Cheshire Holidays from £1,062

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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.

The Latest Cheshire Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Microtel Inn by Wyndham Albany Airport

Microtel Inn by Wyndham Albany Airport

2 out of 5
per person
1 Aug - 4 Aug
found 12 hours ago
Return direct flight included
London (LHR) to Albany (ALB)
7.8/10 Good! (1,024 reviews)
This was my second time staying at this property. I knew that I would have a night’s rest and be ready for the last hour and a half from my final destination. I had a lovely stay.

Reviewed on 22 Jun 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
per person
1 Aug - 4 Aug
found 12 hours ago
Return direct flight included
London (LHR) to Albany (ALB)
9.2/10 Wonderful! (32 reviews)
The spa was amazing right on the property of the hotel with a great experience

Reviewed on 15 Jun 2025

Hampton Inn Schenectady Downtown

Hampton Inn Schenectady Downtown

2.5 out of 5
Seward Place
per person
1 Aug - 4 Aug
found 12 hours ago
Return direct flight included
London (LHR) to Albany (ALB)
9/10 Wonderful! (915 reviews)
Clean room. Friendly staff.

Reviewed on 24 Jun 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
1 Aug - 4 Aug
found 12 hours ago
Return direct flight included
London (LHR) to Albany (ALB)
8.4/10 Very Good! (662 reviews)
Overall nice clean hotel . Need to update tvs so you can use streaming services. Need to update website about complimentary breakfast and late check out .

Reviewed on 1 Jun 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
1 Aug - 4 Aug
found 12 hours ago
Return direct flight included
London (LHR) to Albany (ALB)
7.4/10 Good! (1,000 reviews)
The original room given

Reviewed on 24 Jun 2025

Microtel Inn & Suites by Wyndham Amsterdam

Microtel Inn & Suites by Wyndham Amsterdam

2.5 out of 5
per person
1 Aug - 4 Aug
found 12 hours ago
Return direct flight included
London (LHR) to Albany (ALB)
9.4/10 Exceptional! (642 reviews)
Check-in was slow in front desk person was not very friendly. The hotel itself is very clean and nicely decorated. Breakfast was average at best. But overall not a bad place to stay.

Reviewed on 23 Jun 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

Our pick of the best Cheshire Hotel Deals

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."

Reviewed on 24 Jun 2025

Vacation Village in the Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business centre and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (659 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."

Reviewed on 21 Jun 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,004 reviews)
"I loved everything about this hotel! It was PERFECT! This is my favorite hotel!"

Reviewed on 23 Jun 2025

Best Western Plus Berkshire Hills Inn & Suites
See all 992 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

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

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 £1,062. 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.