Litchfield Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Jennifer Magri

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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Find the Best Litchfield Vacation Packages

Litchfield Hotel Deals

The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road, Litchfield, CT
The price is ￥45,131 per night from Aug 18 to Aug 19
￥45,131
￥51,901 total
Aug 18 - Aug 19
includes taxes & fees
9/10 Wonderful! (930 reviews)
"Breakfast could have been better"

Reviewed on Jul 25, 2025

The Litchfield Inn
The Abner Hotel

The Abner Hotel

3 out of 5
15 West St, Litchfield, CT
The price is ￥38,535 per night from Sep 1 to Sep 2
￥38,535
￥44,315 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (30 reviews)
"Would be great to have a coffee maker in room, or some room service options."

Reviewed on Jul 29, 2025

The Abner Hotel
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is ￥13,693 per night from Aug 20 to Aug 21
￥13,693
￥15,747 total
Aug 20 - Aug 21
includes taxes & fees
8/10 Very Good! (1,014 reviews)
"It was a beautiful stay room was very clean check in was very easy staff was very professional and sweet thank u we will see ya again"

Reviewed on Aug 11, 2025

Wyndham Southbury
See all 730 properties in Litchfield
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.

Frequently asked questions

How much does a Litchfield vacation package cost?
You'll find cheap prices on Expedia for your Litchfield escape. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Litchfield costs.
What are the cheapest months to go to Litchfield?
If you're looking to score a cheap Litchfield vacation package, consider visiting in January, February and November. You'll typically find better rates on flights and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Litchfield?
Litchfield vacations come in all shapes and sizes, but to really sink your teeth into this destination, we reckon 2 days is about right. This will mean you can visit top attractions like Haight-Brown Vineyard and Litchfield Historical Society Museum along with underrated spots. Don't forget to explore cool neighborhoods such as Litchfield Historic District and Milton Center Historic District either. If you're smart with your time, you can even allow for a day trip or two from Litchfield too.
Is it worth booking a vacation package to Litchfield?
Whether you're planning to explore attractions such as Litchfield Town Green and White Memorial Conservation Center, or eager to experience its top-notch history and nature, a Litchfield vacation will leave you with lasting memories. Book your getaway with Expedia and discover why Litchfield is such a good vacation destination.
How to find the best Litchfield package deals?
Bagging a cheap Litchfield package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most affordable Litchfield package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Litchfield vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Litchfield vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Litchfield?
If you have your Litchfield travel dates confirmed, book early to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for traveling on a whim.
How to plan a trip to Litchfield?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to visit Litchfield.
  2. Work out your budget: Ensure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will likely be the largest expense during your trip to Litchfield.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Litchfield. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've settled on your dates and duration, lock in the perfect Litchfield vacation package for you.

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