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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, (1,335 reviews)
"Very nice and comfortable stay, room is very clean, the hotel restaurant is awesome & convenient."
United States
Catherine
The price is £75
includes taxes & fees
6 Dec - 7 Dec
Wyndham Southbury

2. Hampton Inn Waterbury

Hampton Inn Waterbury
2.5 star property
Waterbury
8.0 out of 10, Very good, (1,001 reviews)
"always stay here. great staff, breakfast and room."
United States
John
The price is £90
includes taxes & fees
15 Nov - 16 Nov
Hampton Inn Waterbury

3. Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown
3.0 star property
Waterbury
8.6 out of 10, Excellent, (1,293 reviews)
"I would definitely stay there again"
United States
Ludim
The price is £76
includes taxes & fees
8 Nov - 9 Nov
Courtyard by Marriott Waterbury Downtown

4. Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center
3.5 star property
Southbury
8.4 out of 10, Very good, (1,002 reviews)
"A great place for a one-night stop."
United States
Louise
The price is £105
includes taxes & fees
18 Nov - 19 Nov
Heritage Hotel, Golf & Conference Center

5. The Milestone Inn

The Milestone Inn
2.5 star property
Woodbury
8.8 out of 10, Excellent, (215 reviews)
"Great place!"
United States
Roxanna
The price is £80
includes taxes & fees
9 Nov - 10 Nov
The Milestone Inn

6. Quality Inn Waterbury East

Quality Inn Waterbury East
2.5 star property
Waterbury
7.0 out of 10, Good, (1,000 reviews)
"perfect place to stay all clean"
United States
Wilfred
The price is £72
includes taxes & fees
15 Nov - 16 Nov
Quality Inn Waterbury East

7. Comfort Inn Naugatuck-Shelton, CT

Comfort Inn Naugatuck-Shelton, CT
2.5 star property
Naugatuck
8.0 out of 10, Very good, (867 reviews)
"Overall this is a great place to stay and I would stay there again. I wish our room had a microwave and there was a bigger breakfast selection. But the beds were comfy and the room was clean."
United States
Kimberly
The price is £84
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn Naugatuck-Shelton, CT

8. Waterbury Motel

Waterbury Motel
2.0 star property
Waterbury
3.8 out of 10, (240 reviews)
"Filthy room, graffiti, paint peeling, strong smoke order, roaches running across the floor. Where do I begin"
United States
Rayquan
The price is £50
includes taxes & fees
9 Nov - 10 Nov
Waterbury Motel

9. Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG
3.0 star property
Southington
8.2 out of 10, Very good, (1,002 reviews)
"Breakfast was delicious and breakfast staff was very nice and very friendly!"
United States
DAVID
The price is £85
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Cheshire - Southington by IHG

10. Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG
2.5 star property
Southington
8.6 out of 10, Excellent, (1,468 reviews)
"Good breakfast Clean room Perfect for a stay"
Canada
Guillaume
The price is £78
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Express Southington by IHG

11. Cheshire Welcome Inn

Cheshire Welcome Inn
2.5 star property
Cheshire
8.4 out of 10, Very good, (901 reviews)
"Quaint roadside motel"
United States
Jessica
The price is £76
includes taxes & fees
10 Nov - 11 Nov
Cheshire Welcome Inn

12. DoubleTree by Hilton Hotel Bristol, Connecticut

DoubleTree by Hilton Hotel Bristol, Connecticut
4.0 star property
Bristol
9.0 out of 10, Wonderful, (1,000 reviews)
"Lovely stay, easy check in and kind staff. The room was clean and comfortable"
United States
Julia
The price is £121
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Hotel Bristol, Connecticut

13. Econo Lodge Milldale - Southington

Econo Lodge Milldale - Southington
2.0 star property
Milldale
6.6 out of 10, (610 reviews)
"Parking"
United States
LUIS
The price is £54
includes taxes & fees
29 Nov - 30 Nov
Econo Lodge Milldale - Southington

14. Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol
3.0 star property
Bristol
9.6 out of 10, Exceptional, (285 reviews)
"Everything was wonderful , we enjoy a lot the hot tub and the go to pool that feels amazing"
United States
Gabriela
The price is £111
includes taxes & fees
15 Nov - 16 Nov
Home2 Suites by Hilton Bristol

15. Courtyard by Marriott Southington

Courtyard by Marriott Southington
3.0 star property
Southington
8.8 out of 10, Excellent, (510 reviews)
"Very nice clean hotel, in a good location, near food spots."
United States
Raeshell
The price is £145
includes taxes & fees
20 Nov - 21 Nov
Courtyard by Marriott Southington

16. PLYMOUTH MOTOR LODGE

PLYMOUTH MOTOR LODGE
2.5 star property
Terryville
7.6 out of 10, Good, (223 reviews)
"There are no many options to stay over in that area so we had to stay there. This place is to be used by couples for a few hours. Bathroom, floors, walls, bed, etc. Discussing. We brought our own sheets just in case and I’m glad we did. Don’t stay here if you can avoid it."
United States
Danitza
The price is £75
includes taxes & fees
8 Dec - 9 Dec
PLYMOUTH MOTOR LODGE

17. Rocky River Inn

Rocky River Inn
3.0 star property
New Milford
8.6 out of 10, Excellent, (955 reviews)
"If you're looking for a place to stay to explore western Connecticut, you found it."
United States
James
The price is £110
includes taxes & fees
8 Nov - 9 Nov
Rocky River Inn

18. Days Inn by Wyndham Southington

Days Inn by Wyndham Southington
2.0 star property
Southington
7.8 out of 10, Good, (1,001 reviews)
"The staff are extremely nice and professional. The rooms are very clean and comfortable"
United States
Elizabeth
The price is £74
includes taxes & fees
6 Dec - 7 Dec
Days Inn by Wyndham Southington

19. La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury
3.0 star property
Danbury
8.4 out of 10, Very good, (841 reviews)
"We had a brief stay and staff was super friendly and the bed was comfortable."
United States
Jennifer
The price is £97
includes taxes & fees
6 Dec - 7 Dec
La Quinta Inn & Suites by Wyndham Danbury

20. Hampton Inn & Suites By Hilton North Haven

Hampton Inn & Suites By Hilton North Haven
2.5 star property
North Haven
9.4 out of 10, Exceptional, (135 reviews)
"The location is great. Next to plenty of stores and restaurants The breakfast was great and a variety."
United States
TRINA
The price is £103
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites By Hilton North Haven
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.

Where to stay in Middlebury

Find the best Middlebury areas for the activities you enjoy most.

Middlebury Center Historic District

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

Stay near popular Middlebury attractions

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

Find out more about Middlebury

Top reasons to visit Middlebury

  • Outdoor Adventures: Middlebury offers thrilling outdoor activities, including hiking, picnicking, and exploring scenic parks and lakes.
  • Family-Friendly Attractions: Enjoy exciting rides at local amusement parks and splashes at water parks, perfect for family outings.
  • Charming New England Atmosphere: Stroll through quaint streets, experiencing the warm hospitality and historical treasures of this picturesque town.
  • Diverse Accommodation Options: Choose from a variety of hotels, including pet-friendly and business-themed properties for a comfortable stay.
  • Cultural Experiences: Engage with local culture and enjoy the friendly atmosphere, making every visit memorable.

Find great hotels near Middlebury

Discover a variety of accommodation options in Middlebury, Connecticut, catering to every traveller's needs. Whether you're seeking a pet-friendly hotel for a family getaway or a business-themed property for your work trip, Middlebury has something for everyone. Explore the charming Middlebury Inn and its inviting rooms, or uncover other delightful hotels in the area that promise a comfortable and memorable stay.

  • Courtyard by Marriott Waterbury Downtown: Nestled a mere 3.1km from Middlebury, Courtyard by Marriott Waterbury Downtown is a vibrant 3-star hotel that warmly welcomes LGBTQIA travellers. This contemporary establishment features a modern lobby, inviting communal spaces, and spacious rooms designed for relaxation. Guests can unwind in the indoor pool or stay active in the fitness centre. The hotel’s bistro offers a delightful range of meals and beverages, making it a perfect spot for casual dining. With a commitment to inclusivity and comfort, this hotel is an ideal choice for those seeking a friendly and welcoming atmosphere.
  • Wyndham Southbury: Located just 1.9km from Middlebury, Wyndham Southbury is a 3-star hotel that caters to both business and leisure travellers. This pet-friendly property provides essential amenities for business guests, including a fully equipped Business Centre and multiple meeting rooms. After a day of meetings or exploring the surrounding area, guests can relax in comfortable accommodations, and for those travelling with pets, the hotel offers specific amenities to ensure a pleasant stay. Its convenient location and comprehensive services make it an excellent choice for professionals and families alike.
  • Microtel Inn & Suites by Wyndham Bethel/Danbury: Situated 9.9km from Middlebury, Microtel Inn & Suites by Wyndham Bethel/Danbury combines comfort with a business-friendly environment and LGBTQIA inclusivity. This hotel features a 24-hour Business Centre, conference space, and multiple meeting rooms, catering to the needs of professionals. The pet-friendly policy allows for a hassle-free stay for guests with furry companions, while amenities like complimentary breakfast ensure a pleasant start to your day. With its welcoming atmosphere and versatile facilities, this hotel is perfect for both work and leisure.

Where to stay near Middlebury

Middlebury, Connecticut, is a charming destination perfect for families and adventure seekers alike. Stroll through the quaint streets of this New England gem, where you’ll experience the warm embrace of local hospitality. Explore the picturesque town on foot, uncovering its historical treasures and enjoying the friendly atmosphere. Whether you seek outdoor activities or a relaxing escape, Middlebury offers a delightful blend of experiences for every traveller.

  • Waterbury: Located a mere 3.1km from Middlebury, Waterbury is a vibrant city known for its family-friendly atmosphere and outdoor adventures. The travel experience here is enriched by a variety of attractions, including educational venues, resorts, and amusement parks. Visitors often flock to the local theme park and waterpark, making it a lively hub of fun, especially during peak months from April to July. With its blend of urban and natural experiences, Waterbury is perfect for families seeking memorable excursions.
  • Southbury: Just 3.7km away from Middlebury, Southbury is an inviting city that promises outdoor activities and romantic getaways. The travel experience is characterised by its charming resorts and enjoyable amusement parks, complemented by beautiful lakeside views. Peak visitor numbers occur from April to May and in July, making it an ideal time for families and couples alike to explore the local theme park and event venues. Southbury’s laid-back vibe and scenic landscapes create an enchanting atmosphere for all who visit.
  • Woodbury: Situated 2.5km from Middlebury, Woodbury offers a picturesque escape that is perfect for those who appreciate outdoor activities and romantic scenery. The city is known for its ski fields and shopping centres, making it a versatile destination. With visitor peaks in April to May and July, Woodbury attracts those looking to enjoy its beautiful lakes and the nearby national state park. This charming city provides a delightful mix of adventure and tranquillity, ideal for a refreshing getaway.

Things to do near Middlebury

Middlebury is perfect for outdoor family adventures, offering a variety of activities to delight visitors. Enjoy thrilling rides at the amusement park, splash around at the water park, or explore the scenic recreational areas. Whether you're seeking excitement or relaxation, Middlebury has something for everyone to enjoy during your holiday.

Shopping

The nearest shopping destination is Brass Mill Center, only 3.7km away, offering a variety of shops and family entertainment. If you're up for a drive, check out Maplecroft Plaza Shopping Center, located 7.5km from Middlebury, for more city and family vibes. Lastly, the Elephant's Trunk Flea Market is 9.3km away, perfect for unique finds.

Recreation

Yale Golf Course, located 9.9km from Middlebury, offers a picturesque setting for golf enthusiasts, surrounded by lush greenery. For a tranquil experience, Kettletown State Park, 5.0km away, invites relaxation amidst nature. The Cullman-Heyman Tennis Center, 10.6km distant, provides a vibrant atmosphere for tennis lovers.

Adventure

Experience thrilling skiing at Woodbury Ski Area, located 5.0km from Middlebury, where the slopes cater to all skill levels. For water sports enthusiasts, Waterski Connecticut, 8.1km away, offers exhilarating water skiing adventures. Enjoy a scenic hike along the Big Cathedral Trail, situated 9.3km from Middlebury, immersing yourself in nature.

Nightlife

For a delightful evening in Middlebury, catch a show at the Palace Theatre, only 3.1km away, offering a charming mix of entertainment and culture. Alternatively, venture to Crystal Bees, 13.1km away, for family fun and adventure, or enjoy a romantic film at Cinemark North Haven, 11.2km away.

Booking tips and Expedia advantages for Middlebury

For a budget-friendly visit to Middlebury, consider travelling between January and March when accommodation prices are lower. Mondays are the cheapest days to stay, while Saturdays are the priciest. Use Expedia to compare hotel options and filter by price to find the best deals. Look into package deals that combine flights, hotels, and activities to save even more. Additionally, explore free local attractions and utilise public transport to keep costs down during your stay.

  • 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 Monday. The most expensive day to stay in Middlebury is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, preferred location, and the type of hotel that suits you best. To uncover the most affordable prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can enjoy savings by combining your Middlebury hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Middlebury

Middlebury, Connecticut, offers a delightful mix of outdoor and family-friendly activities, making it an ideal spot for adventure vacations. Visitors can explore national and urban parks, as well as picturesque lakes. Key attractions include Middlebury Park and other popular local sites, catering to those seeking a blend of outdoor fun and cultural experiences. Whether you’re hiking, picnicking, or enjoying the scenic beauty, there's plenty to discover in and around Middlebury.

  • Lake Compounce: Experience the thrill of Lake Compounce, an amusement park that offers a variety of rides and family-friendly attractions. Nestled in a scenic setting, it promises outdoor adventures and fun for all ages, making it a perfect day out for families.
  • Indian Well State Park: Discover the natural beauty of Indian Well State Park, where you can enjoy picturesque scenery and exhilarating outdoor activities. With its stunning views and hiking trails, it's a fantastic spot for adventure lovers and nature enthusiasts alike.
  • Lake Quassapaug: Relax at Lake Quassapaug, a tranquil lake ideal for a romantic getaway or a family picnic. With its beautiful beach and serene surroundings, it offers the perfect setting for outdoor activities and leisurely days by the water.

Best time to go to Middlebury

The best time to visit Middlebury can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Middlebury falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Middlebury falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January28.0°F (-2.2°C)Light RainMostly SunnyAverageSlightly Low
February29.7°F (-1.3°C)Light RainMostly CloudyAverageAverage
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 HighAverage
June66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
July73.2°F (22.9°C)Light RainMostly SunnyModerately HighSlightly High
August71.6°F (22.0°C)Light RainMostly SunnyAverageSlightly High
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 LowSlightly Low
December34.3°F (1.3°C)Light RainMostly SunnyModerately LowAverage

The nearest major airports for your trip to Middlebury

When visiting Middlebury, Connecticut, you can fly into several major airports. Bradley International Airport (BDL) in Hartford, situated 22.4km away, offers convenient access. Recommended hotels nearby include the DoubleTree by Hilton Hartford - Bradley Airport, just 621m from BDL, and the Marriott Hartford Downtown, located 7.5km away. Additionally, Westchester County Airport (HPN) in White Plains, 27.3km from Middlebury, has excellent hotel options like The Opus Westchester and Sonesta White Plains Downtown, both 2.5km from HPN. Islip MacArthur Airport (ISP), 5621ms away, features the Hyatt Regency Long Island, situated 2.5km from ISP. All these hotels provide accessible transportation to their respective airports.

Frequently Asked Questions

What is the best area to stay in Middlebury?

The best area to stay in Middlebury, Connecticut, is near the historic Middlebury Green, which offers the most convenient and well-appointed options.

This central area is the heart of the town, featuring the iconic Middlebury Green itself, surrounded by historic buildings and local businesses. It's a pleasant, walkable part of town, providing easy access to local amenities and a sense of community. The main thoroughfare, Route 64 (Middlebury Road), runs nearby, connecting you to other local attractions.

Couples looking for a relaxing getaway will appreciate staying near the Green. The area provides a quiet setting with opportunities for gentle strolls, and some accommodations offer amenities like spa services or fine dining on-site, superb for a peaceful escape.

For those travelling for business or looking for a convenient base to explore the wider region, staying near the Green also offers practical advantages.

When is the best time to go to Middlebury?

The best time to visit Middlebury, Connecticut, is during the autumn months, particularly from late September to late October.

This period offers pleasant weather with comfortable temperatures, great for exploring the outdoors. The main draw is the spectacular fall foliage, as the surrounding hillsides transform into a canvas of red, orange, and gold. It's a wonderful time for scenic drives and enjoying the natural beauty of the region.

Couples often find this time ideal for a romantic getaway, perhaps enjoying strolls through local orchards or visiting vineyards. The crisp air and stunning scenery create a memorable backdrop for exploring the quieter side of Connecticut.

For families, the autumn also brings opportunities for seasonal activities like pumpkin picking and corn mazes at local farms, adding a fun, festive element to their trip.

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 £50 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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