Chester Holiday Rentals

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Holiday 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
"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 NZ$315
includes taxes & fees
30 Jun - 1 Jul
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
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!
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"
The price is NZ$419
includes taxes & fees
1 Jul - 2 Jul
Downtown Living in Richmond's Amazing Shockoe Bottom
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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!"
The price is NZ$517
includes taxes & fees
1 Jul - 2 Jul
Downtown Living in Historic Richmond Loft
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!
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, 35 reviews
"Super cute and roomy, hosts were super helpful and quick to respond! "
The price is NZ$490
includes taxes & fees
5 Jun - 6 Jun
Lovely 2 Bedroom in the Heart of The Fan
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 price is NZ$728
includes taxes & fees
6 Jun - 7 Jun
The lake house at lake chesdin
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
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."
The price is NZ$201
includes taxes & fees
28 Jun - 29 Jun
Magnolias, a chill out place.
Modern, Lovely and Spacious Home
10.0 out of 10, Exceptional, 9 reviews
"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!
10.0 out of 10, Exceptional, 171 reviews
"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
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
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...
The price is NZ$338
includes taxes & fees
5 Jun - 6 Jun
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"
The price is NZ$419
includes taxes & fees
1 Jul - 2 Jul
Lovely 1-Bedroom Loft with Free Parking and Wifi
Recline at Timberline! Family friendly!
9.4 out of 10, Exceptional, 26 reviews
"We were very comfortable in your home. It was a great location and just what we needed for our family"
Recline at Timberline! Family friendly!
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!
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
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!
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
9.6 out of 10, Exceptional, 9 reviews
"We enjoyed our stay here! It was clean, cheery and comfortable and close to everything we needed. 6 min walk to the Convention Center. The only negative really is the first impression from the street. The apartment is on the 2nd floor and is only accessible from a private parking lot beside the building and up a big set of wooden stairs. At first appearance, we were a little nervous because we didn't know the area, etc. But once we climbed those stairs, we realized we were in a safe area and...
The price is NZ$546
includes taxes & fees
5 Jun - 6 Jun
Bright & Cozy Downtown Apartment - Free Parking - Dogs Welcome - Fast Wi-Fi
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!
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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.

Other types of properties in Chester you may be interested in

SpringHill Suites Chester
2.5 star property
9.0 out of 10, Wonderful, 315 reviews
"Love the front desk people."
The price is NZ$248
includes taxes & fees
12 Jun - 13 Jun
SpringHill Suites Chester
Country Inn & Suites by Radisson, Chester, VA
3.0 star property
7.0 out of 10, Good, 1,008 reviews
"The room was appropriate for Stay"
The price is NZ$200
includes taxes & fees
30 Jun - 1 Jul
Country Inn & Suites by Radisson, Chester, VA
Red Roof Inn Chester
2.0 star property
7.0 out of 10, Good, 516 reviews
"Room was clean, i got what i paid for and most important no bugs"
The price is NZ$139
includes taxes & fees
10 Jun - 11 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chester. Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chester short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Chester?

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

How many holiday rentals are there in Chester?

With 3 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.

Recent reviews of Chester properties
Expedia verified reviews