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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chester vacation rentals

Premium bedding, pillowtop beds, WiFi (free)

1. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (67 reviews)
"A very lovely weekend getaway from my partner and I. Great location to go between Mahone Bay, Lunenburg and Bridgewater. Communication was very good. Really enjoyed our stay."
Canada
Jacob
$231 nightly
The price is $263
Aug 25 - Aug 26
Total with taxes and fees
Black Forest Cabins
Outdoor spa tub

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

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Windsor Road
9.8 out of 10, Exceptional, (10 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
$164 nightly
The price is $187
Aug 30 - Aug 31
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Cabin, 1 Double Bed, Shared Bathroom | Desk, WiFi (free)

3. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
8.8 out of 10, Excellent, (23 reviews)
"Staff was super welcoming and cabin was all set for us! "
Canada
Andrea
$84 nightly
The price is $95
Aug 13 - Aug 14
Total with taxes and fees
Oakhill Pines Campground
Exterior detail

4. 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, (16 reviews)
"Amenities are fantastic, very private"
Canada
francesco c.
$164 nightly
The price is $187
Aug 14 - Aug 15
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
View from property

5. 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
8.4 out of 10, Very Good, (43 reviews)
"Have use of all the facilities (laundry) was extremely helpful when travelling with a toddler."
Canada
Lisa
$181 nightly
The price is $207
Sep 9 - Sep 10
Total with taxes and fees
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
TV

6. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (111 reviews)
"It was perfect. Very relaxed stay close to town. Thanks"
Canada
James
$234 nightly
The price is $267
Aug 27 - Aug 28
Total with taxes and fees
One bedroom fully equipped Mahone Bay luxury cottage
Interior

7. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (62 reviews)
"Immaculately clean and cozy! We had a lovely stay."
United States
Kathryn H.
$234 nightly
The price is $267
Aug 16 - Aug 17
Total with taxes and fees
One bedroom fully equipped Mahone Bay luxury cottage
Interior

8. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (107 reviews)
"Close to restaurants, sights, many walking distance. Clean, bright, lodgings. Welcoming and helpful hosts. Would recommend to anyone "
Canada
Nancy R.
$192 nightly
The price is $219
Aug 13 - Aug 14
Total with taxes and fees
Mahone Bay Hide-Away
Exterior detail

9. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
$172 nightly
The price is $196
Aug 26 - Aug 27
Total with taxes and fees
Red Barn Bed & Breakfast
Property grounds

10. Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore
9.6 out of 10, Exceptional, (22 reviews)
"Beautiful spot!"
United States
Kirby D.
$471 nightly
The price is $550
Aug 12 - Aug 13
Total with taxes and fees
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Marina

11. Ocean Sanctuary - The Salty Cribb Cabin

Ocean Sanctuary - The Salty Cribb Cabin
Rose Bay
10.0 out of 10, Exceptional, (2 reviews)
"When we arrived after a long trip we found the rooms were clean, welcoming and attractive. The cabin was well equipped and everything worked. Beautiful location, always enjoyed the drive up to Lunenberg."
United States
Paul K.
Ocean Sanctuary - The Salty Cribb Cabin
Exterior

12. Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.4 out of 10, Good, (6 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
$223 nightly
The price is $260
Aug 18 - Aug 19
Total with taxes and fees
Orchard Cabin #4 - Hubbards Beach
Terrace/patio

13. Oceanfront Kayaking retreat close to Lunenburg

Oceanfront Kayaking retreat close to Lunenburg
Lunenburg
9.0 out of 10, Wonderful, (2 reviews)
"Place was really spacious, amazing living spaces and out of this world views. Access to kayaks was a great treat. Enjoyed location just outside of Lunenburg and lots to do. Unfortunately weren’t able to get the TV to work and some appliances were finicky to get operating though nothing that would keep us from coming back. The place had so much to offer and was a nice place for a relaxing weekend getaway!"
United States
Matthew P.
$304 nightly
The price is $346
Aug 18 - Aug 19
Total with taxes and fees
Oceanfront Kayaking retreat close to Lunenburg
Property grounds

14. KoKo Bay:GLAMPING: Where Glamour meets Nature! Mix of Hilton Hotel and Camping!

KoKo Bay:GLAMPING: Where Glamour meets Nature! Mix of Hilton Hotel and Camping!
Ingramport
10.0 out of 10, Exceptional, (2 reviews)
"A private oasis"
United States
Lisa Althea R.
$147 nightly
The price is $171
Sep 9 - Sep 10
Total with taxes and fees
KoKo Bay:GLAMPING: Where Glamour meets Nature! Mix of Hilton Hotel and Camping!
Beach nearby

15. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful spot we had the best time!!"
Canada
Patricia C.
$212 nightly
The price is $242
Aug 17 - Aug 18
Total with taxes and fees
Lake Mushamush Cottage!
Living area

16. 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
9.4 out of 10, Exceptional, (6 reviews)
"Great location for us and very clean and spacious."
Canada
Christina
$205 nightly
The price is $240
Aug 14 - Aug 15
Total with taxes and fees
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Property grounds

17. 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, (10 reviews)
"Amazing place! Very cozy, clean, and relaxing. We really enjoyed our stay and would definitely come back!"
Canada
Sulaiman B.
$212 nightly
The price is $248
Aug 19 - Aug 20
Total with taxes and fees
Pet-Friendly Glamping Dome close to Peggy’s Cove!
Beach

18. Large Backyard Oasis near River and Trails

Large Backyard Oasis near River and Trails
Bridgewater
6.8 out of 10, (3 reviews)
"Perfect place to stay. We will be back for sure."
Canada
Geoff M.
$137 nightly
The price is $158
Aug 27 - Aug 28
Total with taxes and fees
Large Backyard Oasis near River and Trails
Interior

19. Executive 1-Bedroom King Bed Suite in Lunenburg (Suite 5)

Executive 1-Bedroom King Bed Suite in Lunenburg (Suite 5)
Lunenburg
8.4 out of 10, Very Good, (8 reviews)
"Great place tostay."
Canada
Bill
$269 nightly
The price is $307
Aug 13 - Aug 14
Total with taxes and fees
Executive 1-Bedroom King Bed Suite in Lunenburg (Suite 5)
1 bedroom, WiFi (free), bed sheets

20. 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, (28 reviews)
"Everything you need Welcome snacks were lovely Property well maintained Great amenities!"
Canada
Kelsea
$270 nightly
The price is $308
Aug 31 - Sep 1
Total with taxes and fees
Luxury lakefront dome with private beach, close to nature and town!
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

Miller House By the Bay

Miller House By the Bay

8/10 Good
"Well kept property Very convenient location Well appointed for the needs of travelers"
Colin 2-night trip
Posted less than an hour ago
Miller House By the Bay

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 $95 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 of 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 Lordly House Museum and Chester Playhouse. Chester Art Center and Tancook Island 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.