Chester Vacation Rentals

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Vacation Rentals in Chester

1800' | Front HBR | DT 5 Min Walk | Water views
Smart TV, fireplace, table tennis, books
1800' | Front HBR | DT 5 Min Walk | Water views
10.0 out of 10, Exceptional, 1 review
"Great location and easy access to restaurants, shops. Bed was quite comfortable."
1800' | Front HBR | DT 5 Min Walk | Water views
One bedroom fully equipped Mahone Bay luxury cottage
Fridge, microwave, oven, stovetop
One bedroom fully equipped Mahone Bay luxury cottage
10.0 out of 10, Exceptional, 70 reviews
"Fantastic amenities, beautifully decorated, very functional living space for extended stays private barbecue area, lovely front porch, easy access. Owners are great and easy communicators."
One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay Hide-Away
TV
Mahone Bay Hide-Away
10.0 out of 10, Exceptional, 50 reviews
"We would definitely choose this place again if we stay in Mahone Bay again. It was very clean, well kept and adorable. Kitchen was fully functional. Small, but perfect for a couple on a romantic getaway, or a couple with a small child. My only slightly negative comment is that the bed is a queen, not a king, and the listing does not specify the size of bed. But that's just a very minor point and I would still stay here again."
Mahone Bay Hide-Away
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Oceanfront 2BR Private Apartment
Property grounds
Oceanfront 2BR Private Apartment
9.8 out of 10, Exceptional, 46 reviews
"Beautiful location, terrific host, very comfortable"
Oceanfront 2BR Private Apartment
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Aerial view
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
9.8 out of 10, Exceptional, 68 reviews
"So restful and an astoundingly gorgeous location. Couldn't be happier with the stay, the house, the area, and Phil gave such good advice! We had a glitch with the stove (our problem, not the stove) and he popped over to straighten us out in a flash. Finding the place in the dark was a bit of a challenge; if you have cell coverage, it should be fine. Otherwise, it is wise to examine a map very carefully before you set off (in the dark)."
The price is $302
$397 total
includes taxes & fees
Jun 29 - Jun 30
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Knotting Hill - Escape to tranquility & charm
Property grounds
Knotting Hill - Escape to tranquility & charm
Knotting Hill - Escape to tranquility & charm
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
Fridge, microwave, oven, stovetop
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
10.0 out of 10, Exceptional, 61 reviews
"What a beautiful cottage to enjoy during a rainy stay. We saw deer galore, coyotes, and a raccoon on our way. Everything we needed and more was abundantly available."
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
Beautiful Home on Sunny Acreage w/full bath & nearby ocean
Exterior
Beautiful Home on Sunny Acreage w/full bath & nearby ocean
10.0 out of 10, Exceptional, 3 reviews
"Short but good"
The price is $131
$200 total
includes taxes & fees
Jun 12 - Jun 13
Beautiful Home on Sunny Acreage w/full bath & nearby ocean
Romantic, oceanfront, renovated luxury cottage at a beach and near Halifax
Romantic, oceanfront, renovated luxury cottage at a beach and near Halifax
10.0 out of 10, Exceptional, 79 reviews
"It was close to Halifax, so catching our plane home was easy"
Romantic, oceanfront, renovated luxury cottage at a beach and near Halifax
Serenity Tiny House Cottage in Chester
Property grounds
Serenity Tiny House Cottage in Chester
10.0 out of 10, Exceptional, 51 reviews
"Sandra and Bill are fantastic hosts, who have built and outfitted this tiny home with such thoughtfulness and intention, that it was very difficult to bid it goodbye. The Southern Shore of Nova Scotia is one of the most beautiful- and friendliest - places I have ever been. Im counting down the days until I can visit next. Or retire here."
Serenity Tiny House Cottage in Chester
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada
Exterior
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada
9.2 out of 10, Wonderful, 55 reviews
"A beautiful old warm Character home in an absolutely stunning setting. If you want to experience staying on the South Shore this is a gem."
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada
Oceanside Vacation Cottage
Property grounds
Oceanside Vacation Cottage
9.4 out of 10, Exceptional, 19 reviews
"Everything described by previous renters was perfectly accurate and as advertised.. Our stay was exceptional. The location was so very relaxing and there was nothing that we could have wanted or needed. The hosts were very accommodating and we felt very welcomed. The fire pit overlooking the water was so much enjoyed by us. We will be back!!"
Oceanside Vacation Cottage
Entire house, Bridgewater. 2 Bedrooms, sleeps 4, 1.5 baths
Beach nearby, beach towels
Entire house, Bridgewater. 2 Bedrooms, sleeps 4, 1.5 baths
10.0 out of 10, Exceptional, 66 reviews
"Everything about the property was wonderful - quiet location, exceptionally clean home, lovely decor, very comfortable beds, every amenity needed to enjoy home away. Highly recommend."
Entire house, Bridgewater. 2 Bedrooms, sleeps 4, 1.5 baths
On the Beautiful South Shore Near Chester and Hubbards, Ns
Beach
On the Beautiful South Shore Near Chester and Hubbards, Ns
10.0 out of 10, Exceptional, 72 reviews
"If you are considering staying on the South Shore this property is highly recommended. Everything from start to finish was perfect. It is in a beautiful cove with lovely views from the terrace. Perfect for morning coffee or late evening drinks. The house was clean , spacious and well maintained. It was very well equipped with all household items and amenities. We enjoyed day trips to Luneberg, Mahone Bay and Peggy’sCove as well as shorter jaunts to Chester and Hubbards. Communication with the...
On the Beautiful South Shore Near Chester and Hubbards, Ns
Spectacular Oceanfront Living in Authentic Fishing Village
Terrace/patio
Spectacular Oceanfront Living in Authentic Fishing Village
10.0 out of 10, Exceptional, 88 reviews
"Great space lots of room! Host always available"
Spectacular Oceanfront Living in Authentic Fishing Village
Mahone Bay Town Center 2 Bedroom Apt. - Access to Grocery, Shops, Food and Fun
Outdoor dining
Mahone Bay Town Center 2 Bedroom Apt. - Access to Grocery, Shops, Food and Fun
9.8 out of 10, Exceptional, 14 reviews
"Everything was perfect with our stay."
Mahone Bay Town Center 2 Bedroom Apt. - Access to Grocery, Shops, Food and Fun
Right in the heart of Peggys Cove! Featured in Atlantic magazine!
Smart TV, fireplace, books
Right in the heart of Peggys Cove! Featured in Atlantic magazine!
10.0 out of 10, Exceptional, 76 reviews
"We had such a wonderful time at this wonderful, lovely cottage by the sea. We loved the historic charm of this beautiful home! Claire is the kindest, friendliest, most helpful host ever! The location is outstanding and the view out of every window looks like a picture postcard. Peggy's Cove is the quintessential seaside fishing village and we loved every minute of our time there. We would love to come back and stay again!"
Right in the heart of Peggys Cove! Featured in Atlantic magazine!
The Lookout Cottage - Private, ocean view home
Property grounds
The Lookout Cottage - Private, ocean view home
10.0 out of 10, Exceptional, 23 reviews
"Good stay. This place looks brand new inside. It's a. outside of town 15 min but if you are looking for a nice, peaceful, clean location, look no further."
The price is $275
$432 total
includes taxes & fees
Jun 17 - Jun 18
The Lookout Cottage - Private, ocean view home
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
Outdoor dining
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
9.8 out of 10, Exceptional, 118 reviews
"The area of the property was great able to look out over the bay from bedroom window and nice places not very far away its worththe stay"
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
Writer's Retreat: Privacy within sight and sound of the sea
Fridge, microwave, oven, stovetop
Writer's Retreat: Privacy within sight and sound of the sea
9.8 out of 10, Exceptional, 32 reviews
"This was our third time staying at Rosalie's cottage and it was as lovely as ever."
Writer's Retreat: Privacy within sight and sound of the sea
Don't see what you're looking for?
See all available properties in Chester
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.

Chester Vacation Rental Travel Info

Popular accommodation
Chester private vacation homes
Known landmarks
Chester Playhouse, Bayswater Beach Provincial Park and Lordly House Museum
International airport
Halifax, NS (YHZ-Stanfield Intl.)

Other types of properties in Chester you may be interested in

1800' | Front HBR | DT 5 Min Walk | Water views
Smart TV, fireplace, table tennis, books
1800' | Front HBR | DT 5 Min Walk | Water views
10.0 out of 10, Exceptional, 1 review
"Great location and easy access to restaurants, shops. Bed was quite comfortable."
1800' | Front HBR | DT 5 Min Walk | Water views
Rum Runner Inn
Oceanfront Honeymoon King Room with Sunporch | Water view
Rum Runner Inn
4.0 star property
9.0 out of 10, Wonderful, 778 reviews
"Great, romantic place for couples to stay with wonderful view "
The price is $109
$126 total
includes taxes & fees
Jun 2 - Jun 3
Rum Runner Inn
Days Inn & Conference Center by Wyndham Bridgewater
Suite, 1 King Bed, Non Smoking (One-Bedroom) | Desk, free cribs/infant beds, rollaway beds, free WiFi
Days Inn & Conference Center by Wyndham Bridgewater
2.5 star property
7.4 out of 10, Good, 977 reviews
"It was conveniently located and the service was excellent."
The price is $120
$138 total
includes taxes & fees
Jun 18 - Jun 19
Days Inn & Conference Center by Wyndham Bridgewater
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.

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $131 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation 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 vacation.

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 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?

Private Island, Ocean Front, Aspotogan Pennisula, South Shore Nova Scotia: This vacation home rental outside of Chester is located on the beach and has a fireplace, a patio, and laundry facilities to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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.

Recent reviews of Chester properties
Expedia verified reviews

Smugglers Cove Inn

Smugglers Cove Inn

5/5 Excellent
Would stay again
"Great service, well located, clean and quiet."
A verified traveler stayed at Smugglers Cove Inn
Posted 3 days ago
Smugglers Cove Inn