Chester Vacation Rentals

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Vacation Rentals in Chester

Property grounds
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
9.6 out of 10, Exceptional, (191)
"We had an enjoyable stay on the houseboat. The bed was comfortable, and the accommodations had everything we needed. We even made spaghetti the first night for dinner since we arrived later than planned. The area is private, we only saw a few people and those we did see gave a friendly hello if they didn't stop to chat with us. For anyone wondering about the movement of the boat, it is very stable. The boat is docked in a channel off the main river so not a lot of boat traffic and the currents...
The price is $100
$196 total
includes taxes & fees
May 21 - May 22
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Exterior
Magnolias, a chill out place.
10.0 out of 10, Exceptional, (7)
"Pleasant host"
The price is $69
$124 total
includes taxes & fees
May 20 - May 21
Magnolias, a chill out place.
Fridge, microwave, oven, stovetop
Downtown Living in Historic Richmond Loft
8.4 out of 10, Very Good, (41)
"Wonderful apartment, plenty of room for us and located near many things to do!"
The price is $156
$320 total
includes taxes & fees
May 22 - May 23
Downtown Living in Historic Richmond Loft
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Fridge, microwave, oven, stovetop
Downtown Living in Richmond's Amazing Shockoe Bottom
9.8 out of 10, Exceptional, (12)
"Clean loft. Walkable location to restaurants and things to do."
The price is $121
$259 total
includes taxes & fees
May 20 - May 21
Downtown Living in Richmond's Amazing Shockoe Bottom
Fridge, microwave, oven, stovetop
Lovely 1-Bedroom Loft with Free Parking and Wifi
8.8 out of 10, Excellent, (9)
"In the city. Good neighborhood"
The price is $121
$259 total
includes taxes & fees
May 20 - May 21
Lovely 1-Bedroom Loft with Free Parking and Wifi
Fridge, microwave, oven, stovetop
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, (34)
"We really liked our apartment. It was clean and comfortable and the location was perfect. There were only 2 issues. The water pressure in the bathroom was extremely low. And the neighbor upstairs was SO loud. They had loud conversations until around 2 AM, heavy footsteps, and an extremely loud TV that stayed on all night until 4 AM. It was almost impossible to sleep."
The price is $156
$302 total
includes taxes & fees
May 21 - May 22
Lovely 2 Bedroom in the Heart of The Fan
Fridge, microwave, oven, stovetop
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
10.0 out of 10, Exceptional, (9)
"This is the place for you and yours! We came to Richmond to see the sites and tour civil war era places. It was always so nice to come "home""
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
Property grounds
Stunning! River-Front Log Cabin Near Williamsburg
9.8 out of 10, Exceptional, (30)
"It was peaceful & amazing! Love the place!"
Stunning! River-Front Log Cabin Near Williamsburg
Property grounds
The Bike Path House! Cozy 2 BR w/ Fireplace
10.0 out of 10, Exceptional, (8)
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
Smart TV
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, (24)
"We stayed at the house for a long weekend for our son’s lacrosse game at The University of Richmond. The house was clean and was exactly as pictured. The fire pit in the back was a nice plus and we really liked the lights above it. The house was close to many stores and an easy ride to other locations in Richmond."
Cozy Cape Cod Home!
Exterior
Industrial Chic Loft in the Heart of Downtown Richmond!
9.8 out of 10, Exceptional, (7)
"I loved it was so close to everything history this place was amazing and will be back in the future "
Industrial Chic Loft in the Heart of Downtown Richmond!
Private kitchen
Cozy and Family-Sized RVA Haven located near Short Pump Mall
8.0 out of 10, Very Good, (1)
"Property and stay was great. Had issues with access to check in and communication with owner. Getting code to gain access and checking in took 2 hours. Owner did reimburse $68 for dinner. Overall positive experience."
The price is $230
$352 total
includes taxes & fees
May 19 - May 20
Cozy and Family-Sized RVA Haven located near Short Pump Mall
Fridge, microwave, oven, stovetop
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
10.0 out of 10, Exceptional, (6)
"We were very happy with our stay."
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
Private kitchen | Fridge, microwave, oven, stovetop
Brand New, Gorgeous Studio Close to Everything!
10.0 out of 10, Exceptional, (25)
"Cleanliness was outstanding; we appreciated the thoughtfulness of the water bottles and the wine; excellent soap/hair products; very appealing decor; the bed was very comfortable, especially when we used the additional mattress pad. One wrinkle for us was the challenge of pulling out the sofa to bed conversion. Once we did that and added the padding from the closet, sleeping was great. We were so impressed with how you utilized the space and how you thought of everything we could want. Also,...
Brand New, Gorgeous Studio Close to Everything!
Fridge, microwave, oven, stovetop
Serenity in the Suburbs: Your Gorgeous RVA Getaway
9.4 out of 10, Exceptional, (9)
"The house was very convenient to Pocahontas State park. Tucked into a secluded area, we didn't feel like we were in the suburbs at all. Large yard, common spaces, and amenities made this a nice house for bigger groups."
Serenity in the Suburbs: Your Gorgeous RVA Getaway
Fridge, microwave, stovetop, dishwasher
Terre Haute Manor Farmhouse w/ Gardens & Deck!
10.0 out of 10, Exceptional, (19)
"I took two teams (UMASS & JMU) to the college super regional Pickleball tournament. The house was fantastic because it was affordable for college kids (though one needed to be 30 years of age to book it…I exceed that age), it had lots of beds and enough bathrooms and a kitchen. I recommend getting there in the daylight hours because it is a little off the beaten path and dark when you arrive but it was perfect fit for our needs - great hospitality! Beautiful animals in the property too (donkeys...
Terre Haute Manor Farmhouse w/ Gardens & Deck!
Exterior
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
9.6 out of 10, Exceptional, (7)
"This location was a short walk to the convention center which was perfect for us. So much more spacious than a hotel. The beds were comfortable. The white noise alarm clocks in the bedrooms were perfect for blocking out the street noise. The only thing we would have liked to have that we didn’t was a toaster in the kitchen. We will stay again if attending events at the convention center."
The price is $116
$345 total
includes taxes & fees
May 28 - May 29
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
Interior
Relaxing Place!
9.8 out of 10, Exceptional, (26)
"Fantastic accommodations, very spacious and clean. Could sleep a lot of people if needed but extremely comfortable for the 4 we had."
Relaxing Place!
Property grounds
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (167)
"This is our go to in Richmond. Always great. Thanks Josh."
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Exterior
Modern, Lovely and Spacious Home
10.0 out of 10, Exceptional, (8)
"We stay in a number of rentals on our vacations, and this one was top notch with all the small things provided, paper towels/toilet paper/dish soap etc. Proximity to VCU Medical Center, and all the wonderful downtown areas is incredible. The host reached out a number of times checking in to see if we needed anything and hoping we were having a good stay. He was wonderful! The house had an incredible coziness to it and we all felt at home. The beds were comfortable. The towels were great. The...
Modern, Lovely and Spacious Home
Don't see what you're looking for?
See all available properties in Chester
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.

Chester Vacation Rental Travel Info

Number of vacation rentals
5
Known landmarks
Keystone Antique Truck and Tractor Museum, Iron Bridge Sports Park and Swift Creek Mill Theatre
International airport
Richmond, VA (RIC-Richmond Intl.)

Other types of properties in Chester you may be interested in

Lobby
Country Inn & Suites by Radisson, Chester, VA
3.0 star property
7.0 out of 10, Good, (1000)
"It was very crowded with children and no adults with them at the breakfast area "
The price is $98
$114 total
includes taxes & fees
Jun 9 - Jun 10
Country Inn & Suites by Radisson, Chester, VA
Property amenity
SpringHill Suites Chester
2.5 star property
9.0 out of 10, Wonderful, (290)
"Clean, quiet, good breakfast"
The price is $132
$153 total
includes taxes & fees
May 27 - May 28
SpringHill Suites Chester
Seasonal outdoor pool
Comfort Inn Chester - Richmond South
2.5 star property
7.8 out of 10, Good, (897)
"I enjoyed the quiet and clean room I had. They also provided a breakfast that me and my son enjoyed. "
The price is $80
$93 total
includes taxes & fees
May 19 - May 20
Comfort Inn Chester - Richmond South
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.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $69 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, there are vacation rentals in Chester close to Iron Bridge Sports Park, or you can select a more secluded option if you want a relaxing stay. Visitors like the top-notch restaurants and shops in Chester. Make sure you have time to check out the art and cafes during your trip.

What's the top vacation rental in Chester?

Gorgeously Renovated 3500 square foot Oxford home in Richmond!!: This vacation home rental outside of Chester is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the arcade game room in this rental home to help you unwind.

How many vacation rentals are there in Chester?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Chester stay.

What’s there to see and do in Chester?

Family-friendly attractions include Iron Bridge Sports Park and The Lazy Daisy, whereas James River and Henricus Historical Park are a couple of great spots to enjoy the outdoors. Appomattox River and Parker's Battery Park are other places to visit while you're in town.

What’s a vacation rental in Chester like?

A vacation rental is a private property you can book for several days or longer in Chester. Vacation rentals feature amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for small groups.

Recent reviews of Chester properties
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

La Quinta Inn & Suites by Wyndham Richmond-Midlothian

5/5 Excellent
"Smelled fresh and clean"
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Richmond-Midlothian
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Richmond-Midlothian