Photo by Elizabeth Massa Peroulakis

Chester Holiday Rentals

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Our top choices for Chester holiday rentals

Apartment in Granby

Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (17 reviews)
"The place is beautiful and very quiet and relaxing"
United States
Marian
The price is AU$280
includes taxes & fees
13 Jan - 14 Jan
Peaceful Meadow Retreat
10.0 out of 10, Exceptional, (72 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 AU$343
includes taxes & fees
12 Jan - 13 Jan
The Creation Station is a cozy place so make yourself at home.
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 AU$481
includes taxes & fees
13 Jan - 14 Jan
Cozy Home in Holyoke with 3 bedrooms
2.0 star property
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 AU$504
includes taxes & fees
13 Jan - 14 Jan
Welcoming 3-bedroom house- Gardner home
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 AU$558
includes taxes & fees
12 Jan - 13 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
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 AU$566
includes taxes & fees
12 Jan - 13 Jan
Townhouse with Pool Table - Renovated w/ King Bed
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 AU$586
includes taxes & fees
12 Jan - 13 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
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 AU$747
includes taxes & fees
16 Jan - 17 Jan
Little Longbow Lakefront Chalet
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
The price is AU$312
includes taxes & fees
24 Jan - 25 Jan
Cozy Rustic Apt in 18th c Berkshire Farmhouse
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 AU$621
includes taxes & fees
12 Jan - 13 Jan
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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 AU$307
includes taxes & fees
14 Jan - 15 Jan
Cozy 2-bedroom apartment in Chicopee
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AU$536
includes taxes & fees
12 Jan - 13 Jan
Big farmhouse in the foothills of the Berkshires
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 AU$667
includes taxes & fees
12 Jan - 13 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 AU$846
includes taxes & fees
15 Jan - 16 Jan
Owl`s Nest - Cozy Westfield Home w/ Fire Pit
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 AU$721
includes taxes & fees
12 Jan - 13 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 AU$888
includes taxes & fees
12 Jan - 13 Jan
Button's Modern Luxury Walkup Downtown Northampton

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
United States
Kathy C.
The price is AU$441
includes taxes & fees
12 Jan - 13 Jan
Family Ski Getaway in the Berkshires
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 AU$939
includes taxes & fees
19 Jan - 20 Jan
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AU$1,113
includes taxes & fees
12 Jan - 13 Jan
Cozy Valley View Post & Beam Villa!
2.0 star property
The price is AU$549
includes taxes & fees
12 Jan - 13 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

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$441 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.