Cheshire Holidays

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Your Cheshire Holiday

Book a Cheshire holiday package and get set for a fabulous getaway. With a reputation for its rich history and spectacular views, there's plenty to keep you on the go in this fascinating city. Every trip to Cheshire needs a well-crafted itinerary. Fill yours with famous sights like Toyota Oakdale Theatre, Choate Rosemary Hall and Sleeping Giant State Park. Whatever your travel plans or the size of your budget, putting together a tailored Cheshire holiday is easy with Expedia.

Cheshire Holiday

Cheshire Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
29,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Lake Compounce, Toyota Oakdale Theatre and Powder Ridge Mountain Park and Resort

Our pick of the best Cheshire Hotel Deals

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is AU$174 per night from 21 Aug to 22 Aug
AU$174
21 Aug - 22 Aug
includes taxes & fees
8.4/10 Very Good! (717 reviews)
"You can tell this hotel was an older one that had been renovated, but it was by far one of the cleanest ones I have stayed in ever. The beds were as comfortable as other high dollar chain hotels. Staff was exceptionally friendly, and the grounds were impeccable. Bring your own soaps and shampoos ..."

Reviewed on 18 Aug. 2025

Cheshire Welcome Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 21 Aug to 22 Aug
AU$149
21 Aug - 22 Aug
includes taxes & fees
7.4/10 Good! (1,022 reviews)
"Thank you for having us and our dogs. Nice spot to be."

Reviewed on 18 Aug. 2025

The Capitol 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 AU$185 per night from 24 Aug to 25 Aug
AU$185
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,288 reviews)
"Great location with multiple food options nearby."

Reviewed on 18 Aug. 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,144 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.