusement Park, a popular destination that offers fun and entertainment for travelers. The area also boasts a strong Italian food culture, providing diverse and delicious dining experiences.
What is a good itinerary length for Middlebury?
A good itinerary length for Middlebury is one day to enjoy Quassy Amusement Park. For a more relaxed visit or an extended stay of two days, travelers can take their time at the park and explore the local dining scene, which offers Italian, North American, and Asian cuisines.
What are the top things to do in and around Middlebury?
In Middlebury, travelers can visit Quassy Amusement Park, a popular attraction in the area.
What cuisines can you find in Middlebury?
In Middlebury you can find Italian cuisine, offering classic dishes like pasta, pizza, and lasagna. Beyond that, travelers can also enjoy North American favorites, Chinese dishes, and Latin American options, including Mexican food. The area also has coffee shops and pubs.
Can I book a refundable hotel in Middlebury?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Middlebury by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Middlebury with Expedia?
Expedia makes it easier to plan your Middlebury trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Middlebury?
The best choice depends on your travel style. Hotels in Middlebury can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Middlebury trip on Expedia?
Once you've booked your Middlebury trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Middlebury trip?
Expedia offers customer support before, during, and after your Middlebury trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Middlebury?
If it's your first trip to Middlebury, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Middlebury hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Middlebury hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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