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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.8/10 Good! (987 reviews)
Overall was Good Bed was Comfortable Room had musty smell

Reviewed on Jul. 13, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
Beautiful spot and great accommodations—can’t wait to return!

Reviewed on Jul. 13, 2025

Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
Westbrook Center
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
10/10 Exceptional! (151 reviews)
It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable.

Reviewed on Mar. 20, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Aug 30 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
8.8/10 Excellent! (1,014 reviews)
Everything was great, the rooms where clean, the staff was awesome

Reviewed on Jul. 9, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Aug 30 - Sep 1
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
8.8/10 Excellent! (412 reviews)
It was close to shopping and restaurants.

Reviewed on May 2, 2025

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 $177 per night from Jul 28 to Jul 29
CA $177
CA $204 total
Jul 28 - Jul 29
includes taxes & fees
8.8/10 Excellent! (1,651 reviews)
"My family has stayed here a few times and we have always found it clean and comfortable. It was a little noisy this visit, but the bed was comfortable so we still all slept great."

Reviewed on Jul. 13, 2025

New Haven Hotel
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 $131 per night from Jul 20 to Jul 21
CA $131
CA $151 total
Jul 20 - Jul 21
includes taxes & fees
7.6/10 Good! (1,190 reviews)
Nice hotel terrible service from staff
"Room was great. Pool was clean. Breakfast was nice. The staff during the day was very rude primarily this one lady who was working pretty much every day shift. She wasn’t friendly and she didn’t want to be any help when I asked her if I could get any video footage of the parking lot so I could possibly ..."

Reviewed on Jul. 12, 2025

Best Western Executive Hotel Of New Haven - West Haven
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
3 out of 5
400 Sargent Dr, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 20 to Jul 21
CA $147
CA $169 total
Jul 20 - Jul 21
includes taxes & fees
5.8/10 (1,017 reviews)
"The place was quiet and near to local shops"

Reviewed on Jul. 3, 2025

La Quinta Inn & Suites by Wyndham New Haven
See all 955 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Middlebury vacation package cost?
Offering great value package deals from CA $477 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.

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