Cheshire Trips (flight + hotel)

Photo by Tai Bui

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Top hotels in Cheshire

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
64 Knotter Dr, Cheshire, CT
Fully refundable
The price is P6,104 per night from Sep 7 to Sep 8
P6,104
P7,020 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Other than some disappointment with breakfast, our stay was excellent. The manager was accomodating, and the front desk and housekeeping staff was excellent."

Reviewed on Aug 3, 2025

Holiday Inn Cheshire - Southington by IHG
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is P5,597 per night from Sep 10 to Sep 11
P5,597
P6,436 total
Sep 10 - Sep 11
includes taxes & fees
8.4/10 Very Good! (716 reviews)
"Comfortable, clean and convenient"

Reviewed on Aug 7, 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 P4,344 per night from Aug 26 to Aug 27
P4,344
P4,995 total
Aug 26 - Aug 27
includes taxes & fees
7.4/10 Good! (1,007 reviews)
Very pleasant
"Madeline at the front desk and all staff are very welcoming and professional. Hot breakfast is good and accomodations are clean and comfortable. GPS guided me into adjacent parking lot not affiliated with the hotel."

Reviewed on Aug 9, 2025

The Capitol Hotel
See all 1,142 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

Maplecroft Plaza Shopping Center

You can search for that perfect souvenir at Maplecroft Plaza Shopping Center during your visit to Cheshire. Experience the area's entertainment venues and theater scene.

Maplecroft Plaza Shopping Center

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.