Litchfield Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Litchfield

The Litchfield Inn
The Litchfield Inn
4 out of 5
432 Bantam Road, Litchfield, CT
Fully refundableReserve now, pay when you stay
The price is S$372 per night from 9 Jul to 10 Jul
S$372
9 Jul - 10 Jul
includes taxes & fees
9/10 Wonderful! (916 reviews)
"Beautiful, beautiful hotel and outstanding customer service and attention to detail. Not only was my room designed impeccably and clean, but there were free waters, snacks and freshly baked cookies available upon arrival. Their breakfast was outstanding (and free) and they had coffee, beverages and ..."

Reviewed on 14 Jun, 2025

The Litchfield Inn
The Abner Hotel
The Abner Hotel
3 out of 5
15 West St, Litchfield, CT
The price is S$346 per night from 29 Jul to 30 Jul
S$346
29 Jul - 30 Jul
includes taxes & fees
9.4/10 Exceptional! (18 reviews)
"Beautifully restored building- excellent service"

Reviewed on 27 Jun, 2025

The Abner Hotel
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
Fully refundableReserve now, pay when you stay
The price is S$130 per night from 3 Aug to 4 Aug
S$130
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"Nice place"

Reviewed on 5 Jul, 2025

Courtyard by Marriott Waterbury Downtown
See all 728 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 holiday 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 holiday to Litchfield costs.
What are the cheapest months to go to Litchfield?
If you're looking to score a cheap Litchfield holiday 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 holidays 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 neighbourhoods such as Litchfield Historic District and Milton Centre 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 holiday package to Litchfield?
Whether you're planning to explore attractions such as Litchfield Town Green and White Memorial Conservation Centre, or eager to experience its top-notch history and nature, a Litchfield holiday will leave you with lasting memories. Book your getaway with Expedia and discover why Litchfield is such a good holiday 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 holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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 travelling 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 accommodation 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 accommodation: Once you've settled on your dates and duration, lock in the perfect Litchfield holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.