A multi-tiered waterfall cascading over dark rocks surrounded by lush greenery.

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Our top choices for Middlebury hotels

1. Wyndham Southbury

Wyndham Southbury
3.0 star property
Southbury
8.2 out of 10, Very good, (1,336 reviews)
"Breakfast cost extra. Room was very spacious. Pool was nice."
United States
Brooklyn
6 days ago
$87 nightly
The price is $100
Dec 8 - Dec 9
Total with taxes and fees
Wyndham Southbury

2. Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
3.0 star property
Waterbury
8.6 out of 10, Excellent, (1,296 reviews)
"I would definitely stay there again."
United States
Ludim
5 days ago
$89 nightly
The price is $102
Nov 9 - Nov 10
Total with taxes and fees
Courtyard by Marriott Waterbury Downtown

3. New Haven Hotel

New Haven Hotel
3.5 star property
Downtown New Haven
9.2 out of 10, Wonderful, (2,409 reviews)
"Bonus for the incredibly wonderful people."
United States
Elizabeth
4 days ago
$130 nightly
The price is $150
Nov 27 - Nov 28
Total with taxes and fees
New Haven Hotel

4. Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center
3.5 star property
Southbury
8.4 out of 10, Very good, (1,004 reviews)
"A great place for a one night stop."
United States
Louise
15 days ago
$130 nightly
The price is $149
Nov 12 - Nov 13
Total with taxes and fees
Heritage Hotel, Golf & Conference Center

5. Ethan Allen Hotel

Ethan Allen Hotel
3.5 star property
Danbury
8.0 out of 10, Very good, (1,551 reviews)
"Love staying here and would love for them to upgrade the WIFI."
United States
Teesha
1 day ago
$91 nightly
The price is $105
Dec 6 - Dec 7
Total with taxes and fees
Ethan Allen Hotel

6. Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale
4.0 star property
Downtown New Haven
8.8 out of 10, Excellent, (1,122 reviews)
"Everything was great from staff to food to rooms."
United States
anila
1 day ago
$161 nightly
The price is $185
Nov 22 - Nov 23
Total with taxes and fees
Omni New Haven Hotel at Yale

7. Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven
2.5 star property
West Haven
8.2 out of 10, Very good, (1,902 reviews)
"Self parking was great staff was very helpful. Rooms were very clean."
United States
Mona
2 days ago
$110 nightly
The price is $126
Nov 18 - Nov 19
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven

8. Hampton Inn Waterbury

Hampton Inn Waterbury
2.5 star property
Waterbury
8.0 out of 10, Very good, (1,001 reviews)
"People nice Breakfast good The room."
United States
Andrew
9 days ago
$105 nightly
The price is $121
Nov 15 - Nov 16
Total with taxes and fees
Hampton Inn Waterbury

9. The Capitol Hotel

The Capitol Hotel
3.0 star property
Downtown Hartford
7.2 out of 10, Good, (1,623 reviews)
"Staff were pleasant, breakfast was good."
United States
Heather
1 day ago
$90 nightly
The price is $104
Dec 9 - Dec 10
Total with taxes and fees
The Capitol Hotel

10. The Circle Hotel Fairfield

The Circle Hotel Fairfield
3.0 star property
Grasmere
8.8 out of 10, Excellent, (1,487 reviews)
"Breakfast was really nice. Very comfortable stay."
United States
alan
20 days ago
$152 nightly
The price is $175
Dec 6 - Dec 7
Total with taxes and fees
The Circle Hotel Fairfield

11. Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection
5.0 star property
Washington
9.4 out of 10, Exceptional, (67 reviews)
"Everything was perfect the room, the service, the restaurant, the spa; everything was perfect."
United States
Moshe
September 13th, 2026
$768 nightly
The price is $883
Nov 9 - Nov 10
Total with taxes and fees
Mayflower Inn & Spa, Auberge Collection

12. La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven
3.0 star property
Long Wharf
6.0 out of 10, (1,360 reviews)
"Parking was convenient and the complimentary breakfast was a great treat."
United States
Kenneth
September 28th, 2026
$113 nightly
The price is $130
Dec 2 - Dec 3
Total with taxes and fees
La Quinta Inn & Suites by Wyndham New Haven

13. Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
2.5 star property
Southington
8.6 out of 10, Excellent, (1,469 reviews)
"Breakfast was adequate. Everything tasted fine. Hotel staff were efficient."
United States
Alicia
2 days ago
$92 nightly
The price is $106
Nov 19 - Nov 20
Total with taxes and fees
Holiday Inn Express Southington by IHG

14. Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven
3.0 star property
Milford
8.6 out of 10, Excellent, (1,413 reviews)
"Staff are professional. Really made my work stay enjoyable."
United States
Rocco
11 days ago
$107 nightly
The price is $123
Nov 21 - Nov 22
Total with taxes and fees
Hyatt Place Milford / New Haven

15. Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton
4.0 star property
Long Wharf
9.4 out of 10, Exceptional, (1,014 reviews)
"Clean room bathroom was clean. No problems only stay one night."
United States
Patrick
2 days ago
$123 nightly
The price is $142
Dec 6 - Dec 7
Total with taxes and fees
Hotel Marcel New Haven, Tapestry Collection By Hilton

16. Trumbull Marriott Shelton

Trumbull Marriott Shelton
3.5 star property
Trumbull
7.8 out of 10, Good, (1,001 reviews)
"Perfect stay. Ordered dinner one night from the restaurant. The rooms are huge."
United States
Kelly
8 days ago
$127 nightly
The price is $146
Nov 22 - Nov 23
Total with taxes and fees
Trumbull Marriott Shelton

17. Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area
3.0 star property
West River
9.0 out of 10, Wonderful, (1,154 reviews)
"The staff was very helpful. Breakfast was delicious."
United States
Abigail
5 days ago
$117 nightly
The price is $134
Nov 29 - Nov 30
Total with taxes and fees
Cambria Hotel New Haven University Area

18. The Watershed

The Watershed
3.5 star property
Cranbury
9.2 out of 10, Wonderful, (1,005 reviews)
"Bed was fabulous. Staff is y friendly. The complimentary breakfast was outstanding."
United States
Debbie
6 days ago
$159 nightly
The price is $183
Dec 6 - Dec 7
Total with taxes and fees
The Watershed

19. Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven
3.0 star property
Orange
9.2 out of 10, Wonderful, (1,004 reviews)
"Great place to stay. I really enjoyed my stay again from beginning to end."
United States
Mark
25 days ago
$119 nightly
The price is $137
Dec 6 - Dec 7
Total with taxes and fees
Homewood Suites by Hilton Orange New Haven

20. The Milestone Inn

The Milestone Inn
2.5 star property
Woodbury
8.8 out of 10, Excellent, (216 reviews)
"Convenient, quiet location. Room was clean."
United States
Jill
1 day ago
$119 nightly
The price is $137
Nov 9 - Nov 10
Total with taxes and fees
The Milestone Inn
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Where to stay in and around Middlebury

Middlebury offers a delightful blend of outdoor adventures and family-friendly activities. Explore the scenic Heritage Road and Heritage Trail, or take in the stunning views near Mount Hood. Don't miss the vibrant acres of wildflowers that make this area a picturesque getaway for relaxation and romance.

Waterbury

Discover Waterbury, a vibrant city perfect for family travelers seeking a blend of outdoor adventures and urban experiences. With attractions like the thrilling Lake Compounce amusement park and the historic Quinnipiac University, there's plenty to explore. Waterbury is also home to the impressive City Hall and various educational venues, making it an engaging destination year-round. Located about 5 miles by car from Middlebury, Waterbury is an excellent choice for your stay, offering a unique mix of activities for everyone.

Southington

Experience the charm of Southington, an excellent hub for families and adventure-seekers who want a mix of excitement and relaxation. This vibrant city features attractions like Lake Compounce amusement park and Quinnipiac University, perfect for creating lasting memories. With a variety of outdoor activities and educational venues, Southington offers something for everyone. Located about 15 miles by car from Middlebury, it's a smart choice for your stay, balancing convenience with delightful experiences.

Naugatuck

If you are a traveler seeking a blend of outdoor adventure and family-friendly activities, look no further than Naugatuck, Connecticut. This vibrant city offers easy access to attractions like Yale University, where you can immerse yourself in history, and the scenic Beacon Falls Town Recreation Field, perfect for a day outdoors. With Naugatuck located about 5 miles from Middlebury, it serves as an ideal base for exploring the area. Choosing Naugatuck for your stay ensures a memorable and diverse experience.

Southbury

Southbury stands out as a prime spot for travelers interested in outdoor adventures and family fun. This charming city offers easy access to attractions like Quassy Amusement Park, Southford Falls State Park, and the scenic Candlewood Lake, making it a delightful destination for both couples and families. With its proximity at about 6 miles from Middlebury, Southbury is a smart choice for your stay, providing a perfect blend of recreation and relaxation.

Woodbury

Travelers visiting the area often choose Woodbury, especially families and those seeking a weekend getaway, drawn by its charming blend of outdoor activities and local attractions. With access to Quassy Amusement Park for fun-filled days, the scenic Hollow Park for relaxation, and the serene Abbey of Regina Laudis for a touch of tranquility, Woodbury provides a delightful escape. Located about 4 miles from Middlebury, it offers a smart choice for accommodations, ensuring a memorable stay in Connecticut.

Stay near popular attractions in and around Middlebury

Discover the charm of Middlebury, where family-friendly adventures await amidst stunning parks and historic sites. Enjoy outdoor activities and cultural experiences that create lasting memories for everyone. Explore the beauty of nature and the richness of history, making your stay truly unforgettable.

Learn more about Middlebury

Quassy Amusement Park offers thrilling rides and a refreshing lakeside beach where families cool off during summer months. History buffs can explore the 1800s buildings at Middlebury Historical Society Museum, while hikers enjoy scenic trails through Hop Brook Lake Park.

A multi-tiered waterfall cascading over dark rocks surrounded by lush greenery.

Top Middlebury Hotel Reviews

More cheap stays in Middlebury

Hotels in Middlebury with star-rating

Find out more about Middlebury

Top reasons to visit Middlebury

  • Family-Friendly Activities: Middlebury offers a range of attractions, including amusement parks and water parks, perfect for family fun.
  • Outdoor Adventures: Explore nearby national and urban parks, ideal for hiking and nature walks.
  • Charming City Center: Stroll through the picturesque Middlebury City Center, rich in history and local culture.
  • Diverse Accommodations: Choose from various hotels, including pet-friendly and agritourism options tailored for all travelers.
  • Relaxing Environment: Enjoy serene escapes at nearby campgrounds and peaceful spots like Middlebury Center Point.

Find great hotels near Middlebury

Explore a variety of hotel accommodations in Middlebury, Connecticut, perfect for your getaway. From pet-friendly options to welcoming spaces for LGBTQIA travelers, Middlebury offers diverse lodging choices. Whether you're visiting for business or leisure, you'll find hotels that cater to your needs, including agritourism properties that provide unique experiences. Discover the ideal Middlebury hotel for your stay and enjoy the charm of this quaint New England town.

  • Courtyard by Marriott Waterbury Downtown: Courtyard by Marriott Waterbury Downtown is a 3-star hotel with a guest rating of 8.4, offering a perfect blend of modern amenities and convenience just 5 miles from Middlebury. Ideal for both business and leisure travelers, this hotel features a variety of dining options, including a restaurant, coffee shop, and a snack bar. Active guests will appreciate the nearby mountain biking, hiking, and skiing facilities, while entertainment options like premium TV channels and flat-screen TVs ensure a comfortable stay. With easy access to a shopping district and local attractions, this hotel is an excellent choice for visitors looking to explore the area.
  • Wyndham Southbury: Wyndham Southbury is a 3-star hotel with a guest rating of 8.2, located 3 miles from Middlebury, making it an excellent option for business travelers and pet owners alike. This pet-friendly property allows pets on-site, making it a great choice for those traveling with furry companions. The hotel features practical amenities for business needs, ensuring a productive stay. With its welcoming atmosphere and convenient location, Wyndham Southbury offers a comfortable retreat for guests seeking both relaxation and connectivity.
  • La Quinta Inn & Suites by Wyndham Danbury: La Quinta Inn & Suites by Wyndham Danbury is a budget-friendly option with a guest rating of 8.4, situated 16 miles from Middlebury. Perfect for families and pet owners, this hotel provides child-friendly amenities like video game consoles and cribs at no extra charge. The property also welcomes pets, ensuring that no family member is left behind. Guests have praised the hotel's clean and comfortable environment, making it an ideal choice for those seeking value without sacrificing quality.

Where to stay near Middlebury

Experience the charm of Middlebury, Connecticut, where family-friendly adventures await. Explore the picturesque Middlebury City Center and the historic district, filled with friendly faces and rich history. For outdoor enthusiasts, nearby campgrounds in Southbury offer serene escapes. Discover the beauty of Middlebury Center Point, perfect for relaxing strolls and family gatherings. Whether you're seeking adventure or relaxation, Middlebury provides an ideal backdrop for unforgettable memories.

  • Waterbury: Located 5 miles from Middlebury, Waterbury is a vibrant city offering a mix of family-friendly activities and outdoor adventures. With visitor numbers peaking from April to June and July, it’s a great destination for those seeking a city-themed experience. Highlights include its educational venues, amusement parks, and resorts that cater to all ages. Don’t miss the local landmarks, such as the event conference venue, theme park, and waterpark, which provide endless entertainment options for both locals and tourists alike.
  • Southbury: Just 6 miles away from Middlebury, Southbury is a charming city known for its outdoor and romantic experiences. Visitors flock to this area primarily during the peak months of April to May and July. Southbury features a variety of attractions, including amusement parks and picturesque lakes that are perfect for family outings or a romantic getaway. Local landmarks like event conference venues and theme parks further enrich the travel experience, making Southbury an ideal spot for those looking to relax and enjoy nature.
  • Naugatuck: Situated 5 miles from Middlebury, Naugatuck offers a unique blend of outdoor adventure and family fun. With a steady flow of visitors throughout the year, the peak months are from April to May and July. This city is known for its educational venues, music concerts, and amusement parks that cater to thrill-seekers and families alike. Explore local landmarks such as the historic college university and national state park, which provide ample opportunities for exploration and adventure, ensuring a memorable visit.

Things to do in Middlebury

Middlebury, Connecticut, offers a delightful blend of family-friendly activities and outdoor adventures. Visitors can enjoy amusement parks and water parks, while also exploring local flea markets and shopping experiences. For those looking to unwind, there are options for indoor breaks and tennis courts available. Whether you're seeking excitement or relaxation, Middlebury has something to cater to every interest.

Shopping

In Middlebury, you can explore local shops like the Middlebury Antique Shop for unique finds. If you're up for a drive, visit the nearby Waterbury's Brass Mill Center for a variety of retail options, or check out the Westfield Meriden for popular brands and dining choices.

Recreation

In Middlebury, the Lake Quassapaug Retreat offers serene lakeside yoga sessions and holistic wellness workshops. Nearby, the Middlebury Spa provides rejuvenating massages and skincare treatments, creating a peaceful escape for relaxation and self-care.

Adventure

Explore the scenic trails at Middlebury's Fenn Mountain Park for hiking and birdwatching. Enjoy kayaking at Lake Quassapaug, where you can paddle through serene waters. For a thrilling experience, try the zip-lining at the nearby Adventure Park for an adrenaline rush among the trees.

Nightlife

In Middlebury, The Library is a cozy spot featuring live music and craft cocktails. For a lively atmosphere, check out The Greenway, where you can enjoy local brews and pub fare. Don’t miss the local wine bars for a relaxed evening with friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Middlebury

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Middlebury are January to March, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Middlebury is Tuesday. The most expensive day to stay in Middlebury is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia's search tool to refine your preferences, such as budget, desired location, and preferred hotel type. For instance, checking the Eco-certified option will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from low to high.
  • Consider bundling your trip: You can save money by booking an Expedia package that combines your hotel stay in Middlebury with your flights and activities.

Find the best attractions near Middlebury

Middlebury, Connecticut, is perfect for families and outdoor enthusiasts seeking adventure. The area boasts a variety of attractions, including national and urban parks, as well as amusement parks. Visitors can enjoy a mix of outdoor activities and cultural experiences, making it an ideal destination for travelers looking to explore nature and create lasting memories with loved ones.

  • Lake Compounce: Experience the thrill of Lake Compounce, a premier amusement park located 13 miles from Middlebury. With a variety of rides and attractions, it offers fun for the entire family amidst beautiful outdoor settings.
  • Beacon Falls Town Recreation Field: Just 6 miles away from Middlebury, this eco-friendly park is perfect for family outings. Enjoy its spacious grounds for picnics, sports, and recreational activities surrounded by nature.
  • Mattatuck Museum Arts and History Center: Located 5 miles from Middlebury, this arts center immerses you in local culture through its engaging exhibits, showcasing the rich history and artistic heritage of the region.

Best time to go to Middlebury

The best time to visit Middlebury is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.0°F (-2.2°C)Light RainMostly SunnyAverageSlightly Low
February29.7°F (-1.3°C)Light RainMostly CloudyAverageSlightly Low
March36.9°F (2.7°C)Light RainMostly SunnyAverageSlightly Low
April47.8°F (8.8°C)Light RainMostly SunnyModerately HighAverage
May58.5°F (14.7°C)Light RainMostly SunnyModerately HighSlightly High
June66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
July73.2°F (22.9°C)Light RainMostly SunnyModerately HighAverage
August71.6°F (22.0°C)Light RainMostly SunnyAverageAverage
September64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
October54.0°F (12.2°C)Light RainMostly SunnyModerately LowSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyModerately LowAverage
December34.3°F (1.3°C)Light RainMostly SunnyModerately LowAverage

The nearest major airports for your trip to Middlebury

Traveling to Middlebury, Connecticut, is convenient with several major airports nearby. New York's JFK Airport is 70 miles away, with nearby hotels like the 5-star Arlo Williamsburg and The William Vale, both only 11 miles from the airport. Newark Liberty International Airport (EWR) is 80 miles distant, featuring luxurious options such as The Dominick and Four Seasons Hotel, each located 9 miles from EWR. Lastly, LaGuardia Airport (LGA) is 65 miles away, with top-notch hotels like The Plaza and The Pierre, both 5 miles from the airport. These hotels offer various transportation services to ensure a smooth journey to your destination.

Frequently asked questions

What is the best area to stay in Middlebury?
The best area to stay in Middlebury, Connecticut is near the main commercial stretch of Route 64, specifically around the intersection with Route 63. This area offers convenient access to local amenities and the region's main thoroughfares.

Travelers looking for a comfortable and well-connected base will find this area ideal. It's home to several established hotels, providing reliable lodging options. From here, you're close to local dining establishments and shops, making it easy to grab a meal or any necessities.
When is the best time to go to Middlebury?
The best time to visit Middlebury is during the spring (late April to early June) and fall (September to October) when the weather is pleasant and the scenery is at its most appealing.

Springtime in Middlebury brings blooming flowers and lush greenery, making it an excellent time for outdoor activities like hiking and exploring nature reserves. The temperatures are mild, typically ranging from the mid-50s to mid-70s Fahrenheit, which is comfortable for walking around town or enjoying a round of golf.

Fall is particularly popular due to the stunning display of autumn foliage. The rolling hills surrounding Middlebury transform into a vibrant canvas of reds, oranges, and yellows. This season is ideal for scenic drives, visiting local farms, and enjoying apple picking.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Middlebury.
How much is the nightly rate at a Middlebury hotel?
Prices for hotels in Middlebury often vary, but you can find a great deal from $68 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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