Cheshire Vacations

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Find the Best Cheshire Vacation Packages

Cheshire Hotel Deals

Cheshire Welcome Inn

Cheshire Welcome Inn

1106 S Main St. Cheshire CT
Fully refundableReserve now, pay when you stay
NT$2,819
NT$3,242 total
Sep 8 - Sep 9
includes taxes & fees
8.4/10 Very Good! (875 reviews)
"Nice, clean, nice staff!"

Reviewed on 2026/9/6

Cheshire Welcome Inn
The Capitol Hotel

The Capitol Hotel

440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
NT$3,200
NT$3,680 total
Sep 10 - Sep 11
includes taxes & fees
7.4/10 Good! (1,516 reviews)
"Moderately priced room in downtown Hartford. The room was clean and comfortable. There was no hotel courtesy parking. Lot in rear was $18.00 per night. The hotel also required a $100.00 deposit upon check in. Hopefully not charged to my cc as the room was left as we found it upon check out."

Reviewed on 2026/9/4

The Capitol Hotel
New Haven Hotel

New Haven Hotel

229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
NT$4,129
NT$4,749 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (2,315 reviews)
"The staff didn’t tell us the parking is at cost and charge us directly after we check out"

Reviewed on 2026/9/6

New Haven Hotel
See all 1,293 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.
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Barker Character, Comic and Cartoon Museum

7.0/10 (12 reviews)
Step back in time at this treasure trove of over 80,000 character toys and memorabilia from 1873 to today. Explore meticulously arranged exhibits that evoke nostalgia across generations of American pop culture.
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Cheshire Hollow Farm

8.4/10 (15 reviews)
This 94-acre working farm invites visitors to interact with pygmy goats, miniature horses, and other friendly animals. Experience nature hikes, scavenger hunts, and seasonal activities like pumpkin picking and hayrides.
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Maplecroft Plaza Shopping Center

8.6/10 (14 reviews)
Maplecroft Plaza serves local Cheshire residents with essential retail shops in a convenient setting. Browse the diverse stores during weekday mornings when the atmosphere is most relaxed and parking is plentiful.
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Lock 12 Historical Park

Discover America's canal history at Lock 12 Historical Park, home to the only intact lock from the 1828 Farmington Canal. Walk the heritage trail after exploring the lock-keeper's house and canal artifacts.
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Drazen Orchards

7.8/10 (10 reviews)
This family-owned orchard invites you to pick seasonal fruits straight from the trees since 1951. Savor the harvest experience with weekend wagon rides and farm-fresh treats at their charming stand.
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Bartlem Park

8.6/10 (13 reviews)
This vibrant community hub offers sports fields, a playground, and the Cheshire Community Pool for active pursuits. Enjoy a family picnic in the pavilion area or time your visit for the annual Fall Festival in September.
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Quinnipiac Recreation Area

8.6/10 (14 reviews)
This 59-acre community park offers well-maintained fields for soccer, lacrosse, and in-line skating. Families can enjoy the pavilion's picnic areas while watching local sports events unfold.
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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.

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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.