Prices and availability subject to change. Additional terms may apply.
Holiday Inn Express Southington, an IHG Hotel
2.5 out of 5
Price was $499, price is now $430 per person
$430
per person
May 31 - Jun 3
Roundtrip non-stop flight included
Roanoke (ROA) to New Haven (HVN)
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Madison Beach Hotel
4 out of 5
Madison Center
Price was $1,185, price is now $1,034 per person
$1,034
per person
May 31 - Jun 3
Roundtrip non-stop flight included
Roanoke (ROA) to New Haven (HVN)
This hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.
Hilton Garden Inn Hartford North/Bradley Int'l Airport
3 out of 5
Price was $513, price is now $467 per person
$467
per person
May 31 - Jun 3
Roundtrip non-stop flight included
Roanoke (ROA) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.
Fairfield by Marriott Inn & Suites Wallingford New Haven
2.5 out of 5
Price was $530, price is now $485 per person
$485
per person
May 31 - Jun 3
Roundtrip non-stop flight included
Roanoke (ROA) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Luxury Apartments by Hyatus at Pierpont
4 out of 5
The Hill
Price was $886, price is now $870 per person
$870
per person
May 31 - Jun 3
Roundtrip non-stop flight included
Roanoke (ROA) to New Haven (HVN)
This apartment features a 24-hour gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Top Middlebury hotel deals
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
The price is $159 per night
$159
per night
May 26 - May 27
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Hilton Garden Inn Shelton
3 out of 5
25 Old Stratford Rd, Shelton, CT
Free Cancellation
Reserve now, pay when you stay
The price is $110 per night
$110
per night
May 6 - May 7
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Cambria Hotel New Haven University Area
3 out of 5
20 Dwight Street, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
The price is $144 per night
$144
per night
May 26 - May 27
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.
Holiday Inn Express Southington, an IHG Hotel
2.5 out of 5
120 Laning St, Southington, CT
Free Cancellation
The price is $121 per night
$121
per night
Apr 28 - Apr 29
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
Free Cancellation
Reserve now, pay when you stay
The price is $89 per night
$89
per night
Apr 28 - Apr 29
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a coffee shop are also offered.
Best Western Executive Hotel Of New Haven - West Haven
2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Free Cancellation
Reserve now, pay when you stay
The price is $105 per night
$105
per night
Apr 28 - Apr 29
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
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.
Popular places to visit in Middlebury
Quassy Amusement Park
4.5/5(13 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.
Travelocity offers package deals to Middlebury, including flights and hotels, starting at just $430. With all that extra money, you could include some awesome tours or possibly even add a couple of extra days to your getaway.
How long should my Middlebury vacation be?
Most visitors stay in Middlebury for approximately 2 nights. That said, travel is all about checking out new things and creating unforgettable memories — why not book a couple of extra nights so you can do just that?
Where can I get the best vacation package deals for Middlebury?
Travelocity can help you lock in an unbeatable Middlebury package deal. With 400 airlines and 1,000,000 properties worldwide, we’re sure you’ll be able to craft the perfect itinerary.
Why should I purchase my Middlebury vacation bundle via Travelocity?
From our 24/7 customer care to our range of exciting destinations, we are dedicated to giving you the most unforgettable escape. All you have to do is click and book — our Price Match Guarantee will ensure you score the best deal.
Can I save money on my Middlebury car rental if I bundle it with a hotel or flight?
Bundling your hotel, car and flight into a Middlebury vacation package is the best way to land the best prices. Plus, having your own rental car gives you absolute freedom to make your way to all those big sights you’d like to check out. Sitting 70 mi away from Middlebury, Times Square is one attraction that should feature on your itinerary. Fasten your seat belt and make a day trip of it.
What is the best time of year to go to Middlebury?
If you want to avoid costly flights, big crowds and full hotels, plan your getaway outside of June, July and August. The quietest time to be in Middlebury is December, January and February. You’ll find the highest hotel prices in and the lowest in .
Which airport is best for Middlebury?
It’s likely you’ll be arriving at Bradley Intl. Airport (BDL), situated 35 mi northeast of inner Middlebury. Westchester County Airport (HPN) (45 mi away from central Middlebury) and MacArthur Airport (ISP) (50 mi away from central Middlebury) are your other choices.
What is there to do in Middlebury?
Quassy Amusement Park should be toward the top of your travel schedule. After you’ve crossed off this popular attraction, simply stroll the streets of Middlebury and find out what makes this fantastic city tick.