Chester Holiday Rentals

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Top Holiday Rentals Destinations in Chester

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

9.6 out of 10, Exceptional, (34)
"Beautiful setting, very peaceful with lovely linens on the beds. The kitchen is fully stocked, the sitting room is comfortable and the outside decks are amazing. The little village of Chester was close by with a cozy pub offering live music on select nights and the local playhouse had local talent performing while we were there. We would stay again"
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Moonlight Cottage

9.2 out of 10, Wonderful, (15)
"Great time, went Peggy’s cove, Hubbard farm market, lunenburg and mahone bay"
Moonlight Cottage

Oceanfront Luxury Magical Views Sunset and Sunrise

9.6 out of 10, Exceptional, (18)
"We took day trips from Holly’s home all week, but the view off the balcony was a delight to return to. "
Oceanfront Luxury Magical Views Sunset and Sunrise

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

8.4 out of 10, Very good, (27)
"Beautiful view, the property owner was very responsive, they even had water in the fridge. Was perfect for our relaxing family getaway! "
The price is NZ$291
includes taxes & fees
15 Oct - 16 Oct
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

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

8.6 out of 10, Excellent, (46)
"Great property for a quiet get away"
Amazing ocean view/ private road/close to bayswater beach.

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

10.0 out of 10, Exceptional, (98)
"We had a wonderful time. You can’t beat the views!"
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Spectacular Oceanfront Living in Authentic Fishing Village

10.0 out of 10, Exceptional, (110)
"A family member was getting married in Hubbards this weekend and we were her decorating crew so needed somewhere to stay. The house was perfect it slept all 13 of us (10 adults, 3 little kids), it was clean, well maintained and had absolutely stunning views. Kelly was absolutely wonderful to deal with, we will definitely be back! "
Spectacular Oceanfront Living in Authentic Fishing Village

Stunning Ocean Front cottage, minutes from the beach

10.0 out of 10, Exceptional, (28)
"This property was clean, well stocked with items we would need, had a fabulous view the water. The host was very friendly and quick to respond. We had an amazing stay and would highly recommend this property if you are looking for some relaxation yet still driveable to tourist spots (1 hour +/-)."
Stunning Ocean Front cottage, minutes from the beach

Cozy Oceanfront Escape with Hot Tub

10.0 out of 10, Exceptional, (20)
"Clean, well appointed rooms with an amazing view of the ocean. The owners are very considerate of traveller’s, with the amenities offered in the home. The Kitchen is stocked with quality items. A very pleasurable stay!"
Cozy Oceanfront Escape with Hot Tub

Oakhill Pines Campground

3.0 star property
9.0 out of 10, Wonderful, (16)
"Great place"
Oakhill Pines Campground

Black Forest Cabins

3.0 star property
9.8 out of 10, Exceptional, (10)
"Great spot for a special night out … beds were super comfortable "
The price is NZ$344
includes taxes & fees
2 Nov - 3 Nov
Black Forest Cabins

Basement Studio w/Den & Kitchenette

9.2 out of 10, Wonderful, (5)
"Was clean and they were very helpful. "
The price is NZ$279
includes taxes & fees
6 Oct - 7 Oct
Basement Studio w/Den & Kitchenette

Juniper Bell Tent near Peggy's Cove

8.8 out of 10, Excellent, (3)
"Good for a nights stay and close to Peggy’s cove. Comfy and enough space"
The price is NZ$249
includes taxes & fees
6 Oct - 7 Oct
Juniper Bell Tent near Peggy's Cove

Cute n Lovely

6.8 out of 10, (3)
"The property was very clean and had everything we need and the location was great. Only issue with it being a lower apartment we found at times and sometimes early in morning children were loud. "
The price is NZ$424
includes taxes & fees
6 Oct - 7 Oct
Cute n Lovely

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (111)
"I wish we had more time to enjoy the cottage. There was so much to see in area, we were busy all day, but a comfy place to come home too. "
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!

9.4 out of 10, Exceptional, (6)
"The host was very pleasant and helpful..the room was immaculate and very nice...location was peaceful and quiet, but not too far from stores and restaurants "
The price is NZ$283
includes taxes & fees
1 Nov - 2 Nov
Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!

One bedroom fully equipped Mahone Bay luxury cottage

10.0 out of 10, Exceptional, (101)
"Great cottage to use as a base to discover the area. Well equipped, quiet and close to restaurants and shopping."
The price is NZ$336
includes taxes & fees
13 Oct - 14 Oct
One bedroom fully equipped Mahone Bay luxury cottage

This quiet neighbourhood is great place to relax and enjoy the peace and quiet.

10.0 out of 10, Exceptional, (2)
"This property worked out very well for our work trip (3-4 staff members) over a 10 day periord. Host was easy to deal with and fast to reply to messages. Would stay here again. "
The price is NZ$1,274
includes taxes & fees
13 Oct - 14 Oct
This quiet neighbourhood is great place to relax and enjoy the peace and quiet.

Peaceful Retreat on Schmidt Lake

10.0 out of 10, Exceptional, (2)
"We had an amazing time at this property, its the perfect property for a summer get away. The hosts responded promptly and check in was seamless."
The price is NZ$1,624
includes taxes & fees
6 Oct - 7 Oct
Peaceful Retreat on Schmidt Lake

Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

10.0 out of 10, Exceptional, (3)
"Beautiful location on the water, super friendly hosts. Location close to so many little towns with great food and amazing people. Trailer has everything that you need for your stay, they thought of everything. They made us feel welcome and we will be back for sure. We took our paddleboards out; he even lent us a fishing rod to use on the nearby Warf. "
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck
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 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$249 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia