Discover a selection of 169 vacation rentals in Chester, CA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $112 per night, and houses and cottages are popular options for a stay in Chester. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chester
Destination guide

Find the perfect vacation rental for your Chester getaway

Learn about the unique charm of Chester with a stay in a private vacation home. This city has something for everyone. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Things to do

Activities and attractions in Chester

Are you hoping to find attractions to see during your stay? Venture out of your vacation home and experience everything that makes Chester a fun spot to vacation. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Chester Golf Club (6.9 mi / 11.1 km)
  • Shore Club Dance Hall (11.3 mi / 18.2 km)
  • The Dog Shop Bathhouse & Boutique (13.1 mi / 21 km)
  • Bluenose Golf Club (17.8 mi / 28.7 km)
  • Ski Martock (22 mi / 35.3 km)
  • Hatfield Farm (26.4 mi / 42.5 km)
Natural features

Exploring the natural features in Chester

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Chester is a great place to get out in nature. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Graves Island Provincial Park (6 mi / 9.7 km)
  • Oak Island (7.8 mi / 12.6 km)
  • Hubbards Beach (11.6 mi / 18.6 km)
  • Queensland Beach Provincial Park (12.9 mi / 20.7 km)
  • Saint Margarets Bay Look Off Park (16.8 mi / 27.1 km)
  • Saint Margarets Bay (18.2 mi / 29.3 km)

What are the top vacation rentals in Chester?

Whether you're planning your next epic adventure with pals or a romantic getaway with your darling, one of these top vacation rentals in Chester is sure to attract you:

  • "4 Bed - - Persons Vacation Rental With Cottage": If you're on the hunt for a comfy living space in Middle River, this escape won't disappoint. It comes with 4 bedrooms and amenities like a kitchen and off-street parking options.
  • "A Sailors Paradise - Stevens Cove Guest Quarters": Located in Chester, this sought-after getaway has 1 bedroom and lots of handy amenities. Cookware, dishware and utensils and a fridge are just a couple you'll find here.

For even more great options, use the search bar at the top of the page to find the perfect Chester vacation rental for you.

What are the best tiny house vacation rentals in Chester?

For a completely different experience, book a tiny house rental in Chester. Be warned though — after you've experienced what it's like in a tiny house, the urge to move into one of thes miniature digs will be tough to resist!

  • Take a few days off to recharge at "Tiny House Living In Lunenburg Town". Located in Lunenburg County, a fridge and cookware, dishware and utensils are a couple of amenities on offer here.
  • "Tiny Delight Tiny House With Own Beach And Waterfall 7km To Inverness Cape Breton" in Canada - New England is another superb option. Nearby hunting activities and an electric kettle will help make your time here extra comfortable.

What are the top-rated vacation rentals for weekend getaways in Chester?

Whether you're organizing a family get-together, some romantic "us" time or a couple of nights away alone, we have weekend getaways in Chester to suit your style. Throw some clothes into an overnight bag and stay at one of these popular properties:

  • "Serenity Cottage Borders The Beautiful Coveside Stable In Chester" - Located in Chester, there's oodles of awesome stuff to see and do near this rental. Handy extras like air conditioning and free toiletries are the cherry on top!
  • "Superb Oceanfront With Optional Boathouse" - With a living room and free WiFi, not to mention its convenient location in Canada - New England, you'll wish you had more than a weekend at this rental property.

Can I find studio apartments for rent in Chester?

Ditch the lifeless hotel room and opt for one of our studio apartments in Chester. Here's where you can hole up in your own digs and experience your next destination like a local:

  • Get comfy at "A Sailors Paradise - Stevens Cove Guest Quarters", situated in Chester. There are loads of amenities at your fingertips here, including a nearby beach and a hair dryer.
  • Alternatively, use "Delightful Self Contained Cottage In The Charming Village Of Chester By The Sea" as your base to get out and explore the area. This appealing retreat is in Chester and offers coffee and tea making facilities and a kitchen.

Can I find short term rentals in Chester?

Chester has short-term rentals that come in all shapes, sizes and budgets. Take some time out in a cheap cabin, a luxurious condo or whatever else floats your boat. Here are a couple of options to consider:

  • "Serenity Cottage Borders The Beautiful Coveside Stable In Chester" in Chester is an ideal place for a short-term stay. It's only a short distance from the town center, so you can easily get out to see all the best sights without having to travel too far.
  • Another welcoming option is "Superb Oceanfront With Optional Boathouse" in Canada - New England. Whether you're breaking up a road trip or enjoying a couple of days away, this comfortable vacation rental will make you feel right at home.

What are the best large group vacation rentals in Chester?

If your idea of a dream trip away is to bring along all your besties, you'll be needing a whole lot of space. Luckily, there are plenty of vacation rentals in Chester that are suitable for large groups, starting with these sprawling escapes:

  • "The White Cape On The Cove - A Year Round Oceanside Retreat": With 6 bedrooms, everyone can be a part of the fun at this sought-after retreat in Chandon. A fireplace and a kitchen are among the many amenities available here.
  • "Spectacular Oceanfront Living In Authentic Fishing Village": You'll get your squad's tick of approval at this Fox Point option which features a garden, a kitchen and more. It has 6 bedrooms that will easily house everyone you love.

What are the best houses for rent with a pool in Chester?

Get set to take your pick and cannonball right in. Here are a couple of popular house rentals in Chester where life is better by the pool:

  • Mum, dad, kids, grandparents — everyone will want to lounge by the pool at "Terraced House With Terrace And Balcony Directly On The Sea And Long Sandy Beach". Take your loved ones on a trip to this Torrox Costa rental home which also comes with a garden and nearby ecotour services.
  • Jump out of bed and take a refreshing early morning dip at "The Little House In Hubbards - A Private Heritage House Steps From The Sea" in Fox Point. Outdoor furniture and pet-friendly facilities are other amenities offered here.

What are the best large family vacation rentals in Chester?

There's nothing like a getaway to bring a family together, but first, you need to find the perfect space. These large family vacation rentals in Chester come with tons of room to stretch out and relax with your loved ones:

  • "4 Bed - - Persons Vacation Rental With Cottage" in Middle River will make your escape a truly memorable one. It has 4 bedrooms sleeping up to 8 people and a range of amenities, including a stereo and coffee and tea making facilities.
  • "Superb Oceanfront With Optional Boathouse" in Canada - New England is another top choice. You'll be able to invite up to 10 people to this getaway which offers 4 bedrooms, a TV, a DVD player and more.

Can I find family cabin rentals in Chester?

If you're planning a trip with the family, pick one of these cabin rentals in Chester and give the kiddos a vacation they'll never forget:

  • "Cabin - Garden Shed Camp @ Off The Beaten Trail" - Escape your daily routine at this Atlantic Provinces retreat which boasts pet-friendly facilities and internet access.
  • "Hilltop Farm Cottage" - Make fond memories with the kiddos at this sought-after hideaway. Located in Canada - New England, it provides guests with free toiletries, outdoor furniture and more.

For more options, use the search bar at the top of the page and adjust the filters to find the Chester vacation rental that's perfect for your needs.

Are there one-bedroom vacation rentals in Chester?

From cute cabins to sprawling mansions and everything in between, we've got properties in every size and shape. If you don't need loads of space, one of our one-bedroom vacation rentals might suit you perfectly:

  • Spend a few lazy days at "A Sailors Paradise - Stevens Cove Guest Quarters" and you'll understand why this one-bedroom rental in Chester is a favorite among guests. A garden and a nearby waterfront are just two of the conveniences that help make this escape a winner.
  • Or, throw your bags down and settle into "Stylish Riverside Country Queen Room In Historic Farmhouse". A garden and a nearby waterfront are just two of the amenities you'll find at this option in Martins River.