Photo by Elizabeth Massa Peroulakis

Chester Holiday Rentals

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Holiday Rentals in Chester

Cozy Berkshires Vacation Rental Near Hiking!
Cozy Berkshires Vacation Rental Near Hiking!
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, 35 reviews
"Very clean and nice apartment in a pleasant little city."
The price is AU$394
per night
1 July - 2 July
Cozy apartment located in quiet Williamsburg
Peace and quiet on the lake
9.6 out of 10, Exceptional, 187 reviews
"Cute & clean house, awesome location right on the water, great for swimming/fishing/kayaking plus super close to the store for any supplies. Thanks again!"
Peace and quiet on the lake
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, 195 reviews
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, 53 reviews
"Wonderful place to stay, had a great time lots of instruments to try, had lots of space to spread out and hangout, the hot tub was very nice and clean. Overall had a fantastic stay the lighted walkway is amazing! All the amenities available where also great, Jon was a great host and we had a great time speaking with him!"
The price is AU$426
per night
1 July - 2 July
The Creation Station is a cozy place so make yourself at home.
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, 8 reviews
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, 32 reviews
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, 118 reviews
"Comfortable, quiet and convenient country location. This is our third time staying at the property for fishing and exploring the Deerfield and Westfield rivers and we will definitely return."
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, 5 reviews
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
9.4 out of 10, Exceptional, 52 reviews
"We were in town for our daughter’s graduation and loved Michelle’s cottage. The house was just right for our family, sharing dinners and celebrating our graduate. The bedding in the house was great, comfy and soft. Lots of cute spaces and well equipped house! Michelle was a great communicator and was available if we had any questions. We loved our stay."
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, 206 reviews
"We loved our long weekend here—so comfortable and clean and private. Just perfect for two!"
Berkshire Village Carriage House - Super Private!!
Berkshire Lake access
10.0 out of 10, Exceptional, 41 reviews
"Living space is bigger than the pictures, plenty of room for everyone, well stocked kitchen, everything we needed!"
Berkshire Lake access
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, 2 reviews
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, 49 reviews
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is AU$412
per night
8 July - 9 July
Perfect Vacation Get Away - Historical New Marlborough
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, 4 reviews
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
9.6 out of 10, Exceptional, 7 reviews
"We were racing at Southwick motocross park. This location appealed to us because it had a lake to swim in, nice quiet neighborhood and house looked cozy. Everything was amazing. The local stores, restaurants and things to do was great. This is a very quiet neighborhood and so relaxing. The house was great, all amenities were as described. We really enjoyed it."
Pet-Friendly Tolland Cabin w/ Private Hot Tub!
Hadley Amherst Location.Explore the Valley Colleges!
10.0 out of 10, Exceptional, 124 reviews
"Stayed here for my child’s graduation weekend. Enough room for everyone and great location. Loved the nearby walking trail!"
Hadley Amherst Location.Explore the Valley Colleges!
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, 18 reviews
"Our stay at this cottage was wonderful. The property was perfect size for us and we enjoyed golfing at Bas Ridge Golf Course, even though the weather was not the greatest that day. The hot tub was such a great amenity and we enjoyed the nice quiet location!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 21 reviews
"The rental property was just as described online. We had a very relaxing time. We also enjoyed playing all the games provided. This is a beautiful location and very quiet area. We loved sitting out in the hot tub at night looking up at the stars. Really special experience."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Amherst, Perfect Location, UMass, Smith, MHC!
10.0 out of 10, Exceptional, 12 reviews
"It was a nice house in a quiet neighborhood, the amenities were up to date and very comfortable place to spend our time."
Amherst, Perfect Location, UMass, Smith, MHC!
Don't see what you're looking for?
See all available properties in Chester
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.

Chester Holiday Home Travel Info

Other types of properties in Chester you may be interested in

Quality Inn West Springfield
2.5 star property
7.2 out of 10, Good, 1,002 reviews
"Great"
The price is AU$151
per night
3 July - 4 July
Quality Inn West Springfield
D. Hotel Suites & Spa
3.0 star property
9.4 out of 10, Exceptional, 2,281 reviews
"Very nice hotel... and James at the desk was amazing!!!"
The price is AU$254
per night
1 July - 2 July
D. Hotel Suites & Spa
La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
8.2 out of 10, Very good, 1,255 reviews
"Staff was attentive to our needs. Welcoming to young people. Friendly. Respectful. Breakfast was good , but should upgrade the quality of the plastic utensils."
The price is AU$200
per night
1 July - 2 July
La Quinta Inn & Suites by Wyndham Springfield MA
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.

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$394 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 apartment located in quiet Williamsburg: This holiday home rental outside of Chester is in a rural location, and equipped with air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Otis Reservoir. 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.

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