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 $549, price is now $438 per person
$438
per person
Nov 6 - Nov 8
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) 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.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,496, price is now $780 per person
$780
per person
Nov 6 - Nov 8
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) 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.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $925, price is now $714 per person
$714
per person
Nov 6 - Nov 8
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $620, price is now $500 per person
$500
per person
Nov 6 - Nov 8
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
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.
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $686, price is now $558 per person
$558
per person
Nov 6 - Nov 8
found 19 hours ago
Roundtrip flight included
Raleigh (RDU) 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.

Top Middlebury hotels deals

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $171 total per night
$171 total
Sep 2 - Sep 3
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
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
$118 nightly
The price is $136 total per night
$136 total
Sep 7 - Sep 8
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
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
$114 nightly
The price is $131 total per night
$131 total
Sep 16 - Sep 17
Total with taxes and fees
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
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
$142 nightly
The price is $163 total per night
$163 total
Sep 6 - Sep 7
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
$135 nightly
The price is $155 total per night
$155 total
Sep 9 - Sep 10
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
Hampton Inn & Suites New Haven - South - West Haven

Hampton Inn & Suites New Haven - South - West Haven

2.5 out of 5
510 Saw Mill Rd West Haven CT
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $132 total per night
$132 total
Sep 7 - Sep 8
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the express check-in and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
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.

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 $438. 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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