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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Save 100% on your flight
Price was $725, price is now $501 per person
$501
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Miami (MIA) 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 and barbecue grills are also provided.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $4,256, price is now $2,540 per person
$2,540
per person
Jul 1 - Jul 8
found 21 hours ago
Roundtrip flight included
Miami (MIA) 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.
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,445, price is now $1,048 per person
$1,048
per person
Jun 19 - Jun 21
found 13 hours ago
Roundtrip flight included
Fort Myers (RSW) to New Haven (HVN)
This smoke-free 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.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $1,660, price is now $1,367 per person
$1,367
per person
May 15 - May 17
found 23 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
Price was $1,105, price is now $940 per person
$940
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free local cuisine breakfast each morning. A garden and express check-out are 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
$105 nightly
The price is $121 total per night
$121 total
May 3 - May 4
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
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $115 total per night
$115 total
Apr 19 - Apr 20
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
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
$163 nightly
The price is $187 total per night
$187 total
Apr 22 - Apr 23
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
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
$118 nightly
The price is $136 total per night
$136 total
Apr 26 - Apr 27
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 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
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $175 total per night
$175 total
Apr 26 - Apr 27
Total with taxes and fees
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
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $136 total per night
$136 total
Apr 23 - Apr 24
Total with taxes and fees
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.
Pool
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(15 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 $501. 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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Middlebury

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