Chester Holiday Rentals

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Top cities in Chester

Vacation Rentals

East Chester

East Chester

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chester holiday rentals

A bedroom with a wooden ceiling, a bed with white bedding, a nightstand, a dresser, a chair, a window with a view of trees, and a patterned rug.

1. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (89 reviews)
"It was a cute and cozy stay. We would stay here again."
Canada
Julie
The price is NZ$337
includes taxes & fees
11 Nov - 12 Nov
Black Forest Cabins
A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.

2. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,337 reviews)
"We had a wonderful stay in Wolfville! The room was comfortable, clean, and welcoming, and the location made it easy to explore the area. We really enjoyed our time here and appreciated the overall experience. We would happily stay here again and recommend it to anyone visiting Wolfville!"
Canada
Ernesto
The price is NZ$271
includes taxes & fees
7 Dec - 8 Dec
Micro Boutique Living Wolfville
A compact living space with a bed, a TV on a stand, two chairs, a small table with a vase, and a patterned rug.

3. Your Another Family Home

Your Another Family Home
2.0 star property
Beechville
The price is NZ$196
includes taxes & fees
11 Nov - 12 Nov
Your Another Family Home
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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Find holiday rentals that suit your style

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Apartments
Apartments
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Aparthotels
Aparthotels

Top Chester Hotel Reviews

A pathway leading to a house surrounded by lush greenery and a well-maintained garden.
Miller House By the Bay

Miller House By the Bay

Miller House By the Bay
mahone bay

10/10 Excellent

Miller House is a gorgeous and warm place to stay in the absolutely beautiful Mahone Bay. The host is marvellous, treating guests as family and engaging in tremendously interesting conversation while preparing fabulous breakfasts. I felt utterly welcome and at home in this beautiful house which faces the bay, and would come back tomorrow if Australia wasn’t so far away!
Australia
Margaret
Reviewed September 22, 2026
Miller House By the Bay

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 favorite 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 depends 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 NZ$235 per night. Entering your travel dates in the search wizard you might find 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.