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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $485, price is now $402 per person
$402
per person
Aug 14 - Aug 16
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,181, price is now $933 per person
$933
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $993, price is now $801 per person
$801
per person
Aug 14 - Aug 16
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was $539, price is now $452 per person
$452
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip flight included
Las Vegas (LAS) to New Haven (HVN)
Free WiFi in public areas is available at this hotel. Business travelers can take advantage of the business center. Take advantage of the free self parking.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $667, price is now $562 per person
$562
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip flight included
Las Vegas (LAS) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.

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
The price is $155 total per night
$155 total
per night
Jul 26 - Jul 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.
Pet friendly
Free WiFi
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Free Cancellation
Reserve now, pay when you stay
The price is $175 total per night
$175 total
per night
Jul 26 - Jul 27
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, bar/lounge, and laundry facilities.
Pool
Hot Tub
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
The price is $131 total per night
$131 total
per night
Jul 19 - Jul 20
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
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
The price is $112 total per night
$112 total
per night
Aug 2 - Aug 3
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.
Pool
Breakfast included
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
The price is $163 total per night
$163 total
per night
Aug 9 - Aug 10
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. 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.
Pet friendly
Free WiFi
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Free Cancellation
The price is $161 total per night
$161 total
per night
Jul 27 - Jul 28
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.
Pet friendly
Free WiFi
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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.

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.
See properties

Frequently asked questions

How much are vacation packages to Middlebury?
Travelocity offers flight and hotel vacation packages from just $402. 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

Browse Middlebury vacation photos for more inspiration

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

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