Photo by Elizabeth Massa Peroulakis

Chester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
This weekend
Oct 17 - Oct 19
Next weekend
Oct 24 - Oct 26

Vacation Rentals in Chester

Fridge, microwave, oven, stovetop
Charming Chicopee Getaway
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. "
Tamara S.
The price is ￥15,026
￥41,862 total
includes taxes & fees
Nov 11 - Nov 12
Charming Chicopee Getaway
Terrace/patio
Peaceful Meadow Retreat
Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (13)
"Quite and very clean"
Craig M.
The price is ￥16,769
￥30,930 total
includes taxes & fees
Oct 20 - Oct 21
Peaceful Meadow Retreat
Terrace/patio
Cozy Home in Holyoke with 3 bedrooms
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."
Eric W.
The price is ￥19,534
￥48,675 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Home in Holyoke with 3 bedrooms
Property grounds
The Creation Station is a cozy place so make yourself at home.
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!"
Andy L.
The price is ￥27,047
￥42,129 total
includes taxes & fees
Oct 22 - Oct 23
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop
Townhouse with Pool Table - Renovated w/ King Bed
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."
Matt G.
The price is ￥27,047
￥56,767 total
includes taxes & fees
Oct 20 - Oct 21
Townhouse with Pool Table - Renovated w/ King Bed
Private kitchen
Humble home with free breakfast
Humble home with free breakfast
7.0 out of 10, Good, (2)
The price is ￥20,675
￥49,090 total
includes taxes & fees
Nov 3 - Nov 4
Humble home with free breakfast
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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."
Sharon K.
The price is ￥24,342
￥59,919 total
includes taxes & fees
Oct 28 - Oct 29
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
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."
James D.
The price is ￥24,072
￥59,113 total
includes taxes & fees
Oct 27 - Oct 28
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Terrace/patio
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
2.0 star property
The price is ￥29,301
￥42,249 total
includes taxes & fees
Oct 26 - Oct 27
Charming 2-bedroom house in beautiful countryside of Cummington, Ma
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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"
Lindsey E.
The price is ￥28,399
￥66,969 total
includes taxes & fees
Oct 20 - Oct 21
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Smart TV, fireplace, printers
Cozy Valley View Post & Beam Villa!
Cozy Valley View Post & Beam Villa!
10.0 out of 10, Exceptional, (6)
"Thanks for a great stay"
Andrea M.
The price is ￥90,156
￥113,628 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Valley View Post & Beam Villa!
Oven, stovetop, dishwasher
Button's Modern Luxury Walkup Downtown Northampton
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"
Meghan C.
The price is ￥37,565
￥75,696 total
includes taxes & fees
Nov 3 - Nov 4
Button's Modern Luxury Walkup Downtown Northampton
Property grounds
Big farmhouse in the foothills of the Berkshires
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!"
Jon O.
The price is ￥30,052
￥53,683 total
includes taxes & fees
Oct 24 - Oct 25
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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."
Sarah D.
The price is ￥28,534
￥70,475 total
includes taxes & fees
Oct 29 - Oct 30
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop
Historic downtown house. Unscented products and sustainability practices.
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 "
Camilo W.
The price is ￥47,332
￥89,962 total
includes taxes & fees
Oct 20 - Oct 21
Historic downtown house. Unscented products and sustainability practices.
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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!"
Ann C.
The price is ￥40,435
￥72,861 total
includes taxes & fees
Oct 20 - Oct 21
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
Dale G.
The price is ￥45,078
￥62,773 total
includes taxes & fees
Nov 3 - Nov 4
Bungalow in the Berkshires
Game room
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
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. "
Cristine C.
The price is ￥33,809
￥47,667 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
John Z.
The price is ￥64,236
￥120,426 total
includes taxes & fees
Oct 24 - Oct 25
Spacious 5-bedroom house in charming Lee with WiFi
Property grounds
Charming 3-bedroom Modern cottage with lakeside views
Charming 3-bedroom Modern cottage with lakeside views
2.0 star property
The price is ￥135,234
￥223,361 total
includes taxes & fees
Oct 20 - Oct 21
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Room adequate for a night stay. Breakfast service was odd. A maintenance person gave us one napkin & silverware service for 2 people. Hard boiled eggs brought still in the shell w/no way to rinse off the shells once peeled. "
ELIZABETH 1-night trip
Posted 1 day ago
Berkshires Untold

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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?

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water": You might want to consider this vacation home rental near Chester, which is located on a river and offers a fireplace, laundry facilities, and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a stovetop and a microwave can make your vacation 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 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.