Chester Vacation Rentals

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Vacation 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 CA $119
CA $136 total
includes taxes & fees
Aug 21 - Aug 22
Oakhill Pines Campground

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (6)
"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 CA $302
CA $379 total
includes taxes & fees
Aug 27 - Aug 28
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, (22)
"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 CA $180
CA $237 total
includes taxes & fees
Sep 15 - Sep 16
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, (121)
"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, (104)
"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

6.0 out of 10, (2)
"Washrooms could be cleanier and larger. Also improve stability of the washrooms."
The price is CA $120
CA $196 total
includes taxes & fees
Aug 21 - Aug 22
Spruce Bell Tent near Peggy's Cove

Ocean front cottage in the heart of Hubbards.

9.8 out of 10, Exceptional, (49)
"Excellent week with the kids. Hosts were great. "
Ocean front cottage in the heart of Hubbards.

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

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

10.0 out of 10, Exceptional, (29)
"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, (81)
"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, (94)
"We enjoyed our stay. The location was perfect for visiting Mahone Bay. "
One bedroom fully equipped Mahone Bay luxury cottage

Unique Ocean View Hilltop Retreat

10.0 out of 10, Exceptional, (170)
"This is our third stay and we thoroughly enjoyed ourselves as always. The property is fantastic for a group stay and has everything you need for a weekend away. "
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

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

Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!

10.0 out of 10, Exceptional, (28)
"This is the best property we got over that past decade!! The location is just amazing with a breathtaking view on the bay. The cottage is equipped like never seen before with a level of details that is over the top! The cleanliness and the condition of the place is 11/10 and the communication with the owner Beth is irreproachable. I do recommend this place to whoever wants to spend good, relaxing and quiet time in a peaceful environment. "
Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!

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

10.0 out of 10, Exceptional, (92)
"Beautiful location, delightful merchants and lovely hosts."
Located in the heart of Peggys Cove! Featured in Saltscapes Atlantic magazine!

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!

Conveniently located in the centre of the South Shore. Close to everything

The price is CA $135
CA $237 total
includes taxes & fees
Aug 21 - Aug 22
Conveniently located in the centre of the South Shore. Close to everything
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

Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals close to the most popular sights in Chester, or you can choose a secluded option if you'd like a relaxing place to stay. Chester is known for its golf courses and theaters. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best vacation rentals in Chester?

Family Home In the Heart of the Village of Chester: Visitors give good reviews to this Chester vacation home rental, which is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

How many vacation rentals will I find in Chester?

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

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 vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.