A river flowing through a forest with autumn-colored trees.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chester vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,271 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is AED 282
AED 397 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A spacious living room with a wooden staircase, a dining area, and a television.

2. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AED 220
AED 1,038 total
includes taxes & fees
18 Nov - 19 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A triangular-shaped building with a balcony and a wooden picnic table in front.

3. 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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is AED 536
AED 1,320 total
includes taxes & fees
15 Nov - 16 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

4. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AED 588
AED 1,383 total
includes taxes & fees
15 Nov - 16 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A white porch with two rocking chairs, a door, and a number '205'.

5. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (156 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AED 727
AED 1,270 total
includes taxes & fees
15 Nov - 16 Nov
Big farmhouse in the foothills of the Berkshires
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

6. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is AED 681
AED 1,581 total
includes taxes & fees
16 Nov - 17 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

7. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is AED 906
AED 1,458 total
includes taxes & fees
6 Dec - 7 Dec
Charming, updated 3 bedroom farmhouse farm stay.
A rural property with a wooden barn, a white fence, and a mobile home.

8. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
10.0 out of 10, Exceptional, (1 review)
"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...
United States
hannah w.
The price is AED 529
AED 640 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Camper tucked into the woods
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

9. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is AED 209
AED 829 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

10. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is AED 413
AED 1,097 total
includes taxes & fees
17 Nov - 18 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A hot tub on a wooden deck with snow on the ground and trees in the background.

11. 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, (79 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!"
United States
Paula
The price is AED 661
AED 976 total
includes taxes & fees
18 Nov - 19 Nov
The Creation Station is a cozy place so make yourself at home.
A two-story residential building with a sign indicating 'Victory Residence' and the address '1785'.

12. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is AED 209
AED 1,059 total
includes taxes & fees
22 Nov - 23 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a pool table.

13. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (20 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AED 744
AED 1,540 total
includes taxes & fees
16 Nov - 17 Nov
Townhouse with Pool Table - Renovated w/ King Bed
A rustic wooden building with a chimney, surrounded by lush greenery and flowering plants.

14. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is AED 1,297
AED 2,375 total
includes taxes & fees
14 Dec - 15 Dec
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A picnic table in a grassy yard with trees and a fence in the background.

15. A Cozy Berkshire Escape l Close to the Slopes

A Cozy Berkshire Escape l Close to the Slopes
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AED 744
AED 1,102 total
includes taxes & fees
16 Nov - 17 Nov
A Cozy Berkshire Escape l Close to the Slopes
A modern kitchen with a central island, bar stools, and a bicycle.

16. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is AED 897
AED 1,748 total
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

17. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is AED 316
AED 855 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A covered porch with string lights, a ceiling fan, and outdoor seating.

18. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AED 1,253
AED 2,187 total
includes taxes & fees
16 Nov - 17 Nov
Secluded Family Home in Serene Stockbridge Woods
A two-story house with a front porch, a concrete walkway, and a well-maintained lawn.

19. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is AED 544
AED 1,231 total
includes taxes & fees
27 Nov - 28 Nov
Cozy Home in Holyoke with 3 bedrooms
A living room with a fireplace, a sofa, a coffee table, and a TV.

20. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is AED 628
AED 858 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 2-bedroom apartment in Chicopee
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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Top Chester Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Loved the fireplace in the room."
barbara 1-night trip
Posted 5 hours ago
D. Hotel Suites & Spa

Frequently asked questions

Can I find a vacation rental in Chester?

Yes, you can find vacation rentals close to well known sights in Chester, or you can select a more secluded option if you want a relaxing place to stay. Chester is known for its waterfalls and shopping. Make sure you have time to check out the riverfront and restaurants during your trip.

What are some of the best vacation rentals that Chester has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: Visitors like this Chester vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Glendale Falls. Chester Town Hall and Pyramid Lake are a couple of places you'll find in the larger area.

What are vacation rentals like in Chester?

Vacation rentals are privately owned accommodations you can book for a short or long stay in Chester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.