Photo by Elizabeth Massa Peroulakis

Chester Holiday Rentals

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Holiday Rentals in Chester

Cozy 2-bedroom apartment in Chicopee

Chicopee
The price is NZ$359
includes taxes & fees
13 Nov - 14 Nov
Cozy 2-bedroom apartment in Chicopee

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The Ponds at Foxhollow

Charming Chicopee Getaway

Chicopee
6.0 out of 10, (2)
"The apartment didn't look anything like the pictures. It was dingy and had a smell to it that we couldn't tolerate and that lingered in our nostrils for hours after we left. The kitchen area was unusable -- what passed for a table was at the same level as the chair seats, which made it impossible to use. Finally, we had to move a big trash bag full of trash out of the way before even being able to get in the door. We left within minutes after arriving and went to a hotel. "
United States
Kenneth M.
The price is NZ$460
includes taxes & fees
17 Nov - 18 Nov
Charming Chicopee Getaway

Cozy Home in Holyoke with 3 bedrooms

Holyoke
9.6 out of 10, Exceptional, (10)
"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "
United States
Carrie M.
The price is NZ$573
includes taxes & fees
4 Dec - 5 Dec
Cozy Home in Holyoke with 3 bedrooms

Peaceful Meadow Retreat

2.0 star property
Granby
10.0 out of 10, Exceptional, (15)
" Wonderful property, quiet and clean. Beautiful surroundings!"
United States
Craig M.
The price is NZ$316
includes taxes & fees
16 Nov - 17 Nov
Peaceful Meadow Retreat

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Very cute! Perfect place for a weekend in the Berkshires"
United States
Melissa P.
The price is NZ$365
includes taxes & fees
16 Nov - 17 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse

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 NZ$680
includes taxes & fees
13 Nov - 14 Nov
Townhouse with Pool Table - Renovated w/ King Bed

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 NZ$869
includes taxes & fees
14 Nov - 15 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 NZ$694
includes taxes & fees
13 Nov - 14 Nov
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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

Easthampton Ma.
10.0 out of 10, Exceptional, (70)
"A very short but a really fun stay. Great location to just relax and get away from it all."
United States
Naseem P.
The price is NZ$400
includes taxes & fees
13 Nov - 14 Nov
The Creation Station is a cozy place so make yourself at home.

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (141)
"We enjoyed our stay in this beautiful old farmhouse. Plenty of room for everyone and kitchen and linens were fully stocked."
United States
Nicole K.
The price is NZ$538
includes taxes & fees
17 Nov - 18 Nov
Big farmhouse in the foothills of the Berkshires

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$526
includes taxes & fees
13 Nov - 14 Nov
Pet Friendly Riverfront Home in Great Barrington

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.
The price is NZ$1,074
includes taxes & fees
23 Nov - 24 Nov
Button's Modern Luxury Walkup Downtown Northampton

Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough
9.0 out of 10, Wonderful, (22)
"Very nice. Attending a wedding in the area and really needed a place to get dressed and return to sleep. This fit the bill perfectly. Clean and comfortable we enjoyed our visit. Need to come back and visit the many sites in the area."
United States
Margaret K.
The price is NZ$389
includes taxes & fees
13 Nov - 14 Nov
Bright Boho Apt in 18th c Berkshire Farmhouse

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is NZ$1,314
includes taxes & fees
19 Nov - 20 Nov
Spacious 5-bedroom house in charming Lee with WiFi

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"Jessica's spot is adorable and tidy, at the end of a quiet, shady lane, with lots of peace and privacy. It was a hot, muggy weekend but there were 2 window units and extra fans to keep us comfortable. The house is well-appointed—we had a busy schedule and were sad we didn't have a chance to use the lovely outdoor fire pit area. Good communication after a minor mixup. Would definitely stay again!"
United States
Jennifer F.
The price is NZ$568
includes taxes & fees
13 Nov - 14 Nov
Home in the Woods

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

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
The price is NZ$667
includes taxes & fees
17 Nov - 18 Nov
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Historic downtown house. Unscented products and sustainability practices.

Northampton
10.0 out of 10, Exceptional, (6)
"It’s a beautiful home that worked for our stay as a family "
United States
Camilo W.
The price is NZ$1,076
includes taxes & fees
17 Nov - 18 Nov
Historic downtown house. Unscented products and sustainability practices.

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
The price is NZ$681
includes taxes & fees
30 Nov - 1 Dec
Bungalow in the Berkshires

Charming Apt in 18th c Berkshire Farmhouse

Lanesborough
9.4 out of 10, Exceptional, (39)
"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 NZ$367
includes taxes & fees
13 Nov - 14 Nov
Charming Apt in 18th c Berkshire Farmhouse
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 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 NZ$400 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?

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 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.