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Chester Vacation Rentals

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Vacation Rentals in Chester

Cozy 2-bedroom apartment in Chicopee

Chicopee
$151 nightly
The price is $172
Dec 3 - Dec 4
Total with taxes and fees
Cozy 2-bedroom apartment in Chicopee

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
$121 nightly
The price is $136
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow

Charming Chicopee Getaway

Chicopee
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. "
United States
Tamara S.
$229 nightly
The price is $267
Dec 9 - Dec 10
Total with taxes and fees
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.
$288 nightly
The price is $322
Nov 12 - Nov 13
Total with taxes and fees
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.
$158 nightly
The price is $179
Nov 16 - Nov 17
Total with taxes and fees
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.
$188 nightly
The price is $206
Nov 12 - Nov 13
Total with taxes and fees
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.
$339 nightly
The price is $385
Nov 13 - Nov 14
Total with taxes and fees
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.
$440 nightly
The price is $492
Nov 13 - Nov 14
Total with taxes and fees
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.
$351 nightly
The price is $392
Nov 12 - Nov 13
Total with taxes and fees
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.
$202 nightly
The price is $226
Nov 12 - Nov 13
Total with taxes and fees
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.
$344 nightly
The price is $364
Nov 14 - Nov 15
Total with taxes and fees
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.
$253 nightly
The price is $283
Nov 13 - Nov 14
Total with taxes and fees
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.
$540 nightly
The price is $603
Nov 12 - Nov 13
Total with taxes and fees
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.
$199 nightly
The price is $219
Nov 12 - Nov 13
Total with taxes and fees
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.
$666 nightly
The price is $743
Nov 17 - Nov 18
Total with taxes and fees
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.
$304 nightly
The price is $321
Nov 12 - Nov 13
Total with taxes and fees
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, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Nov 12 - Nov 13
Total with taxes and fees
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.
$541 nightly
The price is $604
Nov 12 - Nov 13
Total with taxes and fees
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.
$345 nightly
The price is $385
Nov 30 - Dec 1
Total with taxes and fees
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
$188 nightly
The price is $206
Nov 12 - Nov 13
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation 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 vacation.

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 vacation rental in Chester?

Yes, you can find vacation rentals close to well known sights in Chester, or you can select a more secluded option if you want a relaxing place to 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 vacation rentals that Chester has to offer?

Pet Friendly Riverfront Home in Great Barrington: You might want to consider this vacation home rental near Chester, which 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 vacation with amenities like 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 larger area.

What are vacation rentals like in Chester?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Chester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.