Deals on vacations and trips to Middlebury

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Middlebury flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
per person
Aug 14 - Aug 21
found 1 hour ago
Roundtrip non-stop flight included
Des Moines (DSM) to New Haven (HVN)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the in-room fitness and perks like free self parking.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Aug 14 - Aug 21
found 1 hour ago
Roundtrip non-stop flight included
Des Moines (DSM) to New Haven (HVN)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
per person
Aug 14 - Aug 21
found 1 hour ago
Roundtrip non-stop flight included
Des Moines (DSM) to New Haven (HVN)
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.
Homewood Suites by Hilton Wallingford-Meriden

Homewood Suites by Hilton Wallingford-Meriden

3 out of 5
per person
Aug 14 - Aug 21
found 1 hour ago
Roundtrip non-stop flight included
Des Moines (DSM) to New Haven (HVN)
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. Relax with a drink at the bar/lounge and enjoy free perks like on-the-go breakfast and free self parking.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
per person
Aug 14 - Aug 21
found 23 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to New Haven (HVN)
This aparthotel 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 hotels deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
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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.
Pet friendly
Free WiFi
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St, Waterbury, CT
Get rates
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.
Free WiFi
Restaurant
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
Free Cancellation
Reserve now, pay when you stay
Get rates
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.
Pool
Breakfast included
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
400 Sargent Dr, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Pet friendly
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane, Milford, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. 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.
Breakfast included
Pet friendly
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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

Quassy Amusement Park

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.

Quassy Amusement Park

Frequently asked questions

How much are vacation packages to Middlebury?
Travelocity offers flight and hotel vacation packages from just $821. With these kinds of bargains, you'll be exploring all of Middlebury before too long.
How long should my Middlebury vacation be?
Many travelers book their hotel for 2 nights in Middlebury. But that doesn't necessarily mean you're limited to that. How long you stick around really comes down to how much you want to see on your vacation. If you'd like to see every inch of this superb place, book another night or so (or even an extra week!).
Where can I get the best vacation package deals for Middlebury?
You can snap up awesome Middlebury package deals with Travelocity. Pick and choose from 400 air carriers and 1,000,000 properties worldwide and turn those vacation dreams into reality.
Why should I book my Middlebury vacation package with Travelocity?
Fantastic savings, loads of inspiring destinations and a team of customer service experts available 24/7 --- that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always score the best possible deal with Travelocity.
Can I save on my Middlebury car rental if I bundle it with hotels and flights?
With a Middlebury vacation package, you can bundle your flight, hotel and car bookings and save a nice amount. If you'd love to uncover the best of this fabulous part of the world, why not head to Times Square? This popular attraction is 70 mi from Middlebury. With your own wheels, you'll be there belong long.
Which airport is best for Middlebury?
Bradley Intl. Airport (BDL) is 35 mi from the downtown area and is the starting point for many exciting adventures. Alternatively, MacArthur Airport (ISP) is 50 mi away from central Middlebury and Tweed - New Haven Regional Airport (HVN) is 20 mi away from central Middlebury.
Where should I stay when visiting Middlebury?
Many people choose to spend their nights at the Traveler's Dream On Bike Path! Close to Highway, Hospitals, and Schools.. It's a terrific base for your Middlebury escape.

Photos of local treasures

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Photo by Brandon Miller
Photo by Brandon Miller