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Chester Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Chester

Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The price is HK$1,079
HK$1,206 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Games room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,574
HK$2,313 total
includes taxes & fees
14 Nov - 15 Nov
Pet Friendly Riverfront Home in Great Barrington
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Interior
Peace and quiet on the lake

Peace and quiet on the lake

Sherwood Forest
9.6 out of 10, Exceptional, (228)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Dining
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee
9.6 out of 10, Exceptional, (17)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
United States
Annie C.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Outdoor pool
The Clearing - Quiet - Close To Nature

The Clearing - Quiet - Close To Nature

Cummington
10.0 out of 10, Exceptional, (207)
"It was a warm place. John was kind. "
United States
Seung Gyou B.
The Clearing - Quiet - Close To Nature
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$3,303
HK$6,146 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
Outdoor dining
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (149)
"You'll do some walking and stair climbing but otherwise was just what we needed and wanted! Owner was very accommodating when we had to bring the grandpup unexpectedly. Definitely recommend staying here."
United States
Wendy Cameron L.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lee
9.4 out of 10, Exceptional, (71)
"Liked the 3 room suite, and 100 year old oak interior and the front porch, esp. as time went on. Walk to many restaurants, some only open in Fall after Wednesday. Some of the old doors fit like old doors, not unexpected, and felt like home away from home as time went on. Liked Fridge, coffee maker and small kitchen that we hardly used, but would have used more if longer stay."
United States
Leonard
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Property grounds
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, (70)
"A very short but a really fun stay. Great location to just relax and get away from it all."
United States
Naseem P.
The price is HK$1,399
HK$2,161 total
includes taxes & fees
18 Nov - 19 Nov
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop
Charming Chicopee Getaway

Charming Chicopee Getaway

Chicopee
6.0 out of 10, (2)
"The apartment didn't look anything like the pictures. It was dingy and had a smell to it that we couldn't tolerate and that lingered in our nostrils for hours after we left. The kitchen area was unusable -- what passed for a table was at the same level as the chair seats, which made it impossible to use. Finally, we had to move a big trash bag full of trash out of the way before even being able to get in the door. We left within minutes after arriving and went to a hotel. "
United States
Kenneth M.
The price is HK$692
HK$2,021 total
includes taxes & fees
17 Nov - 18 Nov
Charming Chicopee Getaway
Property grounds
Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox
10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Property grounds
Hadley Amherst Location.Explore the Valley Colleges!

Hadley Amherst Location.Explore the Valley Colleges!

Hadley
10.0 out of 10, Exceptional, (132)
"Such a wonderful property and amazing host! A convenient location to the area as well as shopping and beautiful bike/walking trail!Thank you Colleen!"
United States
John M.
Hadley Amherst Location.Explore the Valley Colleges!
Terrace/patio
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough
10.0 out of 10, Exceptional, (6)
"Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! "
United States
Cindy B.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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, (142)
"We enjoyed our stay in this beautiful old farmhouse. Plenty of room for everyone and kitchen and linens were fully stocked."
United States
Nicole K.
The price is HK$1,150
HK$2,357 total
includes taxes & fees
17 Nov - 18 Nov
Big farmhouse in the foothills of the Berkshires
Exterior
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, (33)
"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.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis
8.6 out of 10, Excellent, (9)
"The house’s position on the water, being further out than all other surrounding homes, makes for beautiful views of the lake and all it activities. The sunrises are beautiful. Unfortunately when you don’t have proper running water and a toilet that flushes without having to put water in the tank almost every time, the experience is less than ideal. The host warned us of the toilet about 15 min before we arrived and never had the kitchen sink fixed in the 5 days we stayed. That was rather...
United States
Colleen W.
Private Island - Largest Fresh Water Reservoir in Mass
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

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

10/10 Excellent
"Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet."
Gloria 2-night trip
Posted 3 days ago
Quality Inn Westfield - 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:

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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 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?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Chester is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like The Bookstore, or get outside and enjoy nature at Glendale Falls. Chester Town Hall and Pyramid Lake 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.