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, (26)
"The property was large and very spacious. It was clean and comfortable. The house is near the water and close to town. We stayed here for a work conference, and it was nice for everyone to have their own space. "
Family Home In the Heart of the Village of Chester

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (3)
"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 NZ$438
includes taxes & fees
11 Aug - 12 Aug
Black Forest Cabins

Oakhill Pines Campground

3.0 star property
6.0 out of 10, (1)
"It was ok but I found it very expensive for only 1 plug in and no shower. I did like the location and staff were very friendly. "
The price is NZ$166
includes taxes & fees
27 July - 28 July
Oakhill Pines Campground

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (94)
"Property was wonderful, love Lunenburg and area would definitely return!!!"
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Spruce Bell Tent near Peggy's Cove

The price is NZ$238
includes taxes & fees
20 July - 21 July
Spruce Bell Tent near Peggy's Cove

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

Wilson's Coastal Club - C3

10.0 out of 10, Exceptional, (5)
"It's great when all goes well, but it's truly a blessing when things go wrong and your host takes care of you! Our hot water froze our first night and Jessica and Kyle were so lovely and helpful. Really enjoyed our stay and hope to come back again next year. "
The price is NZ$393
includes taxes & fees
21 July - 22 July
Wilson's Coastal Club - C3

Oceanfront 3-Bedroom Captain's House

10.0 out of 10, Exceptional, (18)
"Very clean, comfy, great water views. Recommended!"
Oceanfront 3-Bedroom Captain's House

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

7.8 out of 10, Good, (13)
"This property was great for our one night stay as a group attending a show at the shore club. The patio and view is wonderful! Owner was in contact very quickly which was very much appreciated. "
The price is NZ$288
includes taxes & fees
22 July - 23 July
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Moonlight Cottage

9.8 out of 10, Exceptional, (11)
"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

Luxury lakefront dome with private beach, close to nature and town!

Luxury lakefront dome with private beach, close to nature and town!

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

9.8 out of 10, Exceptional, (87)
"We loved the view, everything we needed was available and more. All our requests and concerns were answered immediately. All 🛌 were clean and comfortable."
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

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

9.8 out of 10, Exceptional, (28)
"Great house with basics to make it easy to stay."
Beautiful Lakefront Home with 5 Bed/3 Baths, WiFi, tons of amenities!

Oceanfront Luxury Magical Views Sunset and Sunrise

9.4 out of 10, Exceptional, (15)
"Short stay, unfortunately, but I’ll definitely be back. "
Oceanfront Luxury Magical Views Sunset and Sunrise

Wilson's Coastal Club - C2

10.0 out of 10, Exceptional, (2)
"Great cottage. Exactly as advertised - cozy furniture, lovely surroundings and gardens, easy parking. The beds are exceptionally comfy! Would stay again!"
The price is NZ$489
includes taxes & fees
24 July - 25 July
Wilson's Coastal Club - C2

Wilson's Coastal Club - C1

10.0 out of 10, Exceptional, (3)
"Amazing spot! Gorgeous location, staff really friendly and helpful and we had such a relaxing weekend. Highly recommend!"
Wilson's Coastal Club - C1

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

9.8 out of 10, Exceptional, (118)
"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

Apple Orchard Cottage Lunenburg, Nova Scotia, Canada

9.2 out of 10, Wonderful, (65)
"Close to Lunenburg, nice and quiet area. Small rocky beach 2 minutes across the street. Great views "
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

10.0 out of 10, Exceptional, (2)
"Wonderful studio, clean, comfortable bedOn 2nd floor (very quiet)Walkable to Lunenburg old town, restaurants & Bluenose marinaWalkable to Tim Hortons & Independent Grocery "
The price is NZ$446
includes taxes & fees
1 Aug - 2 Aug
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Ocean front cottage in the heart of Hubbards.

9.8 out of 10, Exceptional, (43)
"This place was perfect for our little family stay! We enjoyed watching the boats from the deck and theres lots to do in the area. The hosts are lovely :)"
Ocean front cottage in the heart of Hubbards.
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

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?

Family Home In the Heart of the Village of Chester: This highly rated holiday home rental in Chester is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

How many holiday rentals will I find in Chester?

Choose from 11 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.