Chester Holiday Rentals

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Holiday Rentals in Chester

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 NZ$203
includes taxes & fees
3 Jun - 4 Jun
Magnolias, a chill out place.
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 NZ$320
includes taxes & fees
29 May - 30 May
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
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 NZ$523
includes taxes & fees
28 May - 29 May
Downtown Living in Historic Richmond Loft
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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!
Fridge, microwave, oven, stovetop
Lovely 2 Bedroom in the Heart of The Fan
9.4 out of 10, Exceptional, (35)
"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 NZ$493
includes taxes & fees
29 May - 30 May
Lovely 2 Bedroom in the Heart of The Fan
Property grounds
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (169)
"Quickly felt like “home” for dog and people! Comfortable location with easy access to restaurants and stores. Will definitely stay here again when visiting Richmond!"
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Private kitchen
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!
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!
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
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 NZ$423
includes taxes & fees
10 Jun - 11 Jun
Downtown Living in Richmond's Amazing Shockoe Bottom
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
Terrace/patio
Modern Unit in Historic Old Manchester.
10.0 out of 10, Exceptional, (22)
"We had a great time at this location. Close to everything and very clean. Had everything that we needed. Very comfortable beds. Made us feel like we were at home. Will definitely try to stay here next time in town."
Modern Unit in Historic Old Manchester.
Terrace/patio
Central location w/ large fenced yard FIRE-PIT
10.0 out of 10, Exceptional, (22)
"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...
The price is NZ$417
includes taxes & fees
28 May - 29 May
Central location w/ large fenced yard FIRE-PIT
4 bedrooms, iron/ironing board, free WiFi, bed sheets
The Cozy Rancher | Petersburg | King Bed
10.0 out of 10, Exceptional, (21)
"We loved this property it was truly a home away from home. This house was clean, decorative, nice clean smell, and located in a quite neighborhood. It was truly relaxing and made us feel right at home."
The price is NZ$578
includes taxes & fees
28 May - 29 May
The Cozy Rancher | Petersburg | King Bed
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 NZ$423
includes taxes & fees
28 May - 29 May
Lovely 1-Bedroom Loft with Free Parking and Wifi
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
Fridge, microwave, stovetop, dishwasher
Richmond Home w/ Fire Pit - 12 Mi to Downtown
10.0 out of 10, Exceptional, (7)
"We had a wonderful stay at this property -- it was exactly as advertised. It was spotlessly clean, the beds were comfortable, it had all needed amenities, and it was in a great location. I highly recommend it."
Richmond Home w/ Fire Pit - 12 Mi to Downtown
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 NZ$683
includes taxes & fees
29 May - 30 May
The lake house at lake chesdin
Fridge, microwave, stovetop, dishwasher
Newly Renovated Historic Home < 2 Mi to Downtown!
9.8 out of 10, Exceptional, (47)
"It was perfect for the board members to stay together, away from the conference center, room to relax and solve the little problems that arise, away from the exhibition hall. Enough seating space for everyone involved for dinners and relaxation. Great for large group discussions and small group conversations."
Newly Renovated Historic Home < 2 Mi to Downtown!
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.

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, (1001)
"Very clean"
The price is NZ$197
includes taxes & fees
2 Jun - 3 Jun
Country Inn & Suites by Radisson, Chester, VA
Property amenity
SpringHill Suites Chester
2.5 star property
9.0 out of 10, Wonderful, (304)
"Nice "
The price is NZ$251
includes taxes & fees
3 Jun - 4 Jun
SpringHill Suites Chester
Seasonal outdoor pool
Comfort Inn Chester - Richmond South
2.5 star property
7.8 out of 10, Good, (904)
"Had same breakfast everyday. Change it up. "
The price is NZ$165
includes taxes & fees
30 May - 31 May
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.

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