Cheshire Holidays from £710

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Your Cheshire Holiday

When an adventure in the city is calling your name, answer it with a Cheshire holiday package. With all your travel needs taken care of before you go, all you have to do here is focus on enjoying yourself. Like to explore your new surroundings? Mount Greylock, Mount Greylock State Reservation and East Hoosac Quaker Meetinghouse are just a few of the best places to visit during a trip to Cheshire. Don't delay visiting this destination any longer. The ultimate Cheshire holiday is a few quick clicks away with Expedia.

Top Cheshire Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Clocktower Hotel at Century House, Ascend Hotel Collection

The Clocktower Hotel at Century House, Ascend Hotel Collection

2.5 out of 5
per person
24 Sept - 30 Sept
found 1 day ago
Return flight included
London (LGW) to Albany (ALB)
8.2/10 Very Good! (1,013 reviews)
Clean, comfortable beds, but lots of plumbing noise and leaks in ceiling.

Reviewed on 11 Aug 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
24 Sept - 30 Sept
found 1 day ago
Return flight included
London (LGW) to Albany (ALB)
8/10 Very Good! (1,159 reviews)
Could use an update. Getting rather dated.

Reviewed on 11 Aug 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
24 Sept - 30 Sept
found 1 day ago
Return flight included
London (LGW) to Albany (ALB)
8.4/10 Very Good! (673 reviews)
Comfortable and clean.

Reviewed on 6 Aug 2025

La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
per person
24 Sept - 30 Sept
found 1 day ago
Return flight included
London (LGW) to Albany (ALB)
7.4/10 Good! (1,000 reviews)
No hot water in the sinks, rust in tub area, keys didn’t work properly

Reviewed on 4 Aug 2025

Renaissance Albany Hotel

Renaissance Albany Hotel

3.5 out of 5
Downtown Albany
per person
24 Sept - 30 Sept
found 1 day ago
Return flight included
London (LGW) to Albany (ALB)
9.2/10 Wonderful! (946 reviews)
Th property was good. We just didn’t like to area.

Reviewed on 7 Aug 2025

Cheshire Essential Information

Language
English
Currency
U.S dollars
Population
510
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Jiminy Peak Mountain Resort, Bousquet Ski Area and Natural Bridge State Park

Top hotels in Cheshire

Harbour House Inn

Harbour House Inn

3.5 out of 5
725 North State Road, Cheshire, MA
The price is £185 per night from 18 Aug to 19 Aug
£185
18 Aug - 19 Aug
includes taxes & fees
9.6/10 Exceptional! (37 reviews)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!!"

Reviewed on 4 Jul 2025

Harbour House Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is £98 per night from 27 Aug to 28 Aug
£98
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,938 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."

Reviewed on 10 Aug 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (554 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."

Reviewed on 11 Aug 2025

Get rates
Berkshire Mountain Lodge
See all 999 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?
Be ready to book, because a getaway to Cheshire starts from an enticing £710. When you bundle your flights, hotels and car rentals into a package, you'll score the lowest prices.
If I'm not able to travel, can I cancel my Cheshire travel package?
You sure can, and we're here to help. You may be able to cancel or change your Cheshire travel package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, visit our Customer Service Portal for further information.
How do I get a cheap travel package to Cheshire?
Just think of all the fun things you could do in Cheshire with a wad of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a Cheshire travel package. You have plenty of choice with Expedia too. In fact, you can take your pick of more than 550 airlines and 1,000,000 hotels globally. Whether you're heading off with the family or travelling solo, planning a trip to Cheshire is better with a package.
Does Expedia offer Book Now, Pay Later Cheshire holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that suits best during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can book that well-deserved holiday now.
  • Pay in instalments holidays: If you'd like to pay off your getaway in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you come across an awesome deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Cheshire?
There's plenty to do in Cheshire, so spend your nights close to its top sights and allow yourself more time sightseeing. Mount Greylock State Reservation Visitor Centre is one spot to put on your must-see list.
What are the top hotels in Cheshire?
Reserve a room at Boston Park Plaza. It's one of this area's most popular hotels. Another great option in Cheshire is Embassy Suites Boston Logan Airport.
How far in advance should I book my Cheshire holiday?
It can be tricky to know when the best time is to book your Cheshire trip. But generally the earlier you book, the lower the prices. In some cases, you can book your flights and hotels up to a year before departure. If you're considering a last-minute getaway, no need to panic! There are unbeatable deals posted on Expedia every day.
What does an Expedia Cheshire travel package include?
From flights and hotels to car rentals, Expedia can help you shape a Cheshire package that fits you. Holidaying for a week or two? Give some thought to a hotel, rental car and flight bundle. If you can only manage a quick getaway, an airfare and hotel deal could suit you better. Activities can also be added once you've made your booking. Our packages make it simple to plan and save.
What should I know before booking a Cheshire travel package?
Discover deals that match your budget with an Expedia package. Hotels, airfares, rental cars — we're a one-stop shop for all of them. You'll save precious cash just by bundling your bookings. Whether you're taking off on an adventure in the snow or sipping cocktails on a beach, your dream getaway is just a few clicks away.
Can I choose my airline with a Cheshire Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our travel packages give you the freedom to pick from available flights, hotels and activities that suit you.

* 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.