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

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chester vacation rentals

A calm lake with a dock and a small building, surrounded by trees.

1. 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 1 - Oct 2
Total with taxes and fees
MV GiaMaria
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

2. 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
Sep 30 - Oct 1
Total with taxes and fees
Cookie B
A marina with docked boats, a covered structure, and a forested hillside in the background.

3. 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, (248 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.
$185 nightly
The price is $211
Sep 30 - Oct 1
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.

4. 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, (124 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
$185 nightly
The price is $211
Sep 30 - Oct 1
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A modern kitchen with a central island, stainless steel appliances, and bar stools.

5. The Studio@ Eanes Drug-Heart of the Historic District

The Studio@ Eanes Drug-Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (99 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
$164 nightly
The price is $187
Sep 30 - Oct 1
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
A hotel room with a bed, a desk with a chair, a television, and a wardrobe.

6. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Petersburg VA
10.0 out of 10, Exceptional, (3 reviews)
"Rooms felt fresh and cozy with everything just right."
United States
Anonymous traveler
$72 nightly
The price is $80
Oct 4 - Oct 5
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

7. 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, (5 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
$194 nightly
The price is $223
Oct 18 - Oct 19
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
A kitchen with a wooden island, stainless steel appliances, and a chandelier.

8. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (5 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
$405 nightly
The price is $409
Sep 30 - Oct 1
Total with taxes and fees
Qualla Park
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

9. 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.
$215 nightly
The price is $247
Oct 1 - Oct 2
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

10. Historic Haven in Church Hill in The Heart of the Historic District

Historic Haven in Church Hill in The Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (80 reviews)
"Nice stay"
United States
Danelle B.
$187 nightly
The price is $213
Oct 11 - Oct 12
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
A wooden gazebo with a bench and string lights, surrounded by trees.

11. Private Garden Home w/ Large Fenced Yard + Gazebo

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (4 reviews)
"Halfway point for our travels up north. Very clean, quiet, everything we needed!"
United States
Tammy K.
$293 nightly
The price is $335
Sep 30 - Oct 1
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

12. 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.
$200 nightly
The price is $203
Oct 19 - Oct 20
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
A modern living room with a teal sofa, a coffee table, and a TV on a stand. There is a 'WELCOME' sign on the wall and a framed picture above the sofa.

13. Lovely 2 Bedroom in the Heart of The Fan

Lovely 2 Bedroom in the Heart of The Fan
Fan District
9.2 out of 10, Wonderful, (88 reviews)
"Great location and very walkable to restaurants, shopping and museums."
United States
Nancy D.
$314 nightly
The price is $334
Sep 30 - Oct 1
Total with taxes and fees
Lovely 2 Bedroom in the Heart of The Fan
A spacious restaurant with high ceilings, large windows, and a central bar area.

14. 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
$154 nightly
The price is $176
Sep 30 - Oct 1
Total with taxes and fees
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
A modern living room with a dark wood floor, a grey sofa, a black coffee table, and a dining area with a green table and chairs.

15. Carytown Family Home Free Parking Fenced Yard

Carytown Family Home Free Parking Fenced Yard
Byrd Park
9.0 out of 10, Wonderful, (20 reviews)
"Great stay! Friendly host and nice location. "
United States
Monte H.
$242 nightly
The price is $265
Oct 7 - Oct 8
Total with taxes and fees
Carytown Family Home Free Parking Fenced Yard
A patio with a wooden deck, a gray outdoor sofa with a yellow pillow, a wooden chair, a small round table, and a spiral staircase leading to a balcony.

16. Colorful private guesthouse in charming Richmond with Parking

Colorful private guesthouse in charming Richmond with Parking
Northern Barton Heights
10.0 out of 10, Exceptional, (6 reviews)
"I like this location. It is close to where I was hanging out in Richmond. The check-in was super easy, and the decorations are fun!"
United States
Jim H.
$190 nightly
The price is $217
Sep 30 - Oct 1
Total with taxes and fees
Colorful private guesthouse in charming Richmond with Parking
A corner building with large windows and a black awning.

17. Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown

Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
Downtown Richmond
9.6 out of 10, Exceptional, (26 reviews)
"The place was clean and tidy, check-in was well organized and friendly, location super convenient."
United States
Maya S.
$153 nightly
The price is $175
Sep 30 - Oct 1
Total with taxes and fees
Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
A modern kitchen with white cabinets, a stainless steel oven, a microwave, and a marble dining table.

18. Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.4 out of 10, Very good, (19 reviews)
"The home was very clean and very comfortable. Communication was excellent. We would definitely stay here again!"
United States
CHRIS
$356 nightly
The price is $399
Oct 5 - Oct 6
Total with taxes and fees
Luxury Stay! 10 min away from Fort Lee.
A living room with a beige sofa, a round black coffee table, a large window, and a painting of a tree.

19. Charming 3-bedroom townhome with WiFi in delightful Richmond

Charming 3-bedroom townhome with WiFi in delightful Richmond
Jahnke
10.0 out of 10, Exceptional, (8 reviews)
"Check-in was simple, good communication, property very much as described/depicted in the listing. Perfect location for our needs. "
United States
Mary C.
$386 nightly
The price is $441
Oct 5 - Oct 6
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
A modern living room with a sofa, a coffee table, and a TV. There is a kitchen in the background with a dining area.

20. Bugalow near Airport - Private Yard, Close to City

Bugalow near Airport - Private Yard, Close to City
Highland Springs
9.6 out of 10, Exceptional, (14 reviews)
"I love my stay feels like home "
United States
LaChandra G.
Bugalow near Airport - Private Yard, Close to City
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

The Commonwealth

The Commonwealth

10/10 Excellent
"We had an excellent stay. The Commonwealth is a perfect combination of new and freshly remodeled, while also offering real charm and historical tradition. We booked a suite, which was fantastic as it allowed out 18-year-old son (who just started his Freshman year at the University of Richmond) to sleep in the pull-out sofa bed on two nights. This allowed my wife and me to spend some great "late night" time catching up with him before we turned in. Anton at the bar was excellent, offering great conversation alongside awesome drinks."
Daniel 4-night trip
Posted 6 hours ago
The Commonwealth

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 $187 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.