Photo by Elizabeth Massa Peroulakis

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Compare 205 Vacation Homes in Chester with updated reviews, rates, and availability.

Historic Farmhouse Near Mountains & Colleges!
Westfield Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (3)
"A group of us traveled quite a distance and were so happy to see the great place for us to stay. The house was beautifully restored and tastefully decorated. We felt at home immediately. There were enough room for all of us to spread out and do work or school studies without interrupting others and the back yard was big enough for the kids to blow off steam. The enclosed sunroom was the most popular room in the entire place. This place was top notch! Absolutely perfect!!"
Historic Farmhouse Near Mountains & Colleges!
Amore Estate - beautiful room with many places to explore and relax in.
October MNT FARM!!

Amore Estate - beautiful room with many places to explore and relax in.

9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Secluded Family Home in Serene Stockbridge Woods
Living area

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (18)
"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
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 537
SAR 830 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Breakfast Nook - wake up to the best sunshine ever!

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

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
View from deck looking over our dock on a still day in last days of October.

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (146)
"Beautiful fall colors surrounding the lake. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Tranquil 3-BR Waterfront Retreat

Tranquil 3-BR Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very clean and nicely decorated. Comfortable vibe. Came to relax and enjoy the fall colors. It looks bigger in the pictures, but was plenty big for the 4 of us. Having laundry was a plus, and enjoyed the ping pong table Loved the duvet covers…so soft. Upstairs bathroom could use a mirror in a better place, as blow drying hair and putting on makeup would be difficult, but just didn’t bother. Hope to go again next fall. "
Tranquil 3-BR Waterfront Retreat
The Creation Station is a cozy place so make yourself at home.
Exterior

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

10.0 out of 10, Exceptional, (61)
"We needed a pet friendly location to stay for one night. This place is amazing. Very unconventional and much more than I needed for my family of four but I would recommend it highly. The host was very helpful and friendly. The property would be great for an adult birthday or an extended family get together. "
The price is SAR 676
SAR 1,057 total
includes taxes & fees
26 Nov - 27 Nov
The Creation Station is a cozy place so make yourself at home.
Amherst, Perfect Location, UMass, Smith, MHC!
The Valley is known for our picturesque red tobacco barns and expansive cornfields.

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Lenox Vacation Rental | 3BR | 2BA | 2,457 Sq Ft | Step-Free Access

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (36)
"Fun girl’s weekend in the Berkshires! We will be back! Loved the rental and had lots of space! Beds were comfy and we had a great time. "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Great Room with lake view

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (90)
"Very clean, spacious, and comfortable. Property manager’s information was helpful."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Cozy living room nestled between the oversized kitchen and four-season porch.

4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee

9.6 out of 10, Exceptional, (5)
"This house had everything one could need for a quick getaway or longer stay. It was very comfortable and situated conveniently to Lee, Lenox and Stockbridge. We spent 3 days exploring and found many things to do. I expect to return and we would rent this house again in a heartbeat."
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Sunroom

Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!

10.0 out of 10, Exceptional, (2)
"Delightful property, worked well for our needs"
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Pet-Friendly Westfield Home w/ Fenced Yard!
Westfield Vacation Rental | 4BR | 2BA | Steps to Enter | 1,500 Sq Ft

Pet-Friendly Westfield Home w/ Fenced Yard!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Property worked well for us "
Pet-Friendly Westfield Home w/ Fenced Yard!
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
View of house as seen from road near the brook

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

9.6 out of 10, Exceptional, (125)
"We stayed two days but were mostly for sleep and sightseeing/visits. Certainly fit the bill for our needs. Would recommend to friends "
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Hadley Amherst Location.Explore the Valley Colleges!
Bike ride on the Norwottuck Rail Trail( entrance to trail 2-minutes from the house) to the CT River- Bring your bikes and enjoy!

Hadley Amherst Location.Explore the Valley Colleges!

10.0 out of 10, Exceptional, (129)
"The house was amazing, clean and comfortable. The area was great and very close to restaurants and shopping. I just can’t say enough good things about our experience. If I could give it more than five stars I would. "
Hadley Amherst Location.Explore the Valley Colleges!
Wellspring by AvantStay | Indoor Pool + Views
Welcome!

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views
Find your Sanctuary at The Rectory at Stockbridge
Exterior

Find your Sanctuary at The Rectory at Stockbridge

10.0 out of 10, Exceptional, (6)
"Just a quick stay but a great catch-up. Conveniently located and perfectly clean"
The price is SAR 2,440
SAR 4,026 total
includes taxes & fees
24 Nov - 25 Nov
Find your Sanctuary at The Rectory at Stockbridge
Linny's Updated Lakeview Cottage - Cozy & Modern
Exterior

Linny's Updated Lakeview Cottage - Cozy & Modern

9.8 out of 10, Exceptional, (54)
"Very nice and clean. Great location for proximity to our family"
Linny's Updated Lakeview Cottage - Cozy & Modern
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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Other property types in Chester

Cozy Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

Cozy Berkshires Vacation Rental Near Hiking!

10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 537
SAR 830 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
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.