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Vacation Rentals in Chester

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Top Cities in Chester

Our top choices for Chester vacation rentals

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, (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
$183 nightly
The price is $208
Jan 4 - Jan 5, 2026
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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, (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
$151 nightly
The price is $172
Jan 18 - Jan 19, 2026
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Peaceful 2-Bedroom Coastal Cottage with Hot Tub

Peaceful 2-Bedroom Coastal Cottage with Hot Tub
Chester
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.
$273 nightly
The price is $312
Jan 1 - Jan 2, 2026
Total with taxes and fees
Peaceful 2-Bedroom Coastal Cottage with Hot Tub

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
Chester
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.
$231 nightly
The price is $263
Jan 19 - Jan 20, 2026
Total with taxes and fees
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
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.
$222 nightly
The price is $259
Dec 21 - Dec 22
Total with taxes and fees
Oceanfront Luxury Magical Views Sunset and Sunrise

Spacious Chester Home with Spectacular Ocean Views!

Spacious Chester Home with Spectacular Ocean Views!
2.0 star property
Chester
$439 nightly
The price is $501
Dec 24 - Dec 25
Total with taxes and fees
Spacious Chester Home with Spectacular Ocean Views!

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, (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.
$151 nightly
The price is $172
Jan 15 - Jan 16, 2026
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
9.0 out of 10, Wonderful, (16)
"Great place"
Canada
Thelma
$81 nightly
The price is $93
Dec 22 - Dec 23
Total with taxes and fees
Oakhill Pines Campground

Onyi’s cozy Himalaya

Onyi’s cozy Himalaya
Hammonds Plains
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
$100 nightly
The price is $117
Dec 24 - Dec 25
Total with taxes and fees
Onyi’s cozy Himalaya

Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
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

Wilson's Coastal Club - C6

Wilson's Coastal Club - C6
Boutiliers Point
10.0 out of 10, Exceptional, (9)
"Beautiful location! Great view of the bay.. "
Canada
Joan
$206 nightly
The price is $242
Jan 15 - Jan 16, 2026
Total with taxes and fees
Wilson's Coastal Club - C6

Sunny and Clean 1BR Suite Walk to LaHave River

Sunny and Clean 1BR Suite Walk to LaHave River
2.0 star property
Bridgewater
9.0 out of 10, Wonderful, (2)
"The host was fantastic and the apartment was clean and lovely."
Canada
JACQUELINE
$91 nightly
The price is $106
Dec 24 - Dec 25
Total with taxes and fees
Sunny and Clean 1BR Suite Walk to LaHave River

Private Lakefront Escape | Swim, Sip Wine & Stargaze | 25 Mins to Halifax

Private Lakefront Escape | Swim, Sip Wine & Stargaze | 25 Mins to Halifax
Brookside
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.
$221 nightly
The price is $258
Jan 19 - Jan 20, 2026
Total with taxes and fees
Private Lakefront Escape | Swim, Sip Wine & Stargaze | 25 Mins to Halifax

Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!

Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!
Bedford
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
$129 nightly
The price is $150
Dec 24 - Dec 25
Total with taxes and fees
Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!

Lakeview Breaktrail Stays is a fully furnished 1-bedroom & separate living room

Lakeview Breaktrail Stays is a fully furnished 1-bedroom & separate living room
2.0 star property
Bedford
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.
$98 nightly
The price is $115
Dec 24 - Dec 25
Total with taxes and fees
Lakeview Breaktrail Stays is a fully furnished 1-bedroom & separate living room

Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1097)
"Loved staying here💕"
Canada
Deborah
Micro Boutique Living Wolfville

Suite 201 - 470 Main

Suite 201 - 470 Main
Wolfville
$182 nightly
The price is $201
Jan 5 - Jan 6, 2026
Total with taxes and fees
Suite 201 - 470 Main

Private Balcony View Riverside Walk Prime Downtown

Private Balcony View Riverside Walk Prime Downtown
2.0 star property
Bridgewater
$96 nightly
The price is $111
Dec 25 - Dec 26
Total with taxes and fees
Private Balcony View Riverside Walk Prime Downtown

Charming private basement suite with kingsize bed in brilliant Halifax

Charming private basement suite with kingsize bed in brilliant Halifax
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.
$142 nightly
The price is $166
Jan 18 - Jan 19, 2026
Total with taxes and fees
Charming private basement suite with kingsize bed in brilliant Halifax

Armdale Retreat + Free Photoshoot!

Armdale Retreat + Free Photoshoot!
2.0 star property
Halifax
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.
$104 nightly
The price is $122
Dec 30 - Dec 31
Total with taxes and fees
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.
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Top Chester Hotel Reviews

Find out more about Chester

Discover your perfect Chester vacation rental with Expedia

How many vacation rentals are available in Chester?


Expedia has plenty of vacation rentals to choose from in and around  Chester, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Chester?


The selection of Chester vacation rentals we have selected for you start as low as $117 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Chester?


Vacation rentals in Chester come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Chester vacation rentals to suit everyone. 


Why should I choose a vacation rental in Chester?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Chester?


Find vacation rentals in Chester by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Chester.  


What amenities are available in a vacation rental in Chester?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Chester vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Chester?   


Everytime is a great time to head to Chester! Staying in a Chester vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Chester. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Chester vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Chester, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Chester vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.