A large, two-story house with a steeply pitched roof and a chimney.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester vacation rentals

A wooden deck with a hot tub surrounded by trees.

1. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Windsor Road
10.0 out of 10, Exceptional, (16 reviews)
"The cleanliness was impeccable, the hospitality was lovely. Everything one needs while away from home was supplied and then some ! Would definitely visit again !"
Canada
Carol
$161 nightly
The price is $183
Oct 19 - Oct 20
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A bedroom with a wooden ceiling, a bed with white bedding, a nightstand, a dresser, a chair, a window with a view of trees, and a patterned rug.

2. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (89 reviews)
"It was a cute and cozy stay. We would stay here again."
Canada
Julie
$258 nightly
The price is $294
Oct 19 - Oct 20
Total with taxes and fees
Black Forest Cabins
A small cabin with a deck, a door, and a window.

3. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
10.0 out of 10, Exceptional, (23 reviews)
"Hot tub is Devine, everything is clean and thoughtfully provided. Basket of snacks was a sweet treat! We enjoyed the large deck and privacy very much ♥️we will definitely be back "
Canada
Suzanne
$161 nightly
The price is $184
Oct 18 - Oct 19
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A bright living room with a white sofa, a coffee table, and a potted plant.

4. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (118 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
One bedroom fully equipped Mahone Bay luxury cottage
A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

5. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (114 reviews)
"Comfortable cottage very close to town centre but also quiet and calm."
Canada
Richard
$207 nightly
The price is $236
Oct 20 - Oct 21
Total with taxes and fees
Mahone Bay Hide-Away
A wooden building with a sign reading "The Knot."

6. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
$130 nightly
The price is $148
Oct 20 - Oct 21
Total with taxes and fees
Red Barn Bed & Breakfast
A view of a waterfront property with a dock and a small building.

7. Oceanfront Luxury with Magical Views of Sunset and Sunrise

Oceanfront Luxury with Magical Views of Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (28 reviews)
"Beautiful spot!"
United States
Kirby D.
$306 nightly
The price is $357
Oct 20 - Oct 21
Total with taxes and fees
Oceanfront Luxury with Magical Views of Sunset and Sunrise
A small, two-story cabin with a deck, large windows, and a fireplace.

8. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
9.8 out of 10, Exceptional, (17 reviews)
"Amenities are fantastic, very private"
Canada
francesco c.
$161 nightly
The price is $184
Oct 20 - Oct 21
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A sunset view through a window with bare trees and a distant shoreline.

9. 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Hubbards
8.6 out of 10, Excellent, (61 reviews)
"We enjoyed our stay. Property was as described, we especially enjoyed the view."
United States
Sandy e.
$147 nightly
The price is $168
Oct 22 - Oct 23
Total with taxes and fees
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
A calm lake with boats docked at the pier, surrounded by trees.

10. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.4 out of 10, Exceptional, (14 reviews)
"Really enjoyed our stay at the cottage. Was warm and cozy for the duration of our stay. It was so enjoyable that we changed our plans to tour around and stayed at the cottage. Beautiful location."
Canada
Harold
$208 nightly
The price is $238
Oct 18 - Oct 19
Total with taxes and fees
Lake Mushamush Cottage!
A staircase with wooden balusters and a handrail, leading to a landing with a red door.

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

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
Lunenburg
9.0 out of 10, Wonderful, (14 reviews)
"Loved our stay. Nice and clean, quiet and peaceful. Amazing yard. Basics were excellent (Bed, Tv & facilities). Definitely recommend."
Canada
Patrick
$196 nightly
The price is $223
Nov 2 - Nov 3
Total with taxes and fees
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
A dock with boats, a clear blue lake, and a forested island.

12. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.8 out of 10, Exceptional, (7 reviews)
"Fantastic property, location, and hosts. Will be booking again!"
Canada
Josh
$242 nightly
The price is $276
Nov 2 - Nov 3
Total with taxes and fees
Mermaid's Retreat - Caribou Lake Cottage!
A sandy beach with people walking along the shore.

13. Downtown Bridgewater Suite near River and Trails

Downtown Bridgewater Suite near River and Trails
Bridgewater
9.4 out of 10, Exceptional, (3 reviews)
"This property was comfortable and convenient and we enjoyed our stay here."
United States
Marty
$110 nightly
The price is $126
Oct 18 - Oct 19
Total with taxes and fees
Downtown Bridgewater Suite near River and Trails
A beach with clear water, a sandy shore, and a forested island in the distance.

14. Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
Ingramport
9.8 out of 10, Exceptional, (122 reviews)
"Great location and beautiful spot. Our family of 5 really enjoyed our visit!!"
United States
Victoria W.
$308 nightly
The price is $361
Oct 18 - Oct 19
Total with taxes and fees
Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
A wooden cabin in a snowy forest.

15. Pet-Friendly Glamping Dome close to Peggy’s Cove!

Pet-Friendly Glamping Dome close to Peggy’s Cove!
Seabright
10.0 out of 10, Exceptional, (19 reviews)
"Great place and location and the owners were very helpful!"
Canada
Judy
$209 nightly
The price is $244
Nov 9 - Nov 10
Total with taxes and fees
Pet-Friendly Glamping Dome close to Peggy’s Cove!
A sauna with a view of the sea, wooden walls, and a stone heater.

16. Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
Boutiliers Point
9.6 out of 10, Exceptional, (27 reviews)
"Check in staff were very friendly and showed us around the cabin and facilities. Cabin was clean, had all required items for cooking and enjoying the stay."
United States
Kristopher H.
$187 nightly
The price is $218
Oct 22 - Oct 23
Total with taxes and fees
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
A small white cabin with green trim and a porch, surrounded by greenery.

17. Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.2 out of 10, Good, (7 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
$203 nightly
The price is $236
Oct 18 - Oct 19
Total with taxes and fees
Orchard Cabin #4 - Hubbards Beach
A tented accommodation with a bed, two chairs, and a view of a lake.

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

Luxury lakefront dome with private beach, close to nature and town!
Lunenburg
10.0 out of 10, Exceptional, (41 reviews)
"This place exceeded expectations and was an absolute delight."
Canada
Sandie
$264 nightly
The price is $300
Nov 2 - Nov 3
Total with taxes and fees
Luxury lakefront dome with private beach, close to nature and town!
A porch with colorful Adirondack chairs and a wooden deck.

19. Log Cabin #1 - Hubbards Beach

Log Cabin #1 - Hubbards Beach
Hubbards
9.8 out of 10, Exceptional, (6 reviews)
"Nothing else to add."
Canada
Blair
$330 nightly
The price is $385
Oct 18 - Oct 19
Total with taxes and fees
Log Cabin #1 - Hubbards Beach
A living room with a sofa, a table with a plant, and a window with blinds.

20. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Bridgewater
8.6 out of 10, Excellent, (14 reviews)
"A little hard to find as it is not well marked, although the actual unit was great. Clean and had everything we needed for our stay. Centrally located and easy to get where we needed. Would definitely stay again if in the area."
Canada
Alan
$202 nightly
The price is $236
Oct 20 - Oct 21
Total with taxes and fees
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
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

The Homeport Motel

The Homeport Motel

10/10 Excellent
"Nous avons décidé de prolonger notre séjours en renouvelant notre réservation!"
nathalie 1-night trip
Posted 13 hours ago
The Homeport Motel

Find out more about Chester

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 $168 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.

Explore a world of travel with Expedia

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?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This vacation home rental outside 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Chester?

Choose from 16 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. Chester Art Center 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.