Title: Holiday Rentals Chester from £208: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

[Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d6005399.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d6005399.Holidays-City-Breaks)

![An amazing keystone arch bridge!](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Chris Addams

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## Check prices for these dates

In two weeks

[20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Find holiday rentals that suit your style

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CONDO)

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE)

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN)

Chalets

[](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America&regionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CHALET)

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## Top Chester Hotel Reviews

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Room was reasonably comfortable and always nice to be looking out at the mountain. Staff is always pleasant and efficient. Very good value for the money."

[](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby. "

[](https://expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"loved "

[](https://expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg)

### Fairfield Inn & Suites Springfield Northampton/Amherst

10/10 Excellent

"Gorgeous room amazing stay"

[](https://expedia.co.uk/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Room was clean and nicely equipped with kitchen. Will return if the future. "

[](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg)

### Quality Inn & Suites Northampton - Amherst

10/10 Excellent

"Great room, very clean and welcoming, helpful staff. Breakfast was pretty good too!"

[](https://expedia.co.uk/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information)

![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg)

### Tru by Hilton Chicopee Springfield

10/10 Excellent

"Friendly clean accommodation were just what we needed. "

[](https://expedia.co.uk/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information)

![Hotel Northampton](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272_y.jpg)

### Hotel Northampton

10/10 Excellent

"The staff were amazing and the room was perfect. "

[](https://expedia.co.uk/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information)

![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg)

### D. Hotel Suites & Spa

10/10 Excellent

"Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back "

[](https://expedia.co.uk/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information)

## Find out more about Chester

**Everything you need to know about** **Chester** **holiday rentals**

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Chester holiday rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chester holiday rentals we have selected for you start as low as £208 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Chester rentals**

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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## Frequently asked questions

### Can I find a holiday rental in Chester?

### What are some of the best holiday rentals that Chester has to offer?

### What can I see and do in Chester?

### What are holiday rentals like in Chester?

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