Cheshire Holidays

Book a Hotel + Flight or Car together to unlock savings

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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 2.585.720 ₫ per night from 26 Aug to 27 Aug
2.585.720 ₫
2.973.578 ₫ total
26 Aug - 27 Aug
includes taxes & fees
8.4/10 Very Good! (720 reviews)
"Overall good, affordable place to stay overnight. It was quiet and clean. Minus is general bad condition of property. Walls on a room need a painting and on some plaster is pilling off."

Reviewed on 23 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 2.220.398 ₫ per night from 26 Aug to 27 Aug
2.220.398 ₫
2.553.458 ₫ total
26 Aug - 27 Aug
includes taxes & fees
7.6/10 Good! (1,010 reviews)
"It was good"

Reviewed on 24 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 2.760.210 ₫ per night from 31 Aug to 1 Sept
2.760.210 ₫
3.174.242 ₫ total
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (1,304 reviews)
"Staff was very friendly and knowledgeable of the area."

Reviewed on 22 Aug 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,151 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.

Popular places to visit

Barker Character, Comic and Cartoon Museum

You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theatre scene in this romantic area.

Barker Character, Comic and Cartoon Museum

Cheshire Golf Course

Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theatre scene in this romantic area.

Cheshire Golf Course

Roaring Brook Park

Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theatre scene.

Roaring Brook Park

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.