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.
Courtyard by Marriott New Haven Orange-Milford

Courtyard by Marriott New Haven Orange-Milford

3 out of 5
Price was $295, price is now $272 per person
$272
per person
Feb 20 - Feb 23
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features a restaurant, an outdoor 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.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,412, price is now $1,355 per person
$1,355
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to New Haven (HVN)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.
Homewood Suites by Hilton Orange New Haven

Homewood Suites by Hilton Orange New Haven

3 out of 5
Price was $348, price is now $326 per person
$326
per person
Feb 20 - Feb 23
found 8 hours ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel features an indoor pool and a gym. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop and a safe deposit box are also provided.
Clarion Inn

Clarion Inn

3 out of 5
Price was $503, price is now $477 per person
$477
per person
Mar 29 - Mar 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
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.
Whitney Inn & Suites

Whitney Inn & Suites

2 out of 5
Price was $486, price is now $467 per person
$467
per person
Mar 29 - Mar 31
found 1 day ago
Roundtrip flight included
Chicago (ORD) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and luggage storage 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
$104 nightly
The price is $120 total per night
$120 total
Jan 25 - Jan 26
Total with taxes and fees
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
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Free Cancellation
$103 nightly
The price is $119 total per night
$119 total
Feb 8 - Feb 9
Total with taxes and fees
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
Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

2.5 out of 5
695 Bridgeport Ave Shelton CT
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $122 total per night
$122 total
Jan 23 - Jan 24
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.
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
$149 nightly
The price is $172 total per night
$172 total
Feb 8 - Feb 9
Total with taxes and fees
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
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
$86 nightly
The price is $99 total per night
$99 total
Jan 30 - Jan 31
Total with taxes and fees
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
Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd Farmington CT
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $92 total per night
$92 total
Feb 2 - Feb 3
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A safe deposit box is provided and the front desk is staffed around-the-clock.
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

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.

Quassy Amusement Park

Frequently asked questions

How much are vacation packages to Middlebury?
Travelocity offers flight and hotel vacation packages from just $272. 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

Either off access road at the end of Old Waterbury Rd, or Umberfield Rd. Abandoned in the woods near I 84 and power lines overhead.
Either off access road at the end of Old Waterbury Rd, or Umberfield Rd. Abandoned in the woods near I 84 and power lines overhead.

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