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Chester Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chester Vacation Homes

Peace and quiet on the lake
Enjoy the airy feel of this room with a high ceiling and skylight, featuring a balcony with a railing.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"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! "
Peace and quiet on the lake
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Enjoy meals in this elegant dining area with a central table and six chairs, surrounded by high ceilings and large windows.

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (127)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Escape to a serene lakeside retreat surrounded by lush greenery and vibrant flowers.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (14)
"Very friendly hosts, great location. "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Deluxe Queen Room with 2 Queen Beds
Guest rooms lead to a covered walkway with a tiled floor.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (3)
"Pool is caving in with pool cover partly pulled away. Gate to access pool area was unlocked. Hazard for children. Staff is not onsite. Room was clean, but sheets had stains. Used bar of soap left on bathroom sink. "
The price is CA $136
CA $183 total
includes taxes & fees
Sep 1 - Sep 2
Deluxe Queen Room with 2 Queen Beds
Big farmhouse in the foothills of the Berkshires
Surrounded by lush greenery, this serene property features a beautifully maintained front yard with flowering shrubs and a neatly trimmed lawn.

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (139)
"It is a quiet and beautiful home. The surrounding nature is peaceful and we saw many kinds of birds."
The price is CA $275
CA $499 total
includes taxes & fees
Aug 11 - Aug 12
Big farmhouse in the foothills of the Berkshires
Lake Congamond Cozy Stylish Comfortable House
Enjoy a serene lakeside retreat with a boat dock and tranquil views.

Lake Congamond Cozy Stylish Comfortable House

2.0 star property
10.0 out of 10, Exceptional, (4)
"This cozy cottage was perfect. It was definitely a great lication and close to a lot of stores. The beds were really comfortable too. Thesellerr was super helpfula sn"
Lake Congamond Cozy Stylish Comfortable House
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Situated in a wooded area, this cabin features a welcoming front porch and a serene, secluded environment.

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (129)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Quiet Cabin On Over 12 Acres Of Woods!
Cozy living space with a central island kitchen, spiral staircase, and comfortable seating area.

Quiet Cabin On Over 12 Acres Of Woods!

10.0 out of 10, Exceptional, (11)
"The property was perfect for our weekend in Becket. The house was very comfortable and the grounds quite beautiful. We enjoyed our visit."
Quiet Cabin On Over 12 Acres Of Woods!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Relax in this serene space with a comfortable chair and a staircase leading to an upper level.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (45)
"The home is very nice and cozy. It really felt like a comfy home."
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
Relax in a serene outdoor space with a shaded table and chairs surrounded by lush greenery.

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi

Historic Williams House 2-bedroom downtown Northampton with AC, WiFi
Cabin Retreat in the Berkshire Woods
Cozy living area with a central staircase, comfortable seating, and dining space.

Cabin Retreat in the Berkshire Woods

Cabin Retreat in the Berkshire Woods
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Relax in a spacious living area with a high ceiling and comfortable seating, perfect for socializing and unwinding.

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

10.0 out of 10, Exceptional, (94)
"Exactly what you want in a ski house!"
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
Secluded Family Home in Serene Stockbridge Woods
Enjoy meals with family and friends in this spacious dining area with a long table and comfortable seating for four.

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (21)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods
Charming 3-bedroom farmhouse in Lenox
Relax on the outdoor deck with Adirondack chairs, perfect for a quiet moment or al fresco dining.

Charming 3-bedroom farmhouse in Lenox

10.0 out of 10, Exceptional, (1)
"House is comfortable and spacious, with a well-supplied kitchen. Hosts had thought of everything we might need. A/C was very helpful in the heat! Perfect location for exploring the Berkshires, and a fairly easy walk into town."
Charming 3-bedroom farmhouse in Lenox
Country Living just minutes from Everything!
Enjoy cooking in this well-lit kitchen with a stainless steel refrigerator, oven, and coffee maker.

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
Country Living just minutes from Everything!
Sophisticated Lenox Retreat by Evergreen Home
Enjoy the serene view from the front deck, surrounded by lush trees and a beautifully manicured lawn.

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home
Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Fridge, microwave, oven, stovetop

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB

Berkshires Cabin: Lake Beach Hot Tub - TheWildeBNB
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $585
CA $1,088 total
includes taxes & fees
Aug 18 - Aug 19
Spacious 5-bedroom house in charming Lee with WiFi
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Relax in the backyard patio area with a table, chairs, and cushioned benches under a pergola.

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
The Creation Station is a cozy place so make yourself at home.
Explore the serene surroundings of this peaceful outdoor space, featuring a tranquil pond and lush greenery.

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

10.0 out of 10, Exceptional, (66)
"This was our second time staying here and we had a great time!"
The price is CA $247
CA $374 total
includes taxes & fees
Aug 26 - Aug 27
The Creation Station is a cozy place so make yourself at home.
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Nice place, well maintained, friendly staff, excellent breakfast. Good location but on a main road in a commercial area. Very convenient and comfortable!"
Jesse 2-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham