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Chester Vacation Rentals

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Nov 7 - Nov 8
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Nov 8 - Nov 9
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Nov 14 - Nov 16

Vacation Rentals in Chester

Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Game room
Pet Friendly Riverfront Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥31,205
￥45,872 total
includes taxes & fees
Nov 9 - Nov 10
Pet Friendly Riverfront Home in Great Barrington
Dining
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.6 out of 10, Exceptional, (16)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
United States
Annie C.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (132)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
Outdoor pool
The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (207)
"Location was lovely. The house was peaceful and adorable."
United States
Kathy T.
The Clearing - Quiet - Close To Nature
Interior
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (227)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
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. "
United States
John Z.
The price is ￥58,943
￥114,552 total
includes taxes & fees
Nov 13 - Nov 14
Spacious 5-bedroom house in charming Lee with WiFi
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (70)
"Excellent location in Lee allowed us to visit many adjacent towns and attractions in the Berkshires. Very responsive host."
United States
Aditya J.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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. "
United States
Tamara S.
The price is ￥14,071
￥40,660 total
includes taxes & fees
Dec 1 - Dec 2
Charming Chicopee Getaway
Property grounds
Hadley Amherst Location.Explore the Valley Colleges!
Hadley Amherst Location.Explore the Valley Colleges!
10.0 out of 10, Exceptional, (132)
"Such a wonderful property and amazing host! A convenient location to the area as well as shopping and beautiful bike/walking trail!Thank you Colleen!"
United States
John M.
Hadley Amherst Location.Explore the Valley Colleges!
Terrace/patio
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
10.0 out of 10, Exceptional, (6)
"The place was great, sitting on a lake in a quiet neighborhood with plenty to do nearby. The host was quick with communication, not that there was anything we had to bother him with. Highly recommend!"
United States
Gary G.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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, (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 ￥27,531
￥42,370 total
includes taxes & fees
Nov 17 - Nov 18
The Creation Station is a cozy place so make yourself at home.
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, (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.
The price is ￥24,778
￥64,068 total
includes taxes & fees
Nov 10 - Nov 11
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior
Private Island - Largest Fresh Water Reservoir in Mass
Private Island - Largest Fresh Water Reservoir in Mass
8.6 out of 10, Excellent, (9)
"The house’s position on the water, being further out than all other surrounding homes, makes for beautiful views of the lake and all it activities. The sunrises are beautiful. Unfortunately when you don’t have proper running water and a toilet that flushes without having to put water in the tank almost every time, the experience is less than ideal. The host warned us of the toilet about 15 min before we arrived and never had the kitchen sink fixed in the 5 days we stayed. That was rather...
United States
Colleen W.
Private Island - Largest Fresh Water Reservoir in Mass
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds
Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the Berkshires
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 ￥30,590
￥56,099 total
includes taxes & fees
Nov 15 - Nov 16
Big farmhouse in the foothills of the Berkshires
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (229)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
United States
Donald G.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"Yes"
robert 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Springfield MA

Find out more about Chester

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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.