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.
Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London

2 out of 5
Price was CA $955, price is now CA $881 per person
CA $881
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
7/10 Good! (1,005 reviews)
Close to Mohegan Sun which was the reason for our visit. For the most part it was decently clean. Front desk staff was friendly. Parking was easy. Very convenient and decently priced.

Reviewed on Aug. 28, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was CA $2,382, price is now CA $1,863 per person
CA $1,863
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
No reviews
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Price was CA $1,293, price is now CA $1,145 per person
CA $1,145
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.8/10 Excellent! (1,737 reviews)
This hotel is somewhat dated. That being said, it is clean, convenient location, good customer service, and very good pricing.

Reviewed on Aug. 28, 2025

Sleep Inn & Suites Niantic

Sleep Inn & Suites Niantic

2.5 out of 5
Price was CA $1,154, price is now CA $1,058 per person
CA $1,058
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
8.4/10 Very Good! (1,002 reviews)
stayed 2 nights. no complaints. kids appreciated the pool

Reviewed on Aug. 26, 2025

The Niantic Inn

The Niantic Inn

2 out of 5
Price was CA $1,447, price is now CA $1,352 per person
CA $1,352
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to New Haven (HVN)
9.2/10 Wonderful! (103 reviews)
Superlatively clean! Fresh flowers left in room. Very quiet location and easy parking. Excellent management resolved confusion caused by Expedia. Book directly with Niantic Inn and get free beach pass! Walkable to best Niantic beaches and restaurants.

Reviewed on Aug. 20, 2025

Ready to book your vacation to Middlebury?

 

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Middlebury Hotel Deals

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 7 to Sep 8
CA $210
CA $241 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"The best"

Reviewed on Aug. 27, 2025

Trumbull Marriott Shelton
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 $141 per night from Sep 24 to Sep 25
CA $141
CA $162 total
Sep 24 - Sep 25
includes taxes & fees
7.8/10 Good! (1,304 reviews)
"Staff was very friendly and knowledgeable of the area."

Reviewed on Aug. 22, 2025

Best Western Executive Hotel Of New Haven - West Haven
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 21 to Sep 22
CA $197
CA $227 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (1,013 reviews)
"Walkable to Yell. Good service. But no free internet"

Reviewed on Aug. 27, 2025

Omni New Haven Hotel at Yale
See all 964 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
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Family Vacations
Family Vacations

Frequently asked questions

How much does a Middlebury vacation package cost?
Offering great value package deals from CA $881 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.