Chester Vacation Rentals

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Vacation Rentals in Chester

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
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
Jun 18 - Jun 19
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
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!
Downtown Living in Richmond's Amazing Shockoe Bottom
Fridge, microwave, oven, stovetop
Downtown Living in Richmond's Amazing Shockoe Bottom
9.8 out of 10, Exceptional, (13)
"Exactly as described and in a nice and convenient location"
The price is $121
$258 total
includes taxes & fees
Jun 17 - Jun 18
Downtown Living in Richmond's Amazing Shockoe Bottom
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Downtown Living in Historic Richmond Loft
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
Jun 3 - Jun 4
Downtown Living in Historic Richmond Loft
Cozy Cape Cod Home!
Smart TV
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, (25)
"Great rental! The owner was punctual with communication and the home met our needs."
Cozy Cape Cod Home!
Lovely 2 Bedroom in the Heart of The Fan
Fridge, microwave, oven, stovetop
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, (35)
"Super cute and roomy, hosts were super helpful and quick to respond! "
The price is $156
$302 total
includes taxes & fees
Jun 3 - Jun 4
Lovely 2 Bedroom in the Heart of The Fan
The lake house at lake chesdin
Smart TV, fireplace
The lake house at lake chesdin
10.0 out of 10, Exceptional, (3)
"Older home but well maintained. View of the lake was gorgeous, especially with the setting sun. Thanks!"
The price is $355
$489 total
includes taxes & fees
Jun 2 - Jun 3
The lake house at lake chesdin
The Bike Path House! Cozy 2 BR w/ Fireplace
Property grounds
The Bike Path House! Cozy 2 BR w/ Fireplace
9.4 out of 10, Exceptional, (9)
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
Magnolias, a chill out place.
Exterior
Magnolias, a chill out place.
10.0 out of 10, Exceptional, (7)
"Magnolias is exactly what it is advertising. A great place to stay for a few nights when visiting RVA. Super close to the RIC. Easy to get to and from downtown. Very comfortable. Well worth the price."
The price is $69
$124 total
includes taxes & fees
Jun 26 - Jun 27
Magnolias, a chill out place.
Modern, Lovely and Spacious Home
Exterior
Modern, Lovely and Spacious Home
10.0 out of 10, Exceptional, (9)
"This is a lovely home with the charm of years gone by and located in historic Jackson Ward. It is in easy walking distance from numerous restaurants, shops, and the contemporary art museum. The hostess was in regular communication with us to ensure we had a great stay."
Modern, Lovely and Spacious Home
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Property grounds
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (170)
"We needed a place to stay while in town for nephew’s graduation. This house was the perfect solution! Location was just 10 min from the family we were visiting and less than 5 min to grocery and coffee. Very sweet older neighborhood. Very convenient and cozy home."
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
Fridge, microwave, oven, stovetop
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
9.8 out of 10, Exceptional, (7)
"We appreciated that the landlord allowed us to check in early. Like many ABNB properties, the inside is not quite as nice as the pictures. It’s barely four stars in my opinion. The outside is rough and so is the neighborhood, however that was relatively clear from the photos before we arrived. The appliances were new. Overall not a bad property but it needs work, particularly on the outside."
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Interior
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
10.0 out of 10, Exceptional, (43)
"My husband and I stayed in Richmond for a long weekend and lucked onto this beautiful condo in downtown. We are fans of old buildings and this one was old but still in great shape, very nicely kept up and included all the amenities we needed. The condo had 3 huge street- facing windows that admitted Plenty of light and made for some fun watching of the street scene below. Check in was seamless and the hosts were super responsive. We had to keep moving our car around in order to obtain reasonable...
The price is $99
$207 total
includes taxes & fees
Jun 2 - Jun 3
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Lovely 1-Bedroom Loft with Free Parking and Wifi
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
Jun 3 - Jun 4
Lovely 1-Bedroom Loft with Free Parking and Wifi
Recline at Timberline! Family friendly!
Fridge, microwave, oven, stovetop
Recline at Timberline! Family friendly!
9.4 out of 10, Exceptional, (25)
"Location is convenient for visiting the Richmond area. Neighborhood is quiet. House is nice but needs some updating."
The price is $125
$311 total
includes taxes & fees
Jun 3 - Jun 4
Recline at Timberline! Family friendly!
Industrial Chic Loft in the Heart of Downtown Richmond!
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!
Richmond Home w/ Fire Pit - 12 Mi to Downtown
Fridge, microwave, stovetop, dishwasher
Richmond Home w/ Fire Pit - 12 Mi to Downtown
10.0 out of 10, Exceptional, (9)
"Convenient to Broad St.and Parham St. in Richmond. Easy access to everything."
Richmond Home w/ Fire Pit - 12 Mi to Downtown
Newly Renovated Historic Home < 2 Mi to Downtown!
Fridge, microwave, stovetop, dishwasher
Newly Renovated Historic Home < 2 Mi to Downtown!
9.8 out of 10, Exceptional, (47)
"Enjoyed our time"
Newly Renovated Historic Home < 2 Mi to Downtown!
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
Exterior
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
9.6 out of 10, Exceptional, (8)
"5-star Highly Recommend! Couldn’t have picked a better location for graduation weekend. Central location close to everything. Seamless check-in/check-out. Owner was great to work with, extremely accommodating, and immediately responded to every question I had. Thanks again!"
The price is $113
$342 total
includes taxes & fees
Jun 2 - Jun 3
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
Terre Haute Manor Farmhouse w/ Gardens & Deck!
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!
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

SpringHill Suites Chester
Property amenity
SpringHill Suites Chester
2.5 star property
9.0 out of 10, Wonderful, (310)
"Really nice room no complaints whatsoever, quiet, comfortable, clean, s/other really liked the separate area where he could get on his laptop without disturbing me while I was sleeping. Will definitely consider staying at this facility again "
The price is $125
$145 total
includes taxes & fees
Jun 13 - Jun 14
SpringHill Suites Chester
Country Inn & Suites by Radisson, Chester, VA
Lobby
Country Inn & Suites by Radisson, Chester, VA
3.0 star property
7.0 out of 10, Good, (1006)
"Great stay! "
The price is $106
$123 total
includes taxes & fees
Jul 1 - Jul 2
Country Inn & Suites by Radisson, Chester, VA
Red Roof Inn Chester
Lobby
Red Roof Inn Chester
2.0 star property
7.0 out of 10, Good, (512)
"It a good place for the price."
The price is $74
$86 total
includes taxes & fees
Jun 5 - Jun 6
Red Roof Inn 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.

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

Best Western Plus Richmond Airport Hotel

Best Western Plus Richmond Airport Hotel

5/5 Excellent
" location, restaurants, free awesome breakfast, comfortable room, clean, awesome staff, price. - large hole in carpet in room…worn through"
A verified traveler from Washington stayed at Best Western Plus Richmond Airport Hotel
Posted 13 hours ago
Best Western Plus Richmond Airport Hotel