Photo by Elizabeth Massa Peroulakis
Chester Vacation Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Chester Vacation Homes

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (217)

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (127)

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.6 out of 10, Exceptional, (14)

Deluxe Queen Room with 2 Queen Beds
Deluxe Queen Room with 2 Queen Beds
2.0 out of 10, (3)
The price is CA $136
CA $183 total
includes taxes & fees
Sep 1 - Sep 2

Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (139)
The price is CA $275
CA $499 total
includes taxes & fees
Aug 11 - Aug 12

Lake Congamond Cozy Stylish Comfortable House
Lake Congamond Cozy Stylish Comfortable House
10.0 out of 10, Exceptional, (4)

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (129)

Quiet Cabin On Over 12 Acres Of Woods!
Quiet Cabin On Over 12 Acres Of Woods!
10.0 out of 10, Exceptional, (11)
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
Top Chester Hotel Reviews

The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Find out more about Chester
Find out more about Chester
Chester Vacation Homes information
Number of reviews | 975 |
---|---|
Accommodation | 297 Vacation Homes |
Lowest Price | CA $136 |
Highest Price | CA $585 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Vacation Homes in Other Destinations
More Accommodation Types in Chester
- Cottages in Chester
- Apartments in Chester
- Cabin Rentals in Chester
- Motels in Chester
- B&B in Chester
- Farmstay in Chester
- Condo Rentals in Chester
- Guest Houses in Chester
- Resorts in Chester
- Inns in Chester
- Chalets in Chester
- Lodges in Chester
- Villas in Chester
- Castles in Chester
- Condo Resorts in Chester
- Hotels
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
More ways to book
Expedia's Latest Trends
Hotels