Chester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Chester vacation 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, (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 ￥19,830
￥49,412 total
includes taxes & fees
Feb 25 - Feb 26
Cozy Home in Holyoke with 3 bedrooms
Property grounds

Peaceful Meadow Retreat

Peaceful Meadow Retreat
Granby
10.0 out of 10, Exceptional, (17 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 ￥14,449
￥28,580 total
includes taxes & fees
Jan 29 - Jan 30
Peaceful Meadow Retreat
Desk, iron/ironing board, travel crib, 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.
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 ￥27,457
￥41,233 total
includes taxes & fees
Feb 24 - Feb 25
The Creation Station is a cozy place so make yourself at home.
3 bedrooms, desk, iron/ironing board, travel crib

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 ￥27,787
￥59,722 total
includes taxes & fees
Jan 29 - Jan 30
Townhouse with Pool Table - Renovated w/ King Bed
Private kitchen

Welcoming 3-bedroom house- Gardner home

Welcoming 3-bedroom house- Gardner home
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 ￥18,524
￥53,767 total
includes taxes & fees
Jan 29 - Jan 30
Welcoming 3-bedroom house- Gardner home
WiFi, bed sheets

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 ￥20,840
￥32,049 total
includes taxes & fees
Jan 29 - Jan 30
Cozy Rustic Apt in 18th c Berkshire Farmhouse
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, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥30,508
￥55,465 total
includes taxes & fees
Feb 2 - Feb 3
Big farmhouse in the foothills of the Berkshires
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, (35 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥25,008
￥64,835 total
includes taxes & fees
Jan 29 - Jan 30
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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
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 ￥24,437
￥58,136 total
includes taxes & fees
Feb 2 - Feb 3
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Living area

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 ￥21,203
￥31,323 total
includes taxes & fees
Feb 28 - Mar 1
Cozy 2-bedroom apartment in Chicopee
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (8 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ￥30,889
￥45,408 total
includes taxes & fees
Feb 2 - Feb 3
Family Ski Getaway in the Berkshires
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 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 ￥27,787
￥71,041 total
includes taxes & fees
Jan 29 - Jan 30
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 ￥50,788
￥93,113 total
includes taxes & fees
Feb 2 - Feb 3
Button's Modern Luxury Walkup Downtown Northampton
Exterior detail

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ￥32,263
￥52,419 total
includes taxes & fees
Feb 23 - Feb 24
3-bedroom house in beautiful Berkshires, close to amenities!
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 ￥18,524
￥46,970 total
includes taxes & fees
Feb 16 - Feb 17
Humble home with free breakfast
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, (33 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 ￥45,609
￥99,164 total
includes taxes & fees
Feb 2 - Feb 3
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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 ￥41,049
￥75,329 total
includes taxes & fees
Feb 2 - Feb 3
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 ￥92,622
￥116,736 total
includes taxes & fees
Feb 2 - Feb 3
Cozy Valley View Post & Beam Villa!
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 ￥73,326
￥132,945 total
includes taxes & fees
Feb 12 - Feb 13
Spacious 5-bedroom house in charming Lee with WiFi
Dining

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Patrick was super nice and his farmers market/ cafe is great. Got to cut my own flowers from his field for free! I would definitely stay there again if in the area."
United States
Patricia A.
The price is ￥20,840
￥32,049 total
includes taxes & fees
Jan 29 - Jan 30
Charming Apt in 18th c Berkshire Farmhouse
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 Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Everything good"
Herika 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

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:

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

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Chester vacation home rental. It offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Pyramid Lake. Chester Town Hall and Hiram H. Fox Wildlife Management Area 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.