Photo by Elizabeth Massa Peroulakis

Chester Holiday Rentals

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Holiday Rentals in Chester

Townhouse with Pool Table - Renovated w/ King Bed

10.0 out of 10, Exceptional, (6)
"The home was perfect for our crew while working out of town. Everything was as listed and Mabel was a great host and even called to make sure we were settled in and didn't need anything. "
The price is NZ$640
includes taxes & fees
4 Aug - 5 Aug
Townhouse with Pool Table - Renovated w/ King Bed

Cozy Home in Holyoke with 3 bedrooms

9.8 out of 10, Exceptional, (7)
"Wonderful stay. Veronica was so kind and super responsive. The house was a great size and have everything we needed. We stayed there with 2 adults and 2 toddlers under 3. It was plenty of space. And a great location to all the area had to offer, museums, fun restaurants in North Hampton, etc. Would definitely stay again. "
The price is NZ$636
includes taxes & fees
28 July - 29 July
Cozy Home in Holyoke with 3 bedrooms

Low-scent, historic, well-located, downtown house

10.0 out of 10, Exceptional, (4)
"It’s a beautiful home that worked for our stay as a family "
The price is NZ$1,212
includes taxes & fees
26 July - 27 July
Low-scent, historic, well-located, downtown house

Button's Modern Luxury Walkup Downtown Northampton

The price is NZ$840
includes taxes & fees
16 July - 17 July
Button's Modern Luxury Walkup Downtown Northampton

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (138)
"The house is so charming. Beautifully decorated and very clean, with everything you could need easy to find. Plenty of space for 8 people. The hosts are very helpful and communicative. Would definitely stay here again."
The price is NZ$598
includes taxes & fees
27 July - 28 July
Big farmhouse in the foothills of the Berkshires

Home in the Woods

10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
The price is NZ$535
includes taxes & fees
14 July - 15 July
Home in the Woods

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
The price is NZ$2,474
includes taxes & fees
15 July - 16 July
Charming 3-bedroom Modern cottage with lakeside views

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

10.0 out of 10, Exceptional, (5)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is NZ$829
includes taxes & fees
6 Aug - 7 Aug
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

The price is NZ$673
includes taxes & fees
28 July - 29 July
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

10.0 out of 10, Exceptional, (3)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
The price is NZ$917
includes taxes & fees
16 July - 17 July
Hummingbird Haven is a Berkshires retreat surrounded by nature and local charm.

Spacious 5-bedroom house in charming Lee with WiFi

The price is NZ$1,658
includes taxes & fees
12 Aug - 13 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (252)
"One of the best properties i've ever stayed at "
The price is NZ$487
includes taxes & fees
31 July - 1 Aug
Berkshire Village Carriage House - Super Private!!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is NZ$1,102
includes taxes & fees
4 Aug - 5 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Experience Timeless Elegance in The Edith Wharton Room!

The price is NZ$586
includes taxes & fees
14 July - 15 July
Experience Timeless Elegance in The Edith Wharton Room!

Cozy Carriage House room with a double bed and private balcony

The price is NZ$655
includes taxes & fees
14 July - 15 July
Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is NZ$689
includes taxes & fees
14 July - 15 July
Historic Susan B. Anthony Room - Cozy & Charming Stay

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is NZ$807
includes taxes & fees
21 July - 22 July
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is NZ$1,012
includes taxes & fees
14 July - 15 July
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Elegant suite with a king bed, fireplace, and kitchenette.

The price is NZ$910
includes taxes & fees
21 July - 22 July
Elegant suite with a king bed, fireplace, and kitchenette.
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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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?

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. : This holiday home rental outside of Chester offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.