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Holiday Rentals in Chester

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Holiday Rentals in Chester

Charming Chicopee Getaway
10.0 out of 10, Exceptional, (1)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
The price is €246
includes taxes & fees
11 Nov - 12 Nov
Charming Chicopee Getaway
Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (13)
"Quite and very clean"
The price is €182
includes taxes & fees
20 Oct - 21 Oct
Peaceful Meadow Retreat
Cozy Home in Holyoke with 3 bedrooms
9.6 out of 10, Exceptional, (9)
"What a great house and such gracious hosts!The location is just minutes from Mount Holyoke College which was perfect for our trip Super clean and well maintained house. I highly recommend staying here."
The price is €286
includes taxes & fees
13 Nov - 14 Nov
Cozy Home in Holyoke with 3 bedrooms
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (69)
"This was our second time staying here and we had a great time!"
The price is €248
includes taxes & fees
16 Oct - 17 Oct
The Creation Station is a cozy place so make yourself at home.
Townhouse with Pool Table - Renovated w/ King Bed
10.0 out of 10, Exceptional, (11)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
The price is €333
includes taxes & fees
16 Oct - 17 Oct
Townhouse with Pool Table - Renovated w/ King Bed
Humble home with free breakfast
7.0 out of 10, Good, (2)
The price is €287
includes taxes & fees
3 Nov - 4 Nov
Humble home with free breakfast
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is €353
includes taxes & fees
12 Nov - 13 Nov
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
The price is €347
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is €257
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (32)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Cozy Valley View Post & Beam Villa!
10.0 out of 10, Exceptional, (6)
"Thanks for a great stay"
The price is €669
includes taxes & fees
20 Oct - 21 Oct
Cozy Valley View Post & Beam Villa!
Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (1)
"This was the best rental apartment I've stayed at and definitely the cleanest. Check-in is easy, the pictures are accurate, the kitchen and bathroom are great, and the location in downtown Northampton is super walkable to cafes, shops, Smith, etc. If I'm ever back anywhere near the area, I will definitely try to stay there again. 10/10"
The price is €444
includes taxes & fees
3 Nov - 4 Nov
Button's Modern Luxury Walkup Downtown Northampton
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is €324
includes taxes & fees
19 Oct - 20 Oct
Big farmhouse in the foothills of the Berkshires
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
The price is €389
includes taxes & fees
16 Oct - 17 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Historic downtown house. Unscented products and sustainability practices.
10.0 out of 10, Exceptional, (5)
"It’s a beautiful home that worked for our stay as a family "
The price is €538
includes taxes & fees
27 Oct - 28 Oct
Historic downtown house. Unscented products and sustainability practices.
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is €432
includes taxes & fees
16 Oct - 17 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
The price is €365
includes taxes & fees
16 Oct - 17 Oct
Bungalow in the Berkshires
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
The price is €280
includes taxes & fees
2 Nov - 3 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Spacious 5-bedroom house in charming Lee with WiFi
The price is €734
includes taxes & fees
26 Oct - 27 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Charming 3-bedroom Modern cottage with lakeside views
2.0 star property
The price is €1,314
includes taxes & fees
18 Oct - 19 Oct
Charming 3-bedroom Modern cottage with lakeside views
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.
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Top Chester Hotel Reviews

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, cottages, apart-hotels, cabins, 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 €246 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. 

Frequently asked questions

Can I find a holiday rental in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfalls and shopping. Make sure you have time to check out the riverfront and restaurants during your trip.

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

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Chester offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like The Bookstore, or get outside and enjoy nature at Glendale Falls. Chester Town Hall and Pyramid Lake are a couple of places you'll find in the wider area.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family gatherings.