Cheshire Vacations

Book a Hotel + Flight or Car together to unlock savings

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Find the Best Cheshire Vacation Packages

Cheshire Hotel Deals

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is NT$2,999 per night from Aug 26 to Aug 27
NT$2,999
NT$3,449 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (719 reviews)
"The professionalism and the courtesy was excellent. The staff is friendly, welcoming and professional."

Reviewed on 2025/8/18

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 NT$2,575 per night from Aug 26 to Aug 27
NT$2,575
NT$2,962 total
Aug 26 - Aug 27
includes taxes & fees
7.6/10 Good! (1,007 reviews)
"We needed a place to rest our head for the night"

Reviewed on 2025/8/21

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 NT$3,202 per night from Aug 31 to Sep 1
NT$3,202
NT$3,682 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,304 reviews)
"Staff was very friendly and knowledgeable of the area."

Reviewed on 2025/8/22

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.

Discover the most popular places to visit in Cheshire

Cheshire Hollow Farm

Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.

Cheshire Hollow Farm

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 theater scene in this romantic area.

Barker Character, Comic and Cartoon Museum

Quinnipiac Recreation Area

Explore the great outdoors at Quinnipiac Recreation Area, a lovely green space in Cheshire. Experience the entertainment venues and theater scene in this romantic area.

Quinnipiac Recreation Area

Frequently asked questions

How much does a Cheshire vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation 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 vacation to discover all that makes this destination unique. Stroll around key neighborhoods, including Milldale and Cheshire Historic District. Then head to the major sights such as Cheshire Hollow Farm and Bartlem Park. With a well-organized 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 vacation package to Cheshire?
From top attractions such as Cheshire Golf Course and Cheshire Hollow Farm to its excellent hiking, a Cheshire vacation 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 vacation 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," "Traveler 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 traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Cheshire vacation as a package?
Expedia vacation 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 personalized Cheshire vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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, favorite 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 personalized Cheshire vacation package.

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