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Chester Vacation Rentals

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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chester vacation rentals

Outdoor spa tub

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is SAR 602
SAR 1,477 total
includes taxes & fees
10 Sep - 11 Sep
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

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."
United States
Sharon K.
The price is SAR 547
SAR 1,408 total
includes taxes & fees
8 Sep - 9 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,132 reviews)
"Clean & comfortable stay"
United States
Robert
The price is SAR 299
SAR 418 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Property grounds

4. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (150 reviews)
"Great location"
United States
Will G.
The price is SAR 713
SAR 1,322 total
includes taxes & fees
8 Sep - 9 Sep
Big farmhouse in the foothills of the Berkshires
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood 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!"
United States
William C B.
The price is SAR 222
SAR 1,124 total
includes taxes & fees
13 Sep - 14 Sep
Real Estate: Therapy - Lake, Laundry, Love it
2 bedrooms, WiFi, bed sheets

6. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Otis
The price is SAR 825
SAR 1,282 total
includes taxes & fees
8 Sep - 9 Sep
Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature
Property grounds

7. 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. "
United States
Anonymous traveler
The price is SAR 953
SAR 1,595 total
includes taxes & fees
8 Sep - 9 Sep
Charming, updated 3 bedroom farmhouse farm stay.
Desk, iron/ironing board, travel crib, WiFi

8. 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!"
United States
Paula
The price is SAR 676
SAR 1,057 total
includes taxes & fees
14 Sep - 15 Sep
The Creation Station is a cozy place so make yourself at home.
Outdoor dining

9. Cozy Camper tucked into the woods

Cozy Camper tucked into the woods
Sandisfield
The price is SAR 683
SAR 872 total
includes taxes & fees
14 Sep - 15 Sep
Cozy Camper tucked into the woods
TV

10. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
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!! "
United States
Samantha G.
The price is SAR 1,074
SAR 2,187 total
includes taxes & fees
15 Sep - 16 Sep
Treetop Hideaway in Tyringham
Property grounds

11. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (11 reviews)
"This property was amazing. It is private and beautiful. The view is amazing. The decor is comfortable with plenty of seating for all. Perfectly stocked with everything you could want. All the rooms were comfortable and spotless. I would definitely stay here again if the occasion arose. The owner was so responsive and kind. It was as perfect as could be."
United States
Sharon C.
The price is SAR 1,878
SAR 2,374 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Valley View Post & Beam Villa!
Coffee/tea maker, fridge, microwave, oven

12. 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, (31 reviews)
"Excellent area for hiking the Berkshires! House is clean, comfortable, and perfect for cooking a quick dinner after showering off the mud and pine needles. Dog friendly. Right off the main street of a very nice neighborhood."
United States
Elizabeth G.
The price is SAR 490
SAR 1,214 total
includes taxes & fees
10 Sep - 11 Sep
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Apartment (0 Bedroom) | Interior

13. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is SAR 342
SAR 895 total
includes taxes & fees
12 Sep - 13 Sep
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Interior

14. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is SAR 760
SAR 1,189 total
includes taxes & fees
8 Sep - 9 Sep
Riverside Retreat in the Berkshires
Exterior

15. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is SAR 1,727
SAR 3,213 total
includes taxes & fees
28 Sep - 29 Sep
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

16. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 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 SAR 917
SAR 1,875 total
includes taxes & fees
8 Sep - 9 Sep
Button's Modern Luxury Walkup Downtown Northampton
Interior

17. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is SAR 697
SAR 1,407 total
includes taxes & fees
13 Sep - 14 Sep
Linny's - Private Dock - Lake Access - Firepit
3 bedrooms, desk, iron/ironing board, travel crib

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is SAR 899
SAR 1,846 total
includes taxes & fees
15 Sep - 16 Sep
Townhouse with Pool Table - Renovated w/ King Bed
Flat-screen TV, books

19. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (12 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
The price is SAR 635
SAR 1,159 total
includes taxes & fees
13 Sep - 14 Sep
Cozy First Floor Apartment. Located in a quiet neighborhood.
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

Blue A Modern Hotel, an Ascend Collection Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent
"This place is an absolute gem. Very spacious parking for larger vehicles, trailers, buses, etc. The staff is world class and so friendly. The rooms are very modern and so clean. AMAZING COFFEE!!!! Highly recommend"
Chad 2-night trip
Posted less than an hour ago
Blue A Modern Hotel, an Ascend Collection Hotel

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 Becket Land Trust Historic Quarry. Chester Town Hall and Jacob's Pillow 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.