Cheshire Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to SAR 390 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Cheshire Vacation Packages

Cheshire Hotel Deals

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 SAR 416 per night from Apr 27 to Apr 28
SAR 416
SAR 479 total
includes taxes & fees
27 Apr - 28 Apr
8.2/10 Very Good! (1,000 reviews)
"Excellent"

Reviewed on 6 April 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 SAR 296 per night from Apr 20 to Apr 21
SAR 296
SAR 341 total
includes taxes & fees
20 Apr - 21 Apr
8.4/10 Very Good! (661 reviews)
"Very clean and very kind staff. They went above and beyond. Comfortable beds as well"

Reviewed on 6 April 2025

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 SAR 443 per night from Apr 27 to Apr 28
SAR 443
SAR 510 total
includes taxes & fees
27 Apr - 28 Apr
8.8/10 Excellent! (1,490 reviews)
"Easy checkin and parking."

Reviewed on 16 April 2025

New Haven Hotel
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.

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 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.

Discover the most popular places to visit in Cheshire