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 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (65 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
$230 nightly
The price is $262
Sep 2 - Sep 3
Total with taxes and fees
Black Forest Cabins
Property grounds

2. 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.
$529 nightly
The price is $617
Sep 6 - Sep 7
Total with taxes and fees
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Outdoor spa tub

3. 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
$163 nightly
The price is $186
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)

4. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
9.0 out of 10, Wonderful, (22 reviews)
"Staff was super welcoming and cabin was all set for us! "
Canada
Andrea
$81 nightly
The price is $92
Aug 18 - Aug 19
Total with taxes and fees
Oakhill Pines Campground
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, (42 reviews)
"Have use of all the facilities (laundry) was extremely helpful when travelling with a toddler."
Canada
Lisa
$191 nightly
The price is $218
Aug 16 - Aug 17
Total with taxes and fees
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
1 bedroom, WiFi (free), bed sheets

6. 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, (27 reviews)
"Everything you need Welcome snacks were lovely Property well maintained Great amenities!"
Canada
Kelsea
$296 nightly
The price is $338
Aug 31 - Sep 1
Total with taxes and fees
Luxury lakefront dome with private beach, close to nature and town!
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.
$231 nightly
The price is $264
Aug 16 - Aug 17
Total with taxes and fees
One bedroom fully equipped Mahone Bay luxury cottage
Terrace/patio

8. SUN, SAND, OCEAN in Hubbards Nova Scotia

SUN, SAND, OCEAN in Hubbards Nova Scotia
Hubbards
9.4 out of 10, Exceptional, (8 reviews)
"Cottage location was ideal for seeing sites in the area. We loved sitting on the dock, watching sunsets and relaxing. We would definitely recommend this rental."
Canada
Gloria L.
$365 nightly
The price is $428
Sep 6 - Sep 7
Total with taxes and fees
SUN, SAND, OCEAN in Hubbards Nova Scotia
TV

9. 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
$231 nightly
The price is $264
Aug 27 - Aug 28
Total with taxes and fees
One bedroom fully equipped Mahone Bay luxury cottage
Terrace/patio

10. Log Cabin #1 - Hubbards Beach

Log Cabin #1 - Hubbards Beach
Hubbards
9.6 out of 10, Exceptional, (5 reviews)
"A wonderful cottage with character!! Comfy beds, nice pillows! Very rustic, very peaceful"
Canada
Lisa R.
$408 nightly
The price is $475
Aug 12 - Aug 13
Total with taxes and fees
Log Cabin #1 - Hubbards Beach
Property grounds

11. Beach Cottage - Oak Hollow - Hubbards Beach

Beach Cottage - Oak Hollow - Hubbards Beach
Hubbards
10.0 out of 10, Exceptional, (1 review)
"Jared (the owner) made our stay at Hubbards beach one we wont soon forget. The staff accommodated our every need, going above and beyond to secure us provisions when all the shops were closed for canada day. The cottage (oak hollow) was spacious, comfortably sleeping 5 adults, with a rustic and comfortable decor. The fireplace in the cottage saw a lot of use and was fully stocked with wood at no cost. Steps from the gorgeous hubbards beach, this spot had no shortage of activities to keep us...
Canada
CHRISTIAN P.
$570 nightly
The price is $665
Aug 12 - Aug 13
Total with taxes and fees
Beach Cottage - Oak Hollow - Hubbards Beach
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
Interior

13. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (106 reviews)
"Close to restaurants, sights, many walking distance. Clean, bright, lodgings. Welcoming and helpful hosts. Would recommend to anyone "
Canada
Nancy R.
$189 nightly
The price is $216
Aug 13 - Aug 14
Total with taxes and fees
Mahone Bay Hide-Away
Terrace/patio

14. Beach Cottage - Spruce Grove - Hubbards Beach

Beach Cottage - Spruce Grove - Hubbards Beach
Hubbards
10.0 out of 10, Exceptional, (3 reviews)
"Positively lovely ❤️. Relaxing with beautiful views!"
Canada
Angela
$465 nightly
The price is $542
Aug 9 - Aug 10
Total with taxes and fees
Beach Cottage - Spruce Grove - Hubbards Beach
Terrace/patio

15. Log Cabin #2 - Hubbards Beach

Log Cabin #2 - Hubbards Beach
Hubbards
10.0 out of 10, Exceptional, (1 review)
"As advertised and 2 minutes from the shore club."
Canada
Jody K.
$428 nightly
The price is $499
Aug 23 - Aug 24
Total with taxes and fees
Log Cabin #2 - Hubbards Beach
Terrace/patio

16. Beach Cottage - Chestnut - Hubbards Beach

Beach Cottage - Chestnut - Hubbards Beach
Hubbards
$556 nightly
The price is $649
Aug 30 - Aug 31
Total with taxes and fees
Beach Cottage - Chestnut - Hubbards Beach
Property grounds

17. Beach Cottage - Yellow Birches - Hubbards Beach

Beach Cottage - Yellow Birches - Hubbards Beach
Hubbards
8.0 out of 10, Very Good, (1 review)
"Hubbard’s is such a great little area and the beach is beautiful. I come here every summer and have stayed in most of these cottages. Cottage had everything you need, lots of towels, extra blankets, water cooler, etc. Staff is extremely friendly at check in, garbage pickup, and all the restaurants. Our cottage had a beautiful view of the pond and ocean, a good sized deck with barbecue, a nice lawn area for activities, and space for parking. It had a very rustic cottage-like vibe which is what I...
Canada
Alea L.
$448 nightly
The price is $522
Aug 16 - Aug 17
Total with taxes and fees
Beach Cottage - Yellow Birches - Hubbards Beach
Smart TV, fireplace, video games, DVD player

18. The Salty Cribb II- Private oceanfront vacation home just minutes from Lunenburg

The Salty Cribb II- Private oceanfront vacation home just minutes from Lunenburg
Rose Bay
9.8 out of 10, Exceptional, (45 reviews)
"Views, location and quality of accommodations were just right."
Canada
Thomas P.
$445 nightly
The price is $507
Sep 3 - Sep 4
Total with taxes and fees
The Salty Cribb II- Private oceanfront vacation home just minutes from Lunenburg
Terrace/patio

19. 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
Interior

20. Beach Cottage - Whispering Firs - Hubbards Beach

Beach Cottage - Whispering Firs - Hubbards Beach
Hubbards
$465 nightly
The price is $542
Aug 23 - Aug 24
Total with taxes and fees
Beach Cottage - Whispering Firs - Hubbards Beach
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
"It was sparkling clean; had everything we needed; owner was friendly and helpful"
Muriel 1-night trip
Posted 1 hour 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 $173 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 Chester Playhouse and Lordly House Museum. 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.