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Chester Holiday Rentals

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Holiday Rentals in Chester

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
The price is AU$325
includes taxes & fees
24 Nov - 25 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
The price is AU$503
includes taxes & fees
30 Nov - 1 Dec
Home in the Woods

Peaceful Meadow Retreat

2.0 star property
Granby
10.0 out of 10, Exceptional, (16)
"The place is beautiful and very quiet and relaxing"
United States
Marian
The price is AU$312
includes taxes & fees
1 Dec - 2 Dec
Peaceful Meadow Retreat

Cozy Home in Holyoke with 3 bedrooms

Holyoke
9.8 out of 10, Exceptional, (11)
"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."
United States
Eric W.
The price is AU$507
includes taxes & fees
1 Dec - 2 Dec
Cozy Home in Holyoke with 3 bedrooms

The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.
10.0 out of 10, Exceptional, (71)
"This was our second time staying here and we had a great time!"
United States
Andy L.
The price is AU$439
includes taxes & fees
24 Nov - 25 Nov
The Creation Station is a cozy place so make yourself at home.

Townhouse with Pool Table - Renovated w/ King Bed

Chicopee
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."
United States
Matt G.
The price is AU$602
includes taxes & fees
24 Nov - 25 Nov
Townhouse with Pool Table - Renovated w/ King Bed

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$591
includes taxes & fees
1 Dec - 2 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"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."
United States
James D.
The price is AU$614
includes taxes & fees
1 Dec - 2 Dec
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Charming Chicopee Getaway

Chicopee
7.4 out of 10, Good, (3)
"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. "
United States
Tamara S.
The price is AU$551
includes taxes & fees
27 Nov - 28 Nov
Charming Chicopee Getaway

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale
9.8 out of 10, Exceptional, (33)
"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"
United States
Lindsey E.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AU$771
includes taxes & fees
24 Nov - 25 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (143)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
United States
Jon O.
The price is AU$575
includes taxes & fees
24 Nov - 25 Nov
Big farmhouse in the foothills of the Berkshires

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.2 out of 10, Wonderful, (5)
The price is AU$466
includes taxes & fees
24 Nov - 25 Nov
Pet Friendly Riverfront Home in Great Barrington

Welcoming 3-bedroom house- Gardner home

2.0 star property
Chicopee
The price is AU$528
includes taxes & fees
1 Dec - 2 Dec
Welcoming 3-bedroom house- Gardner home

Cozy Valley View Post & Beam Villa!

Whately
10.0 out of 10, Exceptional, (8)
"Thanks for a great stay"
United States
Andrea M.
The price is AU$1,998
includes taxes & fees
15 Dec - 16 Dec
Cozy Valley View Post & Beam Villa!

Cozy 2-bedroom apartment in Chicopee

Chicopee
The price is AU$318
includes taxes & fees
2 Dec - 3 Dec
Cozy 2-bedroom apartment in Chicopee

Charming Apt in 18th c Berkshire Farmhouse

Lanesborough
9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is AU$318
includes taxes & fees
24 Nov - 25 Nov
Charming Apt in 18th c Berkshire Farmhouse

Button's Modern Luxury Walkup Downtown Northampton

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"
United States
Meghan C.
Button's Modern Luxury Walkup Downtown Northampton
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, 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 favourite 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 depend 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 per night. Entering your travel dates in the search wizard might find you 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?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Chester is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like Berkshire Scenic Railway Museum, or get outside and enjoy nature at Pyramid Lake. Chester Town Hall and Skyline Trail 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.