Cheshire 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

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Top hotels in Cheshire

Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
The price is S$131 per night from 10 Jul to 11 Jul
S$131
10 Jul - 11 Jul
includes taxes & fees
8.4/10 Very Good! (701 reviews)
"Reasonably priced, clean, comfortable bed"

Reviewed on 6 Jul, 2025

Cheshire Welcome Inn
Holiday Inn Cheshire - Southington by IHG
Holiday Inn Cheshire - Southington by IHG
3 out of 5
64 Knotter Dr, Cheshire, CT
Fully refundable
The price is S$158 per night from 27 Jul to 28 Jul
S$158
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Great easy stay I come here a lot when I’m in the area k just wish people would stop smoking"

Reviewed on 4 Jul, 2025

Holiday Inn Cheshire - Southington by IHG
The Capitol Hotel
The Capitol Hotel
3 out of 5
440 Asylum St, Hartford, CT
The price is S$149 per night from 16 Jul to 17 Jul
S$149
16 Jul - 17 Jul
includes taxes & fees
7.4/10 Good! (1,008 reviews)
"Staff where personable."

Reviewed on 6 Jul, 2025

The Capitol Hotel
See all 1,143 properties in Cheshire
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 Cheshire holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday to Cheshire costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Cheshire?
If you're hoping to book a cheap Cheshire holiday package, consider planning a trip in December, January and February. You'll generally find better rates on flights and hotels during these months --- ideal for a budget-friendly break.
How many days is enough for Cheshire?
Allow at least 2 days for your Cheshire holiday to discover all that makes this destination unique. Stroll around key neighbourhoods, including Milldale and Cheshire Historic District. Then head to the major sights such as Cheshire Hollow Farm and Bartlem Park. With a well-organised itinerary, you can keep busy with room for some me-time too. Want to travel beyond Cheshire? Consider an excursion or two.
Is it worth booking a holiday package to Cheshire?
From top attractions such as Cheshire Golf Course and Cheshire Hollow Farm to its excellent hiking, a Cheshire holiday is sure to exceed your expectations. With so much to do and see, it's time to find out for yourself why Cheshire is such a good holiday destination.
How to find the best Cheshire package deals?
Landing a cheap Cheshire package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most economical Cheshire package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Cheshire 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 typically land a better deal than booking each component individually. And you'll still have the freedom to create a personalised Cheshire holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Cheshire?
Secure incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Cheshire adventure.
How to plan a trip to Cheshire?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Cheshire.
  2. Plan your budget wisely: Besides the cost of your hotel, you should factor in other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could arise during your trip to Cheshire.
  3. Decide your trip length: Consider how much time you want to spend discovering Cheshire. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalised Cheshire holiday package.

* 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.