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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
$182 nightly
The price is $207
Dec 22 - Dec 23
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
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
Dec 22 - Dec 23
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.
$279 nightly
The price is $318
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
Dec 22 - Dec 23
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 22 - Dec 23
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
$436 nightly
The price is $497
Dec 22 - Dec 23
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
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
Dec 22 - Dec 23
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

The Eagle's Landing on Minamkeak Lake

The Eagle's Landing on Minamkeak Lake
Italy Cross
9.8 out of 10, Exceptional, (88)
"Absolutely stunning location. "
Canada
Benjaminr
$171 nightly
The price is $195
Dec 22 - Dec 23
Total with taxes and fees
The Eagle's Landing on Minamkeak Lake

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.
$211 nightly
The price is $247
Jan 4 - Jan 5, 2026
Total with taxes and fees
Private Lakefront Escape | Swim, Sip Wine & Stargaze | 25 Mins to Halifax

Shackup A-frame— Private Hot Tub & Beach Access

Shackup A-frame— Private Hot Tub & Beach Access
La Have
10.0 out of 10, Exceptional, (3)
"We can't say enough good things about the house! The design is impeccable and the property is peaceful and lovely. Our only regret was not staying longer! We look forward to going back again one day and will be sure to recommend it to anyone we know. "
Canada
Nicola S.
$238 nightly
The price is $271
Jan 6 - Jan 7, 2026
Total with taxes and fees
Shackup A-frame— Private Hot Tub & Beach Access

Red Roof Bed & Breakfast

Red Roof Bed & Breakfast
Lunenburg
9.6 out of 10, Exceptional, (9)
"A lovely little cottage, with the added bonus of a gift shop filled with curious trinkets! Would definitely stay here again if I’m ever back in Lunenberg."
Canada
Raeleen
$173 nightly
The price is $197
Dec 22 - Dec 23
Total with taxes and fees
Red Roof Bed & Breakfast

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 22 - Dec 23
Total with taxes and fees
Onyi’s cozy Himalaya

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

Suite 301 - 470 Main

Suite 301 - 470 Main
Wolfville
10.0 out of 10, Exceptional, (1)
"This place exceeded expectations. Our only regret is that we didn't stay longer."
Canada
victoria
$178 nightly
The price is $197
Dec 22 - Dec 23
Total with taxes and fees
Suite 301 - 470 Main

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 22 - Dec 23
Total with taxes and fees
Cozy Private Walk-in Basement | Bed, Living Room & Kitchenette!

Wilson's Coastal Club - C3

Wilson's Coastal Club - C3
Boutiliers Point
9.8 out of 10, Exceptional, (10)
"Very nice cottage, steps from the beach"
United States
Christine
$173 nightly
The price is $203
Jan 13 - Jan 14, 2026
Total with taxes and fees
Wilson's Coastal Club - C3

Hot Choco Bar Backyard Access Private Entry

Hot Choco Bar Backyard Access Private Entry
2.0 star property
Bridgewater
10.0 out of 10, Exceptional, (1)
"Perfect place to stay. We will be back for sure."
Canada
Geoff M.
$107 nightly
The price is $124
Dec 22 - Dec 23
Total with taxes and fees
Hot Choco Bar Backyard Access Private Entry

Shackup Cabin— Wood Fired Hot Tub & Near the beach

Shackup Cabin— Wood Fired Hot Tub & Near the beach
West Dublin
10.0 out of 10, Exceptional, (4)
"Fantastic little hideaway. Very comfortable and private"
Canada
Adam
$191 nightly
The price is $217
Jan 4 - Jan 5, 2026
Total with taxes and fees
Shackup Cabin— Wood Fired Hot Tub & Near the beach

Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
Bridgewater
9.4 out of 10, Exceptional, (3)
"As described and in a great location!"
United States
Erin E.
$215 nightly
The price is $252
Dec 26 - Dec 27
Total with taxes and fees
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
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.
Save an average of 15% on thousands of hotels when you're signed in

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.