Photo by Elizabeth Massa Peroulakis
Chester Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chester vacation homes
1. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
William C B.
The price is CA $80
CA $408 total
includes taxes & fees
Sep 13 - Sep 14
2. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is CA $202
CA $521 total
includes taxes & fees
Sep 7 - Sep 8
3. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
Frank M.
The price is CA $222
CA $546 total
includes taxes & fees
Sep 7 - Sep 8
4. Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the BerkshiresRussell
10.0 out of 10, Exceptional, (150 reviews)
"Great location"
Will G.
The price is CA $237
CA $459 total
includes taxes & fees
Sep 13 - Sep 14
5. The Creation Station is a cozy place so make yourself at home.
The Creation Station is a cozy place so make yourself at home.Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
Paula
The price is CA $249
CA $389 total
includes taxes & fees
Sep 14 - Sep 15
6. Charming, updated 3 bedroom farmhouse farm stay.
Charming, updated 3 bedroom farmhouse farm stay.Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
Anonymous traveller
The price is CA $351
CA $592 total
includes taxes & fees
Sep 7 - Sep 8
7. Treetop Hideaway in Tyringham
Treetop Hideaway in TyringhamMonterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
Samantha G.
The price is CA $390
CA $803 total
includes taxes & fees
Sep 21 - Sep 22
8. Linny's - Private Dock - Lake Access - Firepit
Linny's - Private Dock - Lake Access - FirepitWest Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
Wendy C.
The price is CA $257
CA $517 total
includes taxes & fees
Sep 13 - Sep 14
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.
Find vacation rentals that suit your style
Apartments
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
8/10 Good
Find out more about Chester
Chester Vacation Homes information
Number of reviews | 417 |
|---|---|
Accommodation | 260 Vacation Homes |
Lowest Price | CA $389 |
Highest Price | CA $2,539 |
Explore a world of travel with Expedia
- B&B in Hadley
- B&B in Florida
- Resorts in Mount Washington
- Motels in Shelburne
- Hotels near Lee Premium Outlets
- Haydenville Hotels
- Resorts in The Berkshires
- Pet-Friendly Hotels in Western Massachusetts
- Relais & Chateaux Hotels in The Berkshires
- Hotels with Kitchenettes in Western Massachusetts
- Pet-Friendly Hotels in The Berkshires
- Cheap Hotels in The Berkshires
- Florence Hotels
- Cabin Rentals in Chicopee
- Becket Hotels
- Cottages in Mill River
- Stockbridge Hotels
- Cheap Hotels in Lee
- Washington Hotels
- The Red Door B&B
- Hotels near Tanglewood Music Center
- Cabin Rentals in Granby
- B&B in Adams
- Hotels with a Lazy River in Western Massachusetts
- Chalets in Western Massachusetts
- Luxury Hotels in The Berkshires
- Resorts in Lenox
- Cottages in The Berkshires
- Easthampton Hotels
- Condo Rentals in Florida
- Quality Inn Westfield
- Historic 1804 house in N Becket Village in the Berkshires
- Hotels near National Shrine of the Divine Mercy
- Hotels with Hot Tubs in Western Massachusetts
- Hotels near Maple Corner Farm Cross Country Ski Area
- Northampton Hotels
- B&B in Russell
- The Whitlock
- Westfield Hotels
- Cabin Rentals in Savoy
- Apartments in Cheshire
- Williamsburg Hotels
- Cabin Rentals in South Amherst
- B&B in Lee
- Country Houses in Alford
- Hotels with an Indoor Pool in Western Massachusetts
- Hotels with a Pool in Western Massachusetts
- Chalets in Becket
- Apartments in Huntington
- Condo Rentals in Granby
- Condo Rentals in Otis
- Motels in Egremont
- B&B in Haydenville
- Cheap Hotels in Sandisfield
- Villas in Beartown State Forest
- Cabin Rentals in Amherst
- Springfield Hotels
- Cabin Rentals in Westfield
- Private Island
- Motels in Granville
- Oceanfront Hotels in Western Massachusetts
- Hupi House
- Southampton Hotels
- Family Hotels in The Berkshires
- Lee Hotels
- Hostels in Springfield
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Chestnut Lodge
- Lenox Hotels
- Flights to Northampton
- Flights from Toronto (YYZ) to Westfield (BAF)
- Flights from Sanya (SYX) to Westfield (BAF)
- Flights to Easthampton
- Flights to Williamsburg
- Flights to The Berkshires
- Flights from Buffalo (BUF) to Westfield (BAF)
- Flights from Wilmington (ILM) to Westfield (BAF)
- Flights from Charleston (CHS) to Westfield (BAF)
- Flights from Becket
- Flights from London (LHR) to Westfield (BAF)
- Flights to Springfield
- Flights to Westfield
- Flights from Montreal (YUL) to Westfield (BAF)
- Flights to Lenox
- Flights to Western Massachusetts
- Flights from Las Vegas (LAS) to Westfield (BAF)