Photo by Rachel Kent

Vacation Rentals in Chester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Our top choices for Chester vacation rentals

Outdoor spa tub
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Chalet in Windsor Road

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
10.0 out of 10, Exceptional, (7)
"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 ￥20,330
￥32,318 total
includes taxes & fees
Dec 22 - Dec 23
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Interior
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Chalet in Chester Basin

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
9.8 out of 10, Exceptional, (14)
"There’s so much about Dordéan Suites to like: a contemporary, fun alternative to large, impersonal corporate roadside hotel. Loved our place, loved our stay! "
United States
Karil
The price is ￥20,330
￥26,781 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Terrace/patio
Peaceful 2-Bedroom Coastal Cottage with Hot Tub

Apartment in Chester

Peaceful 2-Bedroom Coastal Cottage with Hot Tub
10.0 out of 10, Exceptional, (8)
"Stayed for 3 nights and enjoyed everything about this cottage - it's exactly as advertised. Great location - very private, quiet and high end. Will be back!"
Canada
Chris M.
The price is ￥29,518
￥50,260 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Peaceful 2-Bedroom Coastal Cottage with Hot Tub
Living area
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Cottage in Chester

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
9.0 out of 10, Wonderful, (2)
"It was the perfect get away for myself after a rough week at work! Highly recommend. "
Canada
Michelle L.
The price is ￥31,511
￥41,073 total
includes taxes & fees
Dec 21 - Dec 22
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
Marina
Oceanfront Luxury Magical Views Sunset and Sunrise

Vacation Home in Western Shore

Oceanfront Luxury Magical Views Sunset and Sunrise
9.6 out of 10, Exceptional, (20)
"Excellent unit and very clean.The view was awesome.Highly recommended for a wonderful place to stay."
Canada
John S.
The price is ￥24,847
￥42,021 total
includes taxes & fees
Dec 21 - Dec 22
Oceanfront Luxury Magical Views Sunset and Sunrise
Outdoor dining
Spacious Chester Home with Spectacular Ocean Views!

Vacation Home in Chester

Spacious Chester Home with Spectacular Ocean Views!
2.0 star property
The price is ￥31,624
￥77,510 total
includes taxes & fees
Dec 21 - Dec 22
Spacious Chester Home with Spectacular Ocean Views!
Exterior
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Chalet in Chester Basin

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
10.0 out of 10, Exceptional, (16)
"What an amazing and magical place. Accommodations are excellent. The small houses have everything you need and then some. Highly recommend this place. "
Canada
Paul G.
The price is ￥20,330
￥26,781 total
includes taxes & fees
Dec 22 - Dec 23
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Cabin, Multiple Beds, Shared Bathroom | Desk, free WiFi
Oakhill Pines Campground

Cabin in Oak Hill

Oakhill Pines Campground
3.0 star property
9.0 out of 10, Wonderful, (16)
"Great place"
Canada
Thelma
The price is ￥12,649
￥14,420 total
includes taxes & fees
Dec 21 - Dec 22
Oakhill Pines Campground
1 bedroom, WiFi, bed sheets
Onyi’s cozy Himalaya

Vacation Home in Hammonds Plains

Onyi’s cozy Himalaya
8.4 out of 10, Very Good, (5)
"The place was very clean, it had everything we needed. The area is nice and plenty of walking trails and lakes. The host was nice and accommodating. The building could use more spund proofing as we could hear toddlers and stomping, but other than that everything was perfect. I can't wait to come back again."
United States
Salima
The price is ￥10,729
￥18,192 total
includes taxes & fees
Dec 21 - Dec 22
Onyi’s cozy Himalaya
Meeting facility
Black Forest Cabins

Cabin in Mahone Bay

Black Forest Cabins
3.0 star property
10.0 out of 10, Exceptional, (20)
"Bed was very comfortable,and clean and spacious. Everything I needed was there and close to trails and the downtown."
Canada
Mary
Black Forest Cabins
Sauna
Wilson's Coastal Club - C6

Cottage in Boutiliers Point

Wilson's Coastal Club - C6
10.0 out of 10, Exceptional, (9)
"Beautiful location! Great view of the bay.. "
Canada
Joan
The price is ￥28,123
￥37,658 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wilson's Coastal Club - C6
Fridge, microwave, oven, stovetop
Sunny and Clean 1BR Suite Walk to LaHave River

Apartment in Bridgewater

Sunny and Clean 1BR Suite Walk to LaHave River
2.0 star property
9.0 out of 10, Wonderful, (2)
"The host was fantastic and the apartment was clean and lovely."
Canada
JACQUELINE
The price is ￥8,809
￥16,487 total
includes taxes & fees
Dec 21 - Dec 22
Sunny and Clean 1BR Suite Walk to LaHave River
Fridge, microwave, oven, stovetop
Private Lakefront Escape | Swim, Sip Wine & Stargaze | 25 Mins to Halifax

Vacation Home in Brookside

Private Lakefront Escape | Swim, Sip Wine & Stargaze | 25 Mins to Halifax
8.8 out of 10, Excellent, (27)
"Cozy cottage right on beautiful lake. The place was clean and had all the necessities for a comfortable stay. Excellent communication with the host. "
United States
Mary Ellen B.
The price is ￥14,417
￥40,387 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Lakefront Escape | Swim, Sip Wine & Stargaze | 25 Mins to Halifax
Property grounds
Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!

Vacation Home in Bedford

Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!
9.6 out of 10, Exceptional, (7)
"Very clean,nice walking trail close by,easy accessible,hostess was very nice and helpfull,highly recommend ."
Canada
Linda
The price is ￥10,673
￥23,432 total
includes taxes & fees
Dec 21 - Dec 22
Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!
Fridge, microwave, oven, stovetop
Lakeview Breaktrail Stays is a fully furnished 1-bedroom & separate living room

Vacation Home in Bedford

Lakeview Breaktrail Stays is a fully furnished 1-bedroom & separate living room
2.0 star property
10.0 out of 10, Exceptional, (1)
"Jennifer is an amazing host. Her place has everything we needed. Very responsive and was able to accommodate an unexpected extra night. "
Canada
Joana B.
The price is ￥9,961
￥18,618 total
includes taxes & fees
Dec 28 - Dec 29
Lakeview Breaktrail Stays is a fully furnished 1-bedroom & separate living room
Studio Suite, Kitchenette, Ocean View | Water view
Micro Boutique Living Wolfville

Apartment in Wolfville

Micro Boutique Living Wolfville
3.5 star property
9.0 out of 10, Wonderful, (1097)
"Loved staying here💕"
Canada
Deborah
Micro Boutique Living Wolfville
Interior
Suite 201 - 470 Main

Apartment in Wolfville

Suite 201 - 470 Main
The price is ￥18,443
￥31,921 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Suite 201 - 470 Main
Fridge, microwave, oven, stovetop
Private Balcony View Riverside Walk Prime Downtown

Vacation Home in Bridgewater

Private Balcony View Riverside Walk Prime Downtown
2.0 star property
The price is ￥7,906
￥17,361 total
includes taxes & fees
Dec 23 - Dec 24
Private Balcony View Riverside Walk Prime Downtown
Smart TV, fireplace
Charming private basement suite with kingsize bed in brilliant Halifax

Apartment in Halifax

Charming private basement suite with kingsize bed in brilliant Halifax
9.0 out of 10, Wonderful, (10)
"Splendid… Spotless… Supplied “Charming private basement apartment with kingsize bed in brilliant Halifax” is all it claims and more. The pictures are accurate. It was spotlessly clean and well supplied for our three-night stay in Halifax. A perfect and restful spot while we explored the Halifax Harbor and Peggy’s Cove and the south shore. Highly recommended. Richard."
Canada
Richard R.
The price is ￥13,101
￥26,813 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Charming private basement suite with kingsize bed in brilliant Halifax
Smart TV, books
Armdale Retreat + Free Photoshoot!

Apartment in Halifax

Armdale Retreat + Free Photoshoot!
2.0 star property
10.0 out of 10, Exceptional, (1)
"I had a wonderful stay at Armadale Retreat. The host was incredibly communicative and welcoming. The location was perfect. And the accomodation was comfortable. Super clean, a warm atmosphere, all the amenities needed, and very quiet and peaceful - especially appreciated being on a work trip. I would stay again and recommend highly.Thank you again Antonio "
Canada
Sarah T.
The price is ￥10,775
￥18,909 total
includes taxes & fees
Dec 30 - Dec 31
Armdale Retreat + Free Photoshoot!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Holiday Inn Express & Suites Halifax - Bedford by IHG

Holiday Inn Express & Suites Halifax - Bedford by IHG

10/10 Excellent
"The front desk person was so outgoing and made me laugh. He's very good at his job and amazing with the public"
Courtney 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Halifax - Bedford by IHG

Find out more about Chester

Vacation Apartments in Chester

Search for Vacation rentals in Chester on Expedia! You can easily find your home rentals, villas, Vacation apartments in Chester using one of the methods below:

  • View our selection of featured Vacation rentals in Chester
  • Use the map to find apartments and other Vacation homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!