Chester Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Chester holiday rentals

Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (15 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 HK$1,301
HK$2,933 total
includes taxes & fees
6 Apr - 7 Apr
Cozy Home in Holyoke with 3 bedrooms
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (18 reviews)
"We stayed here as a quick overnight trip for events in the area. We really enjoyed the property, reading through the guestbook, and the local pizza place La Figata. "
United States
Kaleigh L.
The price is HK$691
HK$1,403 total
includes taxes & fees
5 Apr - 6 Apr
Peaceful Meadow Retreat
Smart TV, books

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, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,255
HK$3,082 total
includes taxes & fees
9 Apr - 10 Apr
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
1 bedroom, desk, iron/ironing board, travel cot

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, (75 reviews)
"An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again."
United States
Kelly Z.
The price is HK$1,410
HK$2,136 total
includes taxes & fees
9 Apr - 10 Apr
The Creation Station is a cozy place so make yourself at home.
Property grounds

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, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$1,475
HK$3,547 total
includes taxes & fees
2 Apr - 3 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,142
HK$2,895 total
includes taxes & fees
8 Apr - 9 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
3 bedrooms, desk, iron/ironing board, travel cot

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (12 reviews)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
The price is HK$1,410
HK$3,022 total
includes taxes & fees
9 Apr - 10 Apr
Townhouse with Pool Table - Renovated w/ King Bed
Interior

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (2 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$1,970
HK$3,960 total
includes taxes & fees
2 Apr - 3 Apr
Button's Modern Luxury Walkup Downtown Northampton
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (144 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is HK$1,411
HK$2,618 total
includes taxes & fees
15 Apr - 16 Apr
Big farmhouse in the foothills of the Berkshires
TV

Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4 reviews)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
The price is HK$776
HK$2,138 total
includes taxes & fees
9 Apr - 10 Apr
Charming Chicopee Getaway
Living area

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (3 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is HK$1,136
HK$1,645 total
includes taxes & fees
9 Apr - 10 Apr
Cozy 2-bedroom apartment in Chicopee
Property grounds

Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is HK$5,485
HK$6,879 total
includes taxes & fees
14 Apr - 15 Apr
Cozy Valley View Post & Beam Villa!
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,587
HK$2,481 total
includes taxes & fees
2 Apr - 3 Apr
Cozy Riverside Berkshires Retreat
Interior

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is HK$1,904
HK$4,267 total
includes taxes & fees
13 Apr - 14 Apr
12-acre Vacation Rental in the Berkshires!
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,109
HK$3,896 total
includes taxes & fees
5 Apr - 6 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior

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, (35 reviews)
"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"
United States
Susan
The price is HK$2,813
HK$5,689 total
includes taxes & fees
3 Apr - 4 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.8 out of 10, Exceptional, (6 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is HK$1,453
HK$3,653 total
includes taxes & fees
5 Apr - 6 Apr
Sun Filled Lenox Retreat - Minutes to Tanglewood!
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,070
HK$4,358 total
includes taxes & fees
22 Apr - 23 Apr
Treetop Hideaway in Tyringham
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,351
HK$6,283 total
includes taxes & fees
8 Apr - 9 Apr
Spacious 5-bedroom house in charming Lee with WiFi
Dining

Humble home with free breakfast

Humble home with free breakfast
Chicopee
5.4 out of 10, (3 reviews)
"This host cancelled my booking 3 hours after our check in time. We had already arrived and were left stranded with no where to stay."
United States
Kathleen D.
The price is HK$972
HK$2,385 total
includes taxes & fees
12 Apr - 13 Apr
Humble home with free breakfast
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"this has been absolutely amazing and incredible for incredibly difficult time for our family because of family medical emergency. everyone has been so amazing and beautiful and healing for our loved ones and we are grateful to be close to then"
Chris 3-night trip
Posted 7 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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?

Peace and quiet on the lake: This holiday home rental outside of Chester is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like Berkshire Scenic Railway Museum, or get outside and enjoy nature at Pyramid Lake. Chester Town Hall and Jacob's Pillow 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.