Photo by Elizabeth Massa Peroulakis

Search Vacation Homes in Chester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 212 Vacation Homes in Chester with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 563
SAR 851 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (202)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake

Charlemont Retreat on Chickley River w/ EV Charger

9.6 out of 10, Exceptional, (21)
"Our family had a wonderful stay. The house was very comfortable and the owner was very responsive. The sound of the river right outside was delightful! The bathrooms are very nicely updated - a nice perk when staying in an older home. "
Charlemont Retreat on Chickley River w/ EV Charger

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!

9.4 out of 10, Exceptional, (39)
"We had a great stay. The house was well furnished, with plenty of space for us, our children, and my parents. There was a nice dining room and a decent kitchen. Our kids loved the arcade machine and air hockey table, and it was a convenient location. The host was very responsive and friendly. The checkout rules were a bit stringent, and it had the quirks of an older house, but overall we loved the place and would highly recommend it to others. "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (84)
"Very nice place, clean, great communication. "
Plainfield House in a 10,000 acre state forest and private pond

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!

Quintessential 6-BR Berkshires Lodge

9.8 out of 10, Exceptional, (9)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (129)
"This was the perfect place to stay while we visited family in Massachusetts. The place was kept beautifully and had all of the amenities to make our visit comfortable. We will definitely book this place in the future."
The price is SAR 807
SAR 1,432 total
includes taxes & fees
12 Jan - 13 Jan
Big farmhouse in the foothills of the Berkshires

Peaceful, Post and Beam Loft, Sleeps 9

10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9

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

10.0 out of 10, Exceptional, (149)
"Highly recommend this house. Wonderful location, plenty of beds for a group. Great communication with the host."
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

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

9.2 out of 10, Wonderful, (20)
"We had a lovely time on our family holiday trip. Andrea was great- easy to get ahold of, clear communication. The house and neighborhood are so charming. Everything was well stocked, comfortable, and even decorated for the holdiays! We’d love to stay again!"
Amore Estate - beautiful room with many places to explore and relax in.

Wellspring by AvantStay | Indoor Pool + Views

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."
Wellspring by AvantStay | Indoor Pool + Views

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (86)
"Simply fantastic!"
Hearts Desire is a furnished whole house in a small, colorful garden center.

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (93)
"Property was beautiful and walkable to town. House is old but very nice. Large enough to accommodate 9 women! Loved sitting outside enjoying perfect weather! All in all had a wonderful experience!"
A Grand property in Historic Stockbridge

Massachusetts Vacation Rental w/ Deck

9.6 out of 10, Exceptional, (17)
"As advertised, easy check-in, good location"
Massachusetts Vacation Rental w/ Deck

Dancing Horse Lodge

9.4 out of 10, Exceptional, (38)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Stockbridge Home: Walk to Town Beach!

9.8 out of 10, Exceptional, (10)
"A friend and I stayed at this property when the Trauma Healing Immersion event at Kripalu had them fully booked. As someone who normally stays at Kripalu when attended events I was hesitant to find property close enough to create an experience that was still as full of peace and solace as I am used to. This property was just what the dr. ordered. I love the bathroom remodel! It was quiet and peaceful which was just what we needed after a long day of lecture and experiential training. "
Stockbridge Home: Walk to Town Beach!

Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (21)
"Very enjoyable time. Nice location. Kari & Glenn made everything easy ."
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chester

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!!

9.8 out of 10, Exceptional, (234)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 563
SAR 851 total
includes taxes & fees
12 Jan - 13 Jan
Berkshire Village Carriage House - Super Private!!

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.