An aerial view of a residential area with houses, roads, and a water tower.

Chester Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chester vacation rentals

A marina with docked boats, a covered structure, and a forested hillside in the background.

1. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (249 reviews)
"We had a great stay! Perfect get away for our anniversary. It had everything we needed and was super quiet with a great view. Thank you Captain Ron, for an amazing experience "
United States
Allison K.
$189 nightly
The price is $216
Oct 12 - Oct 13
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

2. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (125 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
$188 nightly
The price is $215
Oct 8 - Oct 9
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

3. Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (9 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
$263 nightly
The price is $299
Oct 7 - Oct 8
Total with taxes and fees
Cookie B
A calm lake with a dock and a small building, surrounded by trees.

4. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.2 out of 10, Wonderful, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
$243 nightly
The price is $277
Oct 7 - Oct 8
Total with taxes and fees
MV GiaMaria
A reception desk with a computer, a telephone, and a small plant.

5. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Petersburg VA
10.0 out of 10, Exceptional, (4 reviews)
"Clean rooms with quick service!"
United States
Anonymous traveler
$67 nightly
The price is $74
Oct 7 - Oct 8
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

6. Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Chesterfield
10.0 out of 10, Exceptional, (7 reviews)
"Quiet and Cozy. Beautiful scenery, great walking trails. Host was extra accomdating with check-in and out process. Would definitely visit again "
United States
G H.
$220 nightly
The price is $253
Oct 7 - Oct 8
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

7. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (6 reviews)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
$206 nightly
The price is $209
Oct 19 - Oct 20
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
A room with a fireplace, a mirror above it, and two leather chairs.

8. Nest & Rest | Private Studio | Free Parking

Nest & Rest | Private Studio | Free Parking
Fan District
9.8 out of 10, Exceptional, (46 reviews)
"Host was gracious and responsive, and the location was amazing! "
United States
Kelly M.
$133 nightly
The price is $148
Oct 20 - Oct 21
Total with taxes and fees
Nest & Rest | Private Studio | Free Parking
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

9. Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (6 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
$197 nightly
The price is $227
Oct 26 - Oct 27
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
A corner building with large windows and a black awning.

10. RVA Arts District near VCU MCV

RVA Arts District near VCU MCV
Downtown Richmond
9.6 out of 10, Exceptional, (28 reviews)
"Great spot above the coolest music store in downtown Richmond. Easy stay and very enjoyable!"
United States
Benjamin
RVA Arts District near VCU MCV
A corner building with large windows and a black awning.

11. New Heart of the Arts District Condo Downtown near MCV VCU Convention Center

New Heart of the Arts District Condo Downtown near MCV VCU Convention Center
Downtown Richmond
9.6 out of 10, Exceptional, (18 reviews)
"Clean, great location, and check-in and check-out were very easy!"
United States
Claire N.
New Heart of the Arts District Condo Downtown near MCV VCU Convention Center
A gray sectional sofa with patterned cushions, a white door, decorative wall art, a window with blinds, and a small table with a lamp.

12. The Fan Comfort Stay near VCU Free Parking Fenced Yard

The Fan Comfort Stay near VCU Free Parking Fenced Yard
Fan District
9.4 out of 10, Exceptional, (30 reviews)
"Very convenient location, and great communication!"
United States
Katelyn F.
$182 nightly
The price is $202
Oct 12 - Oct 13
Total with taxes and fees
The Fan Comfort Stay near VCU Free Parking Fenced Yard
A room with a sofa, a coffee table, a dining table with chairs, a window with a 'Thank You' sign, and a view of trees.

13. 2 Full Beds|Non-Smoking

2 Full Beds|Non-Smoking
Petersburg VA
10.0 out of 10, Exceptional, (81 reviews)
"Appreciated the cozy lounge area, made relaxing after a long day easy."
United States
Anonymous traveler
$58 nightly
The price is $65
Oct 7 - Oct 8
Total with taxes and fees
2 Full Beds|Non-Smoking
A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

14. Private bedroom and bath!

Private bedroom and bath!
Midlothian
6.0 out of 10, (2 reviews)
"We had a lacrosse tournament at River city sports plex. This was perfect location to stay for us. Friendly and amazing combination with host. Extremely pleased with our stay"
United States
Ridge W.
$203 nightly
The price is $234
Oct 7 - Oct 8
Total with taxes and fees
Private bedroom and bath!
A modern kitchen with stainless steel appliances, a white countertop, and pendant lighting.

15. Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (35 reviews)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
$307 nightly
The price is $328
Oct 12 - Oct 13
Total with taxes and fees
Downtown Living in Richmond's Amazing Shockoe Bottom
A bedroom with a bed, a TV, and built-in shelving with decorative items.

16. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (24 reviews)
"Would stay again!"
United States
Amir D.
$105 nightly
The price is $120
Oct 12 - Oct 13
Total with taxes and fees
Magnolias, a chill out place.
A high-ceilinged interior with skylights and built-in shelving.

17. Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU

Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
Downtown Richmond
9.8 out of 10, Exceptional, (56 reviews)
"Great stay."
United States
Brian D.
$180 nightly
The price is $206
Oct 27 - Oct 28
Total with taxes and fees
Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
A hotel room with two beds, a window with a view of parked cars, a wooden headboard, and a framed picture on the wall.

18. 2 Full Bed|Smoking|Petersburg VA

2 Full Bed|Smoking|Petersburg VA
Petersburg VA
10.0 out of 10, Exceptional, (81 reviews)
"Cozy spot with friendly staff."
United States
Anonymous traveler
$58 nightly
The price is $65
Oct 7 - Oct 8
Total with taxes and fees
2 Full Bed|Smoking|Petersburg VA
A compact living space with a kitchenette, a sofa, and a television.

19. Adorable 2-bedroom house with AC in charming Richmond VA

Adorable 2-bedroom house with AC in charming Richmond VA
Richmond
10.0 out of 10, Exceptional, (1 review)
"Sloan was/is easy to work with and was veryaccommodating. Communication with Sloan was easy and fast! The property was clean and well furnished."
United States
Jim S.
$158 nightly
The price is $181
Oct 12 - Oct 13
Total with taxes and fees
Adorable 2-bedroom house with AC in charming Richmond VA
A spacious restaurant with high ceilings, large windows, and a central bar area.

20. Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Downtown Richmond
9.8 out of 10, Exceptional, (92 reviews)
"Just a great space to stay very comfortable and the location is awesome - many nearby clubs bars and places to eat! Have stayed 4 times and one of my favorite places to stay anywhere"
United States
rob
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
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.
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Top Chester Hotel Reviews

Linden Row Inn

Linden Row Inn

10/10 Excellent
"Specious room with nice bath. It was very quiet! Close to everything we planned to visit."
Natalie 2-night trip
Posted 1 day ago
Linden Row Inn

Find out more about Chester

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 $195 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.

Explore a world of travel with Expedia

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?

Spacious 4-bedroom house in awesome Midlothian with AC: This vacation home rental outside of Chester offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Chester?

With 8 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. Dutch Gap Conservation Area and Point of Rocks 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.