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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
The price is CA $300
CA $390 total
includes taxes & fees
Oct 21 - Oct 22
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
The price is CA $308
CA $421 total
includes taxes & fees
Oct 3 - Oct 4
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.
The price is CA $162
CA $301 total
includes taxes & fees
Oct 21 - Oct 22
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, (123 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
The price is CA $162
CA $301 total
includes taxes & fees
Oct 21 - Oct 22
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, (97 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
The price is CA $203
CA $264 total
includes taxes & fees
Sep 27 - Sep 28
The Studio@ Eanes Drug-Heart of the Historic District
A kitchen with a wooden island, stainless steel appliances, and a chandelier.

6. 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.
The price is CA $254
CA $622 total
includes taxes & fees
Sep 27 - Sep 28
Qualla Park
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.
The price is CA $139
CA $317 total
includes taxes & fees
Oct 21 - Oct 22
Newly finished basement suite in Midlothian. Very clean and spacious.
A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

8. 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.
The price is CA $203
CA $264 total
includes taxes & fees
Oct 1 - Oct 2
Historic Haven in Church Hill in The Heart of the Historic District
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

9. 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.
The price is CA $141
CA $292 total
includes taxes & fees
Oct 5 - Oct 6
The Birdhouse - Cozy Cottage Retreat in Richmond
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

10. 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.
The price is CA $133
CA $357 total
includes taxes & fees
Sep 29 - Sep 30
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A hotel room with a bed, a wooden dresser, a television, a desk, and a chair.

11. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Petersburg VA
The price is CA $99
CA $109 total
includes taxes & fees
Sep 27 - Sep 28
2 Queen Beds | Non-Smoking, Micfridge
A wooden gazebo with a bench and string lights, surrounded by trees.

12. 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.
The price is CA $255
CA $553 total
includes taxes & fees
Sep 30 - Oct 1
Private Garden Home w/ Large Fenced Yard + Gazebo
A modern kitchen with a built-in refrigerator, a grey wall with an air conditioning unit, and a staircase leading to a landing.

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

Adorable 2-bedroom house with AC in charming Richmond VA
Richmond
The price is CA $174
CA $255 total
includes taxes & fees
Sep 26 - Sep 27
Adorable 2-bedroom house with AC in charming Richmond VA
A modern kitchen with white cabinets, a stainless steel oven, a microwave, and a marble dining table.

14. 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
The price is CA $218
CA $595 total
includes taxes & fees
Sep 27 - Sep 28
Luxury Stay! 10 min away from Fort Lee.
A spacious restaurant with high ceilings, large windows, and a central bar area.

15. 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
The price is CA $133
CA $266 total
includes taxes & fees
Sep 29 - Sep 30
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
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.

16. 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.
The price is CA $161
CA $499 total
includes taxes & fees
Oct 21 - Oct 22
Lovely 2 Bedroom in the Heart of The Fan
A two-story house with a front deck, a small porch, and a backyard with a trampoline and a grill.

17. 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.
The price is CA $183
CA $324 total
includes taxes & fees
Sep 30 - Oct 1
Private bedroom and bath!
A living room with a sofa, two armchairs, a coffee table, and a rug. There are two windows with blinds, a door, and a wall-mounted light fixture.

18. The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6

The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6
Woodhaven
The price is CA $259
CA $591 total
includes taxes & fees
Sep 27 - Sep 28
The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6

19. Oaks Retreat Carytown House Family Pet Friendly

Oaks Retreat Carytown House Family Pet Friendly
Randolph
9.0 out of 10, Wonderful, (20 reviews)
"Great quiet area, easy access to downtown and close to restaurants and parks. Nicely set up home with exceptional comforts for all"
United States
Thomas C.
The price is CA $175
CA $389 total
includes taxes & fees
Sep 27 - Sep 28
Oaks Retreat Carytown House Family Pet Friendly
A gray sectional sofa with patterned cushions, a white door, decorative wall art, a window with blinds, and a small table with a lamp.

20. 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.
The price is CA $146
CA $282 total
includes taxes & fees
Sep 28 - Sep 29
The Fan Comfort Stay near VCU Free Parking Fenced Yard
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
"Beautiful place with helpful, friendly staff. I will come back."
Lee Ann 2-night trip
Posted 1 hour 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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester vacation rentals we have selected for you start as low as CA $264 per night. Entering your travel dates in the search wizard 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.

What's the top vacation rental in Chester?

Fantastic 5-bedroom Luxury home in charming Richmond: This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.