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Chester Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chester holiday rentals

Lobby

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,077 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
The price is HK$742
HK$1,004 total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge
Outdoor spa tub

2. 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 HK$1,313
HK$3,184 total
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

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, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,334
HK$3,208 total
includes taxes & fees
25 Aug - 26 Aug
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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, (149 reviews)
"Great location"
United States
Will G.
The price is HK$1,490
HK$2,786 total
includes taxes & fees
16 Sept - 17 Sept
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
The price is HK$486
HK$2,366 total
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
Property grounds

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, (39 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is HK$2,040
HK$4,110 total
includes taxes & fees
20 Aug - 21 Aug
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 traveller
The price is HK$1,906
HK$3,250 total
includes taxes & fees
31 Aug - 1 Sept
Charming, updated 3 bedroom farmhouse farm stay.
Interior

8. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
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 HK$1,527
HK$2,389 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Riverside Berkshires Retreat
TV

9. 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 HK$2,228
HK$4,552 total
includes taxes & fees
16 Sept - 17 Sept
Treetop Hideaway in Tyringham
4 bedrooms, travel cot, WiFi, bed sheets

10. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is HK$3,989
HK$6,848 total
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape
Coffee/tea maker, fridge, microwave, oven

11. 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)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is HK$1,024
HK$2,563 total
includes taxes & fees
31 Aug - 1 Sept
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Desk, iron/ironing board, travel cot, WiFi

12. 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 HK$1,412
HK$2,103 total
includes taxes & fees
15 Sept - 16 Sept
The Creation Station is a cozy place so make yourself at home.
3 bedrooms, desk, iron/ironing board, travel cot

13. 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 HK$2,005
HK$4,028 total
includes taxes & fees
25 Aug - 26 Aug
Townhouse with Pool Table - Renovated w/ King Bed
Property grounds

14. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (10 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is HK$3,922
HK$5,003 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Valley View Post & Beam Villa!
Interior

15. 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 HK$1,915
HK$3,944 total
includes taxes & fees
25 Aug - 26 Aug
Button's Modern Luxury Walkup Downtown Northampton
Exterior

16. Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is HK$557
HK$2,015 total
includes taxes & fees
20 Aug - 21 Aug
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Outdoor dining

17. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is HK$3,157
HK$4,985 total
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Smart TV

18. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,313
HK$3,079 total
includes taxes & fees
17 Sept - 18 Sept
stylish Berkshires Retreat
Interior

19. 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 HK$784
HK$1,948 total
includes taxes & fees
31 Aug - 1 Sept
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Interior

20. 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 HK$1,592
HK$3,150 total
includes taxes & fees
13 Sept - 14 Sept
Linny's - Private Dock - Lake Access - Firepit
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

The Ellery

The Ellery

10/10 Excellent
"Very quiet and convenient location"
Elizabeth 3-night trip
Posted 2 hours ago
The Ellery

Find out more about Chester

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Frequently asked questions

Can I find a holiday rental in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chester has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Chester is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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 Littleville Lake. Chester Town Hall and Glendale Falls are a couple of places you'll find in the wider area.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family gatherings.