Chester Vacation Rentals

Vacation Rentals in Chester

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
9.6 out of 10, Exceptional, 192 reviews
"Charming host, unique property on the St James River, very relaxing setting."
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Downtown Living in Richmond's Amazing Shockoe Bottom
9.8 out of 10, Exceptional, 13 reviews
"Exactly as described and in a nice and convenient location"
Downtown Living in Richmond's Amazing Shockoe Bottom
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
10.0 out of 10, Exceptional, 9 reviews
"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!
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Newly Renovated Historic Home < 2 Mi to Downtown!
9.8 out of 10, Exceptional, 47 reviews
"Enjoyed our time"
Newly Renovated Historic Home < 2 Mi to Downtown!
G6 Central location STUDIO museums FREE PARKING
10.0 out of 10, Exceptional, 19 reviews
"We had a great time staying here. My sister and I ran the Monument 10K and it was an ideal location, just a short walk to the start line. We would absolutely stay here again!"
G6 Central location STUDIO museums FREE PARKING
Central location w/ large fenced yard FIRE-PIT
10.0 out of 10, Exceptional, 22 reviews
"This was a wonderful home and a fantastic experience. The host was perfectly communicative, the check in process was simple and seamless. The house was clean and comfortable, stocked with everything we needed- including a functioning grill and a stockpile of wood for fires out back, which we had one every single night. We had four adults and three children, and there was plenty of space between the rooms. The beds were comfortable and having a large TV in the living room preset with streaming...
Central location w/ large fenced yard FIRE-PIT
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
9.8 out of 10, Exceptional, 7 reviews
"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
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, 25 reviews
"Great rental! The owner was punctual with communication and the home met our needs."
Cozy Cape Cod Home!
Magnolias, a chill out place.
10.0 out of 10, Exceptional, 7 reviews
"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."
Magnolias, a chill out place.
The lake house at lake chesdin
10.0 out of 10, Exceptional, 6 reviews
"Our first time staying at this property. So glad we found it - it will be our first choice for future trips to Chesdin. The house is spacious and wonderfully appointed. Kitchen has everything you'll need. Plenty of parking (we had 2 boats/trucks). The neighborhood is quiet and safe. House sits right on the water w/ a fabulous view of the sunset. This place is great for a family get-away or homebase for a fishing trip. Minutes to the Whippernock ramp."
The lake house at lake chesdin
Downtown Living in Historic Richmond Loft
8.4 out of 10, Very Good, 41 reviews
"Wonderful apartment, plenty of room for us and located near many things to do!"
Downtown Living in Historic Richmond Loft
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
10.0 out of 10, Exceptional, 43 reviews
"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...
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Lovely 1-Bedroom Loft with Free Parking and Wifi
8.8 out of 10, Excellent, 9 reviews
"In the city. Good neighborhood"
Lovely 1-Bedroom Loft with Free Parking and Wifi
Industrial Chic Loft in the Heart of Downtown Richmond!
9.8 out of 10, Exceptional, 7 reviews
"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!
The Happy Place, Kingsize bed.
9.6 out of 10, Exceptional, 4 reviews
"The listing was as depicted. The owner was very responsive and answered all our questions. She even brought us a new coffee pot!"
The Happy Place, Kingsize bed.
The Bike Path House! Cozy 2 BR w/ Fireplace
9.4 out of 10, Exceptional, 9 reviews
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
Richmond Home w/ Fire Pit - 12 Mi to Downtown
10.0 out of 10, Exceptional, 9 reviews
"Convenient to Broad St.and Parham St. in Richmond. Easy access to everything."
Richmond Home w/ Fire Pit - 12 Mi to Downtown
Terre Haute Manor Farmhouse w/ Gardens & Deck!
10.0 out of 10, Exceptional, 19 reviews
"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!
Cedar Lane Plantation dated back to early 1809
10.0 out of 10, Exceptional, 25 reviews
"The home was amazing and we appreciated the decor and specific details that were from the 1800’s. We felt in history in the home. The bedrooms with bathrooms were amazingly decorated and the kitchen was well stocked! Thank you for sharing your home with us."
Cedar Lane Plantation dated back to early 1809
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, 171 reviews
"Thanks Josh! Brought back so many memories!!"
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
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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

Other types of properties in Chester you may be interested in

SpringHill Suites Chester
2.5 star property
9.0 out of 10, Wonderful, 318 reviews
"Nice clean hotel in a good location! Staff was very helpful and courteous, will def stay again!"
SpringHill Suites Chester
Country Inn & Suites by Radisson, Chester, VA
3.0 star property
7.0 out of 10, Good, 1,012 reviews
"The room was appropriate for Stay"
Country Inn & Suites by Radisson, Chester, VA
Red Roof Inn Chester
2.0 star property
7.0 out of 10, Good, 516 reviews
"Surprisingly good condition facility for a budget hotel. It was a little hard to find but had fast food and convenience stores within easy walking distance. Surprisingly quiet for such a busy area. Breakfast choices were weak. Police came in to speak with some guests as I was checking in so that put me on the defensive, but by the time ingot to my room, I felt safe. "
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 CNY812 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.

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.

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