Vacation Rentals in Chester

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Top Cities in Chester

Top Vacation Rentals in Chester

Our top choices for Chester vacation rentals

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

8.0 out of 10, Very Good, (23)
"The property is as we have expected. one of the additional benefits are the board games and card games provided. Kids just love them."
$150 nightly
The price is $171
Sep 18 - Sep 19
Total with taxes and fees
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

9.6 out of 10, Exceptional, (31)
"We loved the privacy and view of ocean. Loved watching the tide go in and out, that was so amazing. Missed having a sandy beach to walk on. Otherwise , fantastic. Golf course restaurant was amazing as well. "
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Moonlight Cottage

9.8 out of 10, Exceptional, (13)
"Loved getting to come stay at the house that was the Grey Gull on Haven the TV show! The host was great with communicating and our stay was awesome."
Moonlight Cottage

Ocean front cottage in the heart of Hubbards.

9.8 out of 10, Exceptional, (50)
"Excellent week with the kids. Hosts were great. "
Ocean front cottage in the heart of Hubbards.

Oceanfront Luxury Magical Views Sunset and Sunrise

9.6 out of 10, Exceptional, (17)
"Short stay, unfortunately, but I’ll definitely be back. "
Oceanfront Luxury Magical Views Sunset and Sunrise

Amazing ocean view/ private road/close to bayswater beach.

8.6 out of 10, Excellent, (44)
"We enjoyed the location and house. Made a great place to stay on the water near Peggy’s Cove and Lunenburg."
Amazing ocean view/ private road/close to bayswater beach.

Spectacular Oceanfront Living in Authentic Fishing Village

10.0 out of 10, Exceptional, (109)
"A family member was getting married in Hubbards this weekend and we were her decorating crew so needed somewhere to stay. The house was perfect it slept all 13 of us (10 adults, 3 little kids), it was clean, well maintained and had absolutely stunning views. Kelly was absolutely wonderful to deal with, we will definitely be back! "
Spectacular Oceanfront Living in Authentic Fishing Village

Stunning Ocean Front cottage, minutes from the beach

10.0 out of 10, Exceptional, (27)
"This property was clean, well stocked with items we would need, had a fabulous view the water. The host was very friendly and quick to respond. We had an amazing stay and would highly recommend this property if you are looking for some relaxation yet still driveable to tourist spots (1 hour +/-)."
Stunning Ocean Front cottage, minutes from the beach

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

10.0 out of 10, Exceptional, (91)
"We loved the view, everything we needed was available and more. All our requests and concerns were answered immediately. All 🛌 were clean and comfortable."
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Micro Boutique Living Wolfville

3.5 star property
9.0 out of 10, Wonderful, (1083)
"Loved staying here💕"
Micro Boutique Living Wolfville

Oakhill Pines Campground

3.0 star property
9.2 out of 10, Wonderful, (9)
"Great place"
$86 nightly
The price is $98
Sep 7 - Sep 8
Total with taxes and fees
Oakhill Pines Campground

Cute n Lovely

6.8 out of 10, (3)
"The property was very clean and had everything we need and the location was great. Only issue with it being a lower apartment we found at times and sometimes early in morning children were loud. "
$212 nightly
The price is $248
Sep 7 - Sep 8
Total with taxes and fees
Cute n Lovely

Cozy stay overlooking the bedford basin

9.6 out of 10, Exceptional, (4)
"Zoe was a kind and generous host. Communication was great! The accommodation was comfortable and as described. Great view of Bedford basin, a little noisy if sitting outside but quiet inside.We would recommend this rental."
$228 nightly
The price is $266
Sep 10 - Sep 11
Total with taxes and fees
Cozy stay overlooking the bedford basin

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (9)
"Great spot for a special night out … beds were super comfortable "
$230 nightly
The price is $262
Oct 7 - Oct 8
Total with taxes and fees
Black Forest Cabins

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (105)
"Wonderful. Great cottage."
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

9.8 out of 10, Exceptional, (122)
"We loved Whaleback Cottage! It was very comfortable and clean with incredible views! Tom and Donna were great hosts! We would definitely stay there again."
Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

Juniper Bell Tent near Peggy's Cove

8.8 out of 10, Excellent, (3)
"Good for a nights stay and close to Peggy’s cove. Comfy and enough space"
$125 nightly
The price is $146
Sep 7 - Sep 8
Total with taxes and fees
Juniper Bell Tent near Peggy's Cove

The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

9.8 out of 10, Exceptional, (220)
"We had an absolutely wonderful time on the Land Yacht, the kids used the pool everyday and we all thoroughly enjoyed the perfect weather from the solarium :) The Land Yacht in an incredible spot and we will definitely be back again."
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

Peaceful Retreat on Schmidt Lake

10.0 out of 10, Exceptional, (2)
"We had an amazing time at this property, its the perfect property for a summer get away. The hosts responded promptly and check in was seamless."
$826 nightly
The price is $955
Sep 7 - Sep 8
Total with taxes and fees
Peaceful Retreat on Schmidt Lake

Artistic Getaway Near Halifax | King Bed, Spacious Deck & Fire Pit

9.4 out of 10, Exceptional, (22)
"Property was clean, and owner was helpful and quickly responded to any questions. Would love to stay again and definitely would recommend! "
$226 nightly
The price is $265
Sep 7 - Sep 8
Total with taxes and fees
Artistic Getaway Near Halifax | King Bed, Spacious Deck & Fire Pit
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

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 $98 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.