Cheshire Holidays from £879
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Your Cheshire Holiday
There's plenty to love about Cheshire, from its rich history to its spectacular views and beyond. When you're ready to say hello to this lively city, our Cheshire holiday packages will be just the ticket. Any trip to Cheshire needs a well-crafted itinerary. Fill yours with leading attractions like Toyota Oakdale Theatre, Choate Rosemary Hall and Mount Southington Ski Area. Expedia will help you escape your daily routine. Tailor your holiday to Cheshire to suit your style of travel, whatever that may look like.
Top Cheshire Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hyatus Luxury Residences City Crossing
The Hill
£1,036
per person
5 Dec - 12 Dec
found 1 day ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on 10 Aug 2026
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
£1,013
per person
5 Dec - 12 Dec
found 1 day ago
Return direct flight included
Birmingham (BHX) to New Haven (HVN)
9.6/10 Exceptional! (88 reviews)
Excellent value — a very thoughtfully decorated and well-maintained apartment, effective air conditioning, blackout curtains in every room — really helped the vacation to feel like a “treat”!
I did feel their app / web portal had “quite a lot” baked in it which could feel intimidating at first — vs. a “easy button” version at the top for simple functions like lock/unlock door — but would absolutely consider other Hyatus properties in the future!
Reviewed on 18 Sept 2026
Cheshire Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 29,400 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Lake Compounce, Toyota Presents Oakdale Theatre and Powder Ridge Mountain Park and Resort |
Top hotels in Cheshire
Cheshire Welcome Inn
1106 S Main St. Cheshire CT
Fully refundableReserve now, pay when you stay
£77
29 Sept - 30 Sept
includes taxes & fees
8.4/10 Very good! (882 reviews)
"Best choice around for the price. Very clean and good location."
Reviewed on 27 Sept 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
£88
28 Sept - 29 Sept
includes taxes & fees
7.4/10 Good! (1,547 reviews)
"Walking distance to People's Arena."
Reviewed on 27 Sept 2026
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
£104
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (2,351 reviews)
"Sour smelling bathroom, moldy showers"
Reviewed on 27 Sept 2026
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.
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.
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.
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.
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 artefacts.
Drazen Orchards
7.8/10 (10 reviews)
This family-owned orchard invites you to pick seasonal fruits straight from the trees since 1951. Savour the harvest experience with weekend wagon rides and farm-fresh treats at their charming stand.
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 Autumn Festival in September.
Quinnipiac Recreation Area
8.6/10 (14 reviews)
This 59-acre community park offers well-maintained fields for football, lacrosse, and in-line skating. Families can enjoy the pavilion's picnic areas while watching local sports events unfold.
Frequently asked questions
How much does a Cheshire travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Cheshire from just £879. And the more you bundle, the more money you save. Your dream escape has never been more affordable.
If I'm not able to travel, can I cancel my Cheshire travel package?
If your holiday plans in Cheshire have been upended, it's good to know that you can cancel your booking. If you made your booking in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a fee. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Cheshire?
Bundle your hotel and flight bookings, throw in extras such as a rental car or activities, and save with a Cheshire travel package. You won't just enjoy superb discounts on your escape — you'll have a world of choice too. When you book through Expedia, you can select from more than 550 air carriers and 1,000,000 properties globally. Your next affordable adventure begins right here, right now!
Does Expedia offer Book Now, Pay Later Cheshire holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a dream getaway without drying up your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:
- Pay monthly holidays: Klarna offers convenient monthly payment plans that work for all budget sizes, so you can lock in that well-earned holiday sooner.
- Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.
Where should I stay in Cheshire?
With popular attractions such as Cheshire Golf Course and Cheshire Hollow Farm in this area, look for a hotel situated near either of them. Bartlem Park is another Cheshire sight that lures the crowds.
What are the top hotels in Cheshire?
Hilton Stamford Hotel & Executive Meeting Centre and Howard Johnson by Wyndham Mystic are two of the most sought-after properties in Cheshire. Why not look up the amenities and rates at each and then make up your mind?
How far in advance should I book my Cheshire holiday?
Smart travellers often book early. You can generally compare international fares on Expedia up to a year before your flight. If you're purchasing tickets last minute, don't stress. Cheap prices sometimes occur in the last weeks before departure.
What does an Expedia Cheshire travel package include?
It all boils down to what type of getaway you're contemplating. Cheshire travel deals can include flights, hotels and car rentals. You can mix and match to find the bundle that suits your needs. You can also add on activities and experiences after you've booked to land even bigger discounts.
What should I know before booking a Cheshire travel package?
Bundling your bookings into a Cheshire travel package is the easiest way to organise your trip. Not only that, you'll save when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Cheshire Expedia travel package?
Yes, definitely. Expedia has more than 550 partner airlines to choose from around the globe. With all that choice at your fingertips, finding the perfect carrier to get you to Cheshire will be easy.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
