Cheshire Holidays

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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
Fully refundableReserve now, pay when you stay
The price is Rp1.609.857 per night from 5 Aug to 6 Aug
Rp1.609.857
Rp1.851.335 total
5 Aug - 6 Aug
includes taxes & fees
8.4/10 Very good! (843 reviews)
"We used the motel to break up our drive to Maine and to see family in the area. Great location with a nice bed for a good night's sleep. Room was dominated by the bed so not much room for anything else. It served it's purpose. Would stay again."

Reviewed on 13 Jul 2026

Cheshire Welcome Inn
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is Rp2.335.921 per night from 9 Aug to 10 Aug
Rp2.335.921
Rp2.686.309 total
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (2,208 reviews)
"All good"

Reviewed on 16 Jul 2026

New Haven 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 Rp2.051.079 per night from 20 Jul to 21 Jul
Rp2.051.079
Rp2.358.741 total
20 Jul - 21 Jul
includes taxes & fees
Best Western Executive Hotel Of New Haven - West Haven
See all 1,282 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.

Stay near popular Cheshire attractions

Roaring Brook Park

8.4/10 (12 reviews)
Connecticut's tallest single-drop waterfall cascades dramatically 80 feet through lush woodland. Hike the moderate one-mile loop trail in spring for the most impressive water flow after seasonal rains.
See properties

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.

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