Cheshire Holidays from £467

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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.
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2 out of 5
per person
19 Sept - 22 Sept
found 1 day ago
Return flight included
Manchester (MAN) to New Haven (HVN)
7.2/10 Good! (441 reviews)
Would have liked some fruit offered with breakfast, maybe dry cereal and milk. Main disappointment was that our non smoking room smelled significantly of old stale smoke, and makes our staying there again a nonstarter

Reviewed on 5 Aug 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
19 Sept - 22 Sept
found 1 day ago
Return flight included
Manchester (MAN) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
I love this property. But, very disappointed in the pool and lack of variety of food

Reviewed on 9 Aug 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
19 Sept - 22 Sept
found 1 day ago
Return flight included
Manchester (MAN) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on 1 May 2025

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
19 Sept - 22 Sept
found 1 day ago
Return flight included
Manchester (MAN) to New Haven (HVN)
7/10 Good! (888 reviews)
The pool wasn’t open, the room needed to be updated, bathroom outlet didn’t work, tv was static, I wouldn’t stay again.

Reviewed on 27 Jul 2025

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
19 Sept - 22 Sept
found 1 day ago
Return flight included
Manchester (MAN) to New Haven (HVN)
7.8/10 Good! (1,004 reviews)
This was my third stay at Pier Blue. Although it is an older property and could use a thorough update, I keep coming back for the location, the cleanliness and the reasonable rates. I must say, though, that there was one dirty hand towel on the shower curtain rod left from the previous guest. It was hidden by the shower curtain so I understand how it was overlooked. It was gross, though.

Reviewed on 8 Aug 2025

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

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 £91 per night from 7 Sept to 8 Sept
£91
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (1,000 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 3 Aug 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 £84 per night from 10 Aug to 11 Aug
£84
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (716 reviews)
"Comfortable, clean and convenient"

Reviewed on 7 Aug 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 £65 per night from 24 Aug to 25 Aug
£65
24 Aug - 25 Aug
includes taxes & fees
7.4/10 Good! (1,020 reviews)
"."

Reviewed on 6 Aug 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.
All Inclusive Holidays
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Family Friendly Holidays

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 £467. 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.