Photo by Elizabeth Massa Peroulakis

Chester Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chester holiday rentals

Property grounds
Peaceful Meadow Retreat

Peaceful Meadow Retreat

Peaceful Meadow Retreat
2.0 star property
Granby
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful property comfy, cozy and clean little cottage."
United States
Denise T.
The price is HK$730
HK$1,443 total
includes taxes & fees
14 Jan - 15 Jan
Peaceful Meadow Retreat
Desk, iron/ironing board, travel cot, WiFi
The Creation Station is a cozy place so make yourself at home.

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, (73 reviews)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is HK$1,091
HK$1,741 total
includes taxes & fees
13 Jan - 14 Jan
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop
Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (13 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is HK$1,013
HK$2,508 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Home in Holyoke with 3 bedrooms
Private kitchen
Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
2.0 star property
Chicopee
10.0 out of 10, Exceptional, (1 review)
"Overall had a great stay, the space is cozy and welcoming."
United States
Gracie B.
The price is HK$935
HK$2,635 total
includes taxes & fees
13 Jan - 14 Jan
Welcoming 3-bedroom house- Gardner home
Interior
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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$1,136
HK$2,932 total
includes taxes & fees
13 Jan - 14 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
3 bedrooms, desk, iron/ironing board, travel cot
Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (11 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$1,403
HK$2,998 total
includes taxes & fees
13 Jan - 14 Jan
Townhouse with Pool Table - Renovated w/ King Bed
Smart TV, books
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is HK$1,249
HK$3,075 total
includes taxes & fees
13 Jan - 14 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Outdoor dining
Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet
Becket
9.8 out of 10, Exceptional, (21 reviews)
"Absolutely perfect quiet get away to relax and recharge will be back! "
United States
Dana V.
The price is HK$2,280
HK$3,975 total
includes taxes & fees
16 Jan - 17 Jan
Little Longbow Lakefront Chalet
WiFi, bed sheets
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse
Lanesborough
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
The price is HK$1,052
HK$1,601 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Property grounds
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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, (35 reviews)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is HK$1,298
HK$3,313 total
includes taxes & fees
13 Jan - 14 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Living area
Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (2 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is HK$1,083
HK$1,583 total
includes taxes & fees
14 Jan - 15 Jan
Cozy 2-bedroom apartment in Chicopee
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is HK$1,403
HK$2,653 total
includes taxes & fees
25 Jan - 26 Jan
Big farmhouse in the foothills of the Berkshires
Smart TV, books
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is HK$1,403
HK$3,587 total
includes taxes & fees
13 Jan - 14 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Smart TV, fireplace, ping pong, offices
Owl`s Nest - Cozy Westfield Home w/ Fire Pit

Owl`s Nest - Cozy Westfield Home w/ Fire Pit

Owl`s Nest - Cozy Westfield Home w/ Fire Pit
Westfield
9.6 out of 10, Exceptional, (9 reviews)
"Great place for a large family get together, convenient to downtown Westfield. Nice big fenced yard, good for dogs. "
United States
Harry M.
The price is HK$1,608
HK$4,478 total
includes taxes & fees
15 Jan - 16 Jan
Owl`s Nest - Cozy Westfield Home w/ Fire Pit
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!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
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$2,098
HK$3,797 total
includes taxes & fees
13 Jan - 14 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior
Button's Modern Luxury Walkup Downtown Northampton

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$2,564
HK$4,702 total
includes taxes & fees
13 Jan - 14 Jan
Button's Modern Luxury Walkup Downtown Northampton
Interior
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,578
HK$2,320 total
includes taxes & fees
13 Jan - 14 Jan
Family Ski Getaway in the Berkshires
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!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (32 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,331
HK$5,006 total
includes taxes & fees
19 Jan - 20 Jan
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds
Cozy Valley View Post & Beam Villa!

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$4,677
HK$5,894 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Valley View Post & Beam Villa!
Private kitchen
Updated and inviting home in Lenoxdale

Updated and inviting home in Lenoxdale

Updated and inviting home in Lenoxdale
2.0 star property
Lee
The price is HK$1,179
HK$2,927 total
includes taxes & fees
13 Jan - 14 Jan
Updated and inviting home in Lenoxdale
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

Hampton Inn Chicopee/Springfield

Hampton Inn Chicopee/Springfield

10/10 Excellent
"Clean room, courteous staff and all the amenities you could want. "
Jeanann 2-night trip
Posted 2 days ago
Hampton Inn Chicopee/Springfield

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside of Chester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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 selection of games and 1 hot tub.

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 Skyline Trail 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.