Middlebury Vacation Packages

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Your Middlebury Vacation

You'll find plenty to like about Middlebury, from its rich history to its cultural experiences. When you're ready to say hello to this fascinating city, our Middlebury vacation packages are calling your name. A trip to Middlebury is a terrific opportunity to sightsee. Be sure to visit popular attractions like Quassy Amusement Park, Palace Theatre and Brass Mill Center. No matter your travel plans or budget, organizing your ultimate tailored Middlebury vacation is a breeze with Expedia.

Top Middlebury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was CA $652, price is now CA $585 per person
CA $585
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8/10 Very good! (1,664 reviews)
．

Reviewed on Jun 30, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,344, price is now CA $1,092 per person
CA $1,092
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was CA $846, price is now CA $700 per person
CA $700
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.2/10 Wonderful! (2,194 reviews)
A basic property, but clean and well-maintained and convenient to New Haven.

Reviewed on Jun 30, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was CA $929, price is now CA $797 per person
CA $797
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.

Reviewed on Jun 2, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was CA $854, price is now CA $738 per person
CA $738
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
8.6/10 Excellent! (1,316 reviews)
Room was ok. The drains were clogged so made showering a bit difficult

Reviewed on Jun 30, 2026

Ready to book your vacation to Middlebury?

 

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Middlebury Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Jul 7 to Jul 8
CA $158
CA $182 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (2,209 reviews)
"A basic property, but clean and well-maintained and convenient to New Haven."

Reviewed on Jun 30, 2026

New Haven Hotel
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Jul 5 to Jul 6
CA $161
CA $185 total
Jul 5 - Jul 6
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"I came to CT because my brother passed away. • Upon arrival, my room was nearly 80 degrees. When I requested another room, I was told that was not possible. Maintenance eventually arrived and determined that the thermostat had simply been left on “heat” instead of “cool.” This should have been identified ..."

Reviewed on Jun 30, 2026

Hilton Garden Inn Milford
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
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 7 to Jul 8
CA $147
CA $168 total
Jul 7 - Jul 8
includes taxes & fees
8/10 Very good! (1,691 reviews)
"．"

Reviewed on Jun 30, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,089 properties in Middlebury
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.
All Inclusive Vacations
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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 does a Middlebury vacation package cost?
Offering great value package deals from CA $585 on Expedia, you'll be pleasantly surprised at how much a vacation to Middlebury costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Middlebury?
You can usually find lower rates and greater availability in January, February and March. Check out our cheap Middlebury vacation packages and you could get some great off-season deals.
How many days is enough for Middlebury?
Dedicate at least 2 days for your Middlebury vacation to enjoy everything that makes this destination special. Explore key areas, including Middlebury Centre Historic District and Oakville. Then tick off top sights like Lake Quassapaug and Southford Falls State Park. With a clever itinerary, you can keep busy with room for some relaxation too. Want to travel outside of Middlebury? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Middlebury?
Well known for its golfing and home to popular attractions like Middlebury Centre Historic District, a Middlebury vacation is sure to leave an impression. Another top sight to visit? Don't miss Quassy Amusement Park.
How to find the best Middlebury package deals?
Use Expedia's filter tool to help you find some of the best Middlebury package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Middlebury package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Middlebury vacation as a package?
You can enjoy significant savings on your next Middlebury escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Middlebury?
If you're considering a spur-of-the-moment Middlebury getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Middlebury?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Middlebury.
  2. Budget wisely: Besides the price of your hotel, you should consider other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may come up during your trip to Middlebury.
  3. Decide your trip length: Consider how long you'd like to spend discovering Middlebury. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Middlebury vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.