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Check prices for these dates

Next weekend
16 Jum. I - 18 Jum. I
In two weeks
23 Jum. I - 25 Jum. I
In one month
6 Jum. II - 8 Jum. II
In two months
4 Raj. - 6 Raj.

Compare 276 Vacation Homes in Chester with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (245)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is SAR 563
SAR 855 total
includes taxes & fees
13 May - 14 May
Berkshire Village Carriage House - Super Private!!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior

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

10.0 out of 10, Exceptional, (151)
"Hi,The views are spectacular, house is spacious and close to skiing. We had a great time staying in this house. We even talked about coming back in warmer weather. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"We enjoyed the privacy and quiet of the location. The house itself is very well kept inside and cozy. "
Peace and quiet on the lake
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (71)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!
Owl's Nest - Cozy Westfield Home w/ Fire Pit
Fridge, microwave, oven, stovetop

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.0 out of 10, Wonderful, (4)
"Property worked well for us "
The price is SAR 738
SAR 1,914 total
includes taxes & fees
8 Jun - 9 Jun
Owl's Nest - Cozy Westfield Home w/ Fire Pit
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Hilltown Nest is a wonderful place for family and friends to gather.
Property grounds

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.
Mountain Blossom Retreat by Evergreen Home
A heated pool

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Exterior

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"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."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

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

10.0 out of 10, Exceptional, (121)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Amherst, Perfect Location, UMass, Smith, MHC!
Outdoor dining

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"House was great, very comfortable, location was perfect for our needs. All of us had an excellent stay."
Amherst, Perfect Location, UMass, Smith, MHC!
Historic Farmhouse Near Mountains & Colleges!
Fridge, microwave, stovetop, dishwasher

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (7)
"Loved our stay at this adorable ranch home. Cute and comfy and clean. "
Historic Farmhouse Near Mountains & Colleges!
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
Lakeside 5-BR Home in Idyllic Berkshires
TV, fireplace, offices

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (2)
"Celebrated a birthday with a group of old friends. Great location near Lee. Enjoyed the lake views. Fires inside and outside. Home is well decorated and clean."
Lakeside 5-BR Home in Idyllic Berkshires
Rustic 3bd Lake Front Country Cottage
Smart TV, fireplace, stereo

Rustic 3bd Lake Front Country Cottage

9.4 out of 10, Exceptional, (3)
"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."
Rustic 3bd Lake Front Country Cottage
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (94)
"Great location and beautifully appointed house. Cindy is very helpful and responsive."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
Stockbridge Village Cottage With Mountain View’s and walk to town
Fridge, microwave, oven, stovetop

Stockbridge Village Cottage With Mountain View’s and walk to town

10.0 out of 10, Exceptional, (58)
"Great house, fully stocked kitchen, lots of cozy places to snuggle up, great location"
Stockbridge Village Cottage With Mountain View’s and walk to town
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

The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is SAR 446
SAR 582 total
includes taxes & fees
11 May - 12 May
Deluxe Queen Room with 2 Queen Beds
Cozy Home in Holyoke with 2 bedrooms
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 2 bedrooms

10.0 out of 10, Exceptional, (4)
"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!! "
The price is SAR 488
SAR 1,085 total
includes taxes & fees
12 May - 13 May
Cozy Home in Holyoke with 2 bedrooms
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.