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

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, (66 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
The price is AED 768
AED 966 total
includes taxes & fees
17 Aug - 18 Aug
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.
The price is AED 1,436
AED 2,228 total
includes taxes & fees
6 Sep - 7 Sep
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
The price is AED 527
AED 688 total
includes taxes & fees
30 Aug - 31 Aug
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
The price is AED 307
AED 350 total
includes taxes & fees
8 Sep - 9 Sep
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
The price is AED 617
AED 805 total
includes taxes & fees
16 Aug - 17 Aug
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
The price is AED 883
AED 1,247 total
includes taxes & fees
31 Aug - 1 Sep
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.
The price is AED 593
AED 973 total
includes taxes & fees
16 Aug - 17 Aug
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.
The price is AED 856
AED 1,579 total
includes taxes & fees
6 Sep - 7 Sep
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
The price is AED 593
AED 973 total
includes taxes & fees
30 Aug - 31 Aug
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.
The price is AED 988
AED 1,318 total
includes taxes & fees
8 Sep - 9 Sep
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, (2 reviews)
"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.
The price is AED 1,318
AED 1,755 total
includes taxes & fees
8 Sep - 9 Sep
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.
The price is AED 719
AED 959 total
includes taxes & fees
18 Aug - 19 Aug
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.
The price is AED 461
AED 796 total
includes taxes & fees
13 Aug - 14 Aug
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
The price is AED 1,199
AED 1,598 total
includes taxes & fees
8 Sep - 9 Sep
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.
The price is AED 1,038
AED 1,382 total
includes taxes & fees
8 Sep - 9 Sep
Log Cabin #2 - Hubbards Beach
Terrace/patio

16. Beach Cottage - Chestnut - Hubbards Beach

Beach Cottage - Chestnut - Hubbards Beach
Hubbards
The price is AED 1,314
AED 1,751 total
includes taxes & fees
8 Sep - 9 Sep
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.
The price is AED 1,199
AED 1,598 total
includes taxes & fees
8 Sep - 9 Sep
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.
The price is AED 1,049
AED 1,871 total
includes taxes & fees
3 Sep - 4 Sep
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.
The price is AED 771
AED 1,278 total
includes taxes & fees
18 Aug - 19 Aug
Oceanfront Kayaking retreat close to Lunenburg
Interior

20. Beach Cottage - Whispering Firs - Hubbards Beach

Beach Cottage - Whispering Firs - Hubbards Beach
Hubbards
The price is AED 1,502
AED 2,001 total
includes taxes & fees
23 Aug - 24 Aug
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

Clifty Cove Motel

Clifty Cove Motel

10/10 Excellent
"Great location-close to Peggy's Cove. Rooms were clean with a great view."
tracey 1-night trip
Posted 10 hours ago
Clifty Cove Motel

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.