Chester Vacation Rentals

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Top Cities in Chester

Top Vacation Rentals in in Chester

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, (12)
"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

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."
The price is CA $180
CA $236 total
includes taxes & fees
Sep 22 - Sep 23
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

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.

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

Cozy Oceanfront Escape with Hot Tub

10.0 out of 10, Exceptional, (18)
"This spot was beyond my wife and i expectations. Would definitely recommend anyone to experience the beautiful views great accommodations."
Cozy Oceanfront Escape with Hot Tub

Spectacular Oceanfront Living in Authentic Fishing Village

10.0 out of 10, Exceptional, (108)
"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

Micro Boutique Living Wolfville

3.5 star property
9.0 out of 10, Wonderful, (1077)
"Loved staying here💕"
Micro Boutique Living Wolfville

Oakhill Pines Campground

3.0 star property
9.2 out of 10, Wonderful, (9)
"Great place"
The price is CA $119
CA $136 total
includes taxes & fees
Aug 31 - Sep 1
Oakhill Pines Campground

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 "
The price is CA $311
CA $389 total
includes taxes & fees
Sep 7 - Sep 8
Black Forest Cabins

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. "
The price is CA $108
CA $345 total
includes taxes & fees
Sep 1 - Sep 2
Cute n Lovely

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

9.0 out of 10, Wonderful, (2)
"Overall very comfortable and clean. Comfortable inside the tent and patio nice and big. Small shared outdoor bathroom and no outdoor sink to do dishes. Enjoyed our stay."
The price is CA $120
CA $201 total
includes taxes & fees
Sep 1 - Sep 2
Juniper Bell Tent near Peggy's Cove

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (105)
"Property was wonderful, love Lunenburg and area would definitely return!!!"
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

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

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! "
The price is CA $200
CA $369 total
includes taxes & fees
Sep 1 - Sep 2
Artistic Getaway Near Halifax | King Bed, Spacious Deck & Fire Pit

One bedroom fully equipped Mahone Bay luxury cottage

10.0 out of 10, Exceptional, (99)
"I really appreciated having the washer and dryer in the unit. It was walkable to all areas in Mahone Bay."
One bedroom fully equipped Mahone Bay luxury cottage

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."
The price is CA $650
CA $1,321 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful Retreat on Schmidt Lake
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

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Chester vacation rentals we have selected for you start as low as CA $108 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.