Chester Holiday Rentals

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Holiday Rentals in Chester

Family Home In the Heart of the Village of Chester

9.6 out of 10, Exceptional, (28)
"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."
Family Home In the Heart of the Village of Chester

Oakhill Pines Campground

3.0 star property
9.2 out of 10, Wonderful, (9)
"Great place"
The price is AU$151
includes taxes & fees
31 Aug - 1 Sept
Oakhill Pines Campground

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (9)
"Beautiful quiet cabins with local trails to enjoy and explore. The sauna was fantastic and we loved the decor! So easy to access our room. Highly recommend!"
The price is AU$428
includes taxes & fees
1 Sept - 2 Sept
Black Forest Cabins

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

8.0 out of 10, Very good, (23)
"The property is as we have expected. one of the additional benefits are the board games and card games provided. Kids just love them."
The price is AU$267
includes taxes & fees
8 Sept - 9 Sept
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

9.8 out of 10, Exceptional, (122)
"We loved Whaleback Cottage! It was very comfortable and clean with incredible views! Tom and Donna were great hosts! We would definitely stay there again."
Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (105)
"Property was wonderful, love Lunenburg and area would definitely return!!!"
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Juniper Bell Tent near Peggy's Cove

9.0 out of 10, Wonderful, (2)
"Overall very comfortable and clean. Comfortable inside the tent and patio nice and big. Small shared outdoor bathroom and no outdoor sink to do dishes. Enjoyed our stay."
The price is AU$228
includes taxes & fees
1 Sept - 2 Sept
Juniper Bell Tent near Peggy's Cove

Spruce Bell Tent near Peggy's Cove

6.0 out of 10, (2)
"Washrooms could be cleanier and larger. Also improve stability of the washrooms."
The price is AU$228
includes taxes & fees
1 Sept - 2 Sept
Spruce Bell Tent near Peggy's Cove

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

9.6 out of 10, Exceptional, (31)
"We loved the privacy and view of ocean. Loved watching the tide go in and out, that was so amazing. Missed having a sandy beach to walk on. Otherwise , fantastic. Golf course restaurant was amazing as well. "
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Ocean front cottage in the heart of Hubbards.

9.8 out of 10, Exceptional, (50)
"Excellent week with the kids. Hosts were great. "
Ocean front cottage in the heart of Hubbards.

Moonlight Cottage

9.8 out of 10, Exceptional, (12)
"Loved getting to come stay at the house that was the Grey Gull on Haven the TV show! The host was great with communicating and our stay was awesome."
Moonlight Cottage

The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

9.8 out of 10, Exceptional, (220)
"We had an absolutely wonderful time on the Land Yacht, the kids used the pool everyday and we all thoroughly enjoyed the perfect weather from the solarium :) The Land Yacht in an incredible spot and we will definitely be back again."
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

Located in the heart of Peggys Cove! Featured in Saltscapes Atlantic magazine!

10.0 out of 10, Exceptional, (93)
"Beautiful location, delightful merchants and lovely hosts."
Located in the heart of Peggys Cove! Featured in Saltscapes Atlantic magazine!

Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

10.0 out of 10, Exceptional, (31)
"They thought of everything. It was great"
Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

Mahone Bay Hide-Away

10.0 out of 10, Exceptional, (83)
"This was a gem of an accommodation! It was beautifully decorated and designed with all sorts of tasteful decor items but there was a ton of storage space for all of our needs. They had everything it was so well equipped, nothing was missed in the design and layout. It was just as comfortable as it was aesthetically beautiful. We give this a 10 out of 10!"
Mahone Bay Hide-Away

One bedroom fully equipped Mahone Bay luxury cottage

10.0 out of 10, Exceptional, (98)
"I really appreciated having the washer and dryer in the unit. It was walkable to all areas in Mahone Bay."
One bedroom fully equipped Mahone Bay luxury cottage

Unique Ocean View Hilltop Retreat

10.0 out of 10, Exceptional, (170)
"Great house with tonnes of character, the hosts answered all questions we had and had good communication!"
Unique Ocean View Hilltop Retreat

Amazing ocean view/ private road/close to bayswater beach.

8.6 out of 10, Excellent, (44)
"We enjoyed the location and house. Made a great place to stay on the water near Peggy’s Cove and Lunenburg."
Amazing ocean view/ private road/close to bayswater beach.

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

10.0 out of 10, Exceptional, (81)
"Everything about our trip and this property was amazing. The location, the peace, the scenery, etc. exceeded our expectations. The house was perfect and so comfortable. We hope to be back soon! "
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

Beautiful Lakefront Home with 5 Bed/3 Baths, WiFi, tons of amenities!

9.8 out of 10, Exceptional, (30)
"Great house with basics to make it easy to stay."
Beautiful Lakefront Home with 5 Bed/3 Baths, WiFi, tons of amenities!
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

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$151 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

Are there holiday rentals 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 golf courses and theatres. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best holiday rentals that Chester has to offer?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This holiday home rental outside of Chester is located by the ocean, and has a balcony, a garden and air conditioning to put you at ease 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 and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Chester?

Choose from 13 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Cultural attractions to visit include Chester Playhouse and Lordly House Museum. Tancook Island and Chester Golf Club are other places to visit while you're in town.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.