A calm lake with boats, a stone dock, and houses with a stone wall and trees in the background.

Chester Holiday Rentals

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Our top choices for Chester holiday 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
The price is HK$1,109
HK$1,442 total
includes taxes & fees
5 Oct - 6 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A small cabin with a deck, a door, and a window.

2. 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
The price is HK$1,109
HK$1,442 total
includes taxes & fees
30 Sept - 1 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A view of a waterfront property with a dock and a small building.

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

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore
9.2 out of 10, Wonderful, (27 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is HK$2,108
HK$3,265 total
includes taxes & fees
29 Sept - 30 Sept
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
A sunset view through a window with bare trees and a distant shoreline.

4. 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, (54 reviews)
"Sheets were stained and the house wasn’t up to my standards for cleanliness.It is cheap and a nice location and it was easy to communicate with the host."
Canada
Joanne
The price is HK$1,023
HK$1,344 total
includes taxes & fees
5 Oct - 6 Oct
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
A small, two-story cabin with a deck, large windows, and a fireplace.

5. 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.
The price is HK$1,109
HK$1,442 total
includes taxes & fees
8 Oct - 9 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A wooden door with a view of an outdoor deck and a chair.

6. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
8.8 out of 10, Excellent, (37 reviews)
"Check in and out was easy cute family that runs the place. Campground was very clean well-maintained fun areas for families for kids to play in the park fun pool washroom we're clean and maintained regularly. Definitely recommend for family fun."
Canada
David
The price is HK$660
HK$752 total
includes taxes & fees
28 Sept - 29 Sept
Oakhill Pines Campground
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.

7. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (80 reviews)
"The cabin was adorable, and the property was so clean. It was walking distance to everything in Mahone bay. Would definitely stay again!"
United States
Elizabeth
The price is HK$1,867
HK$2,318 total
includes taxes & fees
29 Sept - 30 Sept
Black Forest Cabins
A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.

8. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,330 reviews)
"Location is perfect"
Canada
Kelly
The price is HK$1,048
HK$1,195 total
includes taxes & fees
18 Oct - 19 Oct
Micro Boutique Living Wolfville
A porch with colorful Adirondack chairs and a wooden deck.

9. 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 HK$2,267
HK$2,836 total
includes taxes & fees
29 Sept - 30 Sept
Log Cabin #1 - Hubbards Beach
A dock with boats, a clear blue lake, and a forested island.

10. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.8 out of 10, Exceptional, (6 reviews)
"This property would be excellent for older couples and handicapped people. There's a ramp leading to the cottage and grab bars inside. Very peaceful and such a wonderful couple who owns it."
Canada
Betty
The price is HK$1,387
HK$2,074 total
includes taxes & fees
28 Sept - 29 Sept
Mermaid's Retreat - Caribou Lake Cottage!
A tented accommodation with a bed, two chairs, and a view of a lake.

11. 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, (36 reviews)
"The dome was well appointed and beautifully decorated. I would highly recommend it to anyone who wants a comfortable, relaxing getaway."
Canada
LISA
The price is HK$1,742
HK$2,353 total
includes taxes & fees
4 Oct - 5 Oct
Luxury lakefront dome with private beach, close to nature and town!
A residential area with a house, a swimming pool, and a marina with boats.

12. SUN, SAND, OCEAN, in Hubbards. What more do you need?

SUN, SAND, OCEAN, in Hubbards. What more do you need?
Hubbards
9.6 out of 10, Exceptional, (21 reviews)
"Lovely location. We enjoyed our stay and would go again."
United States
Angela C.
The price is HK$1,636
HK$2,919 total
includes taxes & fees
28 Sept - 29 Sept
SUN, SAND, OCEAN, in Hubbards. What more do you need?
A calm lake with boats docked at the pier, surrounded by trees.

13. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.6 out of 10, Exceptional, (10 reviews)
"Very clean, well-stocked, hospitable and comfortable space."
Canada
Rita
The price is HK$1,158
HK$1,813 total
includes taxes & fees
28 Sept - 29 Sept
Lake Mushamush Cottage!
A wooden deck with a view of a lake and trees.

14. 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 HK$2,872
HK$3,588 total
includes taxes & fees
18 Oct - 19 Oct
Beach Cottage - Oak Hollow - Hubbards Beach
A bright living room with a white sofa, a coffee table, and a potted plant.

15. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (116 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
The price is HK$1,109
HK$1,821 total
includes taxes & fees
17 Oct - 18 Oct
One bedroom fully equipped Mahone Bay luxury cottage
A kitchenette with a stainless steel refrigerator, a coffee maker on the counter, and a flat-screen TV mounted on the wall.

16. Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley
North Alton
9.0 out of 10, Wonderful, (4 reviews)
"So glad we chose to stay at Sakura Valley! Highly recommend! The host is lovely and accommodating, the suite was very clean, beds comfortable. Location is great! It feels secluded but is close to the highway. I would definitely stay again."
Canada
Nadia
The price is HK$624
HK$1,015 total
includes taxes & fees
28 Sept - 29 Sept
Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley

17. Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax

Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax
Boutiliers Point
9.8 out of 10, Exceptional, (20 reviews)
"It was cleaned and cozy stay with beautiful lake view"
Canada
Vikrant D.
The price is HK$2,002
HK$2,528 total
includes taxes & fees
15 Oct - 16 Oct
Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax
A small white cabin with green trim and a porch, surrounded by greenery.

18. 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 HK$1,391
HK$1,804 total
includes taxes & fees
29 Sept - 30 Sept
Orchard Cabin #4 - Hubbards Beach
A neatly made bed with a red quilt, two pillows, and two rolled towels.

19. 3 bedrooms 5 bed’s upper unit of duplex home

3 bedrooms 5 bed’s upper unit of duplex home
Kentville
9.0 out of 10, Wonderful, (14 reviews)
"Good location"
Canada
Holly
The price is HK$973
HK$1,913 total
includes taxes & fees
2 Oct - 3 Oct
3 bedrooms 5 bed’s upper unit of duplex home
A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

20. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (112 reviews)
"Comfortable cottage very close to town centre but also quiet and calm."
Canada
Richard
The price is HK$1,109
HK$1,821 total
includes taxes & fees
9 Oct - 10 Oct
Mahone Bay Hide-Away
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

Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

10/10 Excellent
"Staff were very helpful and accommodating. good recommendations for dinning."
Brian 1-night trip
Posted 10 hours ago
Days Inn & Conference Center by Wyndham Bridgewater