Photo by Elizabeth Massa Peroulakis

Search Vacation Homes in Chester

    price find illustration
    Change your mind
    Our total price for your stay includes taxes and fees
    deals illustration
    Treat yourself
    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Vacation Homes in Chester

Townhouse with Pool Table - Renovated w/ King Bed
Fridge, microwave, oven, stovetop

Townhouse with Pool Table - Renovated w/ King Bed

10.0 out of 10, Exceptional, (5)
"The home was perfect for our crew while working out of town. Everything was as listed and Mabel was a great host and even called to make sure we were settled in and didn't need anything. "
$315 nightly
The price is $357
Jul 7 - Jul 8
Total includes taxes and fees
Townhouse with Pool Table - Renovated w/ King Bed
Cozy Home in Holyoke with 3 bedrooms
Exterior detail

Cozy Home in Holyoke with 3 bedrooms

9.8 out of 10, Exceptional, (7)
"Wonderful stay. Veronica was so kind and super responsive. The house was a great size and have everything we needed. We stayed there with 2 adults and 2 toddlers under 3. It was plenty of space. And a great location to all the area had to offer, museums, fun restaurants in North Hampton, etc. Would definitely stay again. "
$348 nightly
The price is $389
Jul 1 - Jul 2
Total includes taxes and fees
Cozy Home in Holyoke with 3 bedrooms
Low-scent, historic, well-located, downtown house
Fridge, microwave, oven, stovetop

Low-scent, historic, well-located, downtown house

10.0 out of 10, Exceptional, (4)
"It’s a beautiful home that worked for our stay as a family "
$660 nightly
The price is $737
Jul 26 - Jul 27
Total includes taxes and fees
Low-scent, historic, well-located, downtown house
Button's Modern Luxury Walkup Downtown Northampton
Private kitchen

Button's Modern Luxury Walkup Downtown Northampton

$399 nightly
The price is $446
Jul 1 - Jul 2
Total includes taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
The Creation Station is a cozy place so make yourself at home.
Outdoor dining

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!"
$251 nightly
The price is $280
Jul 1 - Jul 2
Total includes taxes and fees
The Creation Station is a cozy place so make yourself at home.
Big farmhouse in the foothills of the Berkshires
Property grounds

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (136)
"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."
$342 nightly
The price is $362
Jun 30 - Jul 1
Total includes taxes and fees
Big farmhouse in the foothills of the Berkshires
Home in the Woods
Private kitchen

Home in the Woods

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
$303 nightly
The price is $320
Jun 30 - Jul 1
Total includes taxes and fees
Home in the Woods
Charming 3-bedroom Modern cottage with lakeside views
Property grounds

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
$1,314 nightly
The price is $1,487
Jul 2 - Jul 3
Total includes taxes and fees
Charming 3-bedroom Modern cottage with lakeside views
Tranquil Retreat 6-BR Total in the Berkshires
TV, books, offices

Tranquil Retreat 6-BR Total in the Berkshires

$1,303 nightly
The price is $1,455
Jul 7 - Jul 8
Total includes taxes and fees
Tranquil Retreat 6-BR Total in the Berkshires
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

10.0 out of 10, Exceptional, (5)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
$360 nightly
The price is $402
Jul 14 - Jul 15
Total includes taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

$324 nightly
The price is $362
Jul 8 - Jul 9
Total includes taxes and fees
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Property grounds

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
$415 nightly
The price is $464
Jul 16 - Jul 17
Total includes taxes and fees
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
$139 nightly
The price is $155
Jul 6 - Jul 7
Total includes taxes and fees
Deluxe Queen Room with 2 Queen Beds
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

$771 nightly
The price is $861
Jul 16 - Jul 17
Total includes taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free