Chester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chester vacation rentals

A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

1. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
The price is CA $170
CA $489 total
includes taxes & fees
Nov 15 - Nov 16
Game Room + Yard: Updated House in Chester!
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

2. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
Chester
9.0 out of 10, Wonderful, (4 reviews)
"Great stay. Super clean! Great communication with host. 30 mins from Richmond VA, great for exploring surrounding areas!"
United States
Akia S.
The price is CA $117
CA $483 total
includes taxes & fees
Nov 15 - Nov 16
Game Room + Yard: Updated House in Chester!
A compact living area with a blue sofa, a purple armchair, and a small table with a checkered edge.

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, (252 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 $289 total
includes taxes & fees
Nov 9 - Nov 10
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A cozy living room with a television, a fireplace, a Coca-Cola branded stool, and a patterned rug.

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, (126 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
The price is CA $162
CA $289 total
includes taxes & fees
Nov 9 - Nov 10
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A hotel room with a large bed, a window with a view of boats, a lamp, and framed pictures on the wall.

5. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.4 out of 10, Exceptional, (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 $302
CA $392 total
includes taxes & fees
Nov 9 - Nov 10
MV GiaMaria
A boat with a cabin, a small deck area with a ramp, and a docked boat in the background.

6. Cookie B

Cookie B
3.0 star property
Richmond
9.2 out of 10, Wonderful, (10 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 $309
CA $423 total
includes taxes & fees
Nov 9 - Nov 10
Cookie B
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

7. 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 traveller
The price is CA $97
CA $107 total
includes taxes & fees
Nov 12 - Nov 13
2 Queen Beds | Non-Smoking, Micfridge
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

8. 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.
The price is CA $155
CA $322 total
includes taxes & fees
Nov 15 - Nov 16
Newly finished basement suite in Midlothian. Very clean and spacious.
A room with a fireplace, a mirror above it, and two leather chairs.

9. 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.
The price is CA $105
CA $196 total
includes taxes & fees
Nov 30 - Dec 1
Nest & Rest | Private Studio | Free Parking
A corner building with large windows and a black awning.

10. 402 Heart of the Arts in Downtown RVA near MCV VCU Convention Center

402 Heart of the Arts in Downtown RVA near MCV VCU Convention Center
Downtown Richmond
9.4 out of 10, Exceptional, (19 reviews)
"The building is right on a bus line, and was an easy to walk to various locations in the city as well as lots of restaurants."
United States
Jeffrey O.
The price is CA $104
CA $235 total
includes taxes & fees
Nov 9 - Nov 10
402 Heart of the Arts in Downtown RVA near MCV VCU Convention Center
A corner building with large windows and a black awning.

11. 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, (27 reviews)
"Great location, reasonable rates for the area, friendly helpful staff. Would stay here again."
United States
George L.
The price is CA $103
CA $234 total
includes taxes & fees
Nov 9 - Nov 10
Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
A modern kitchen with a central island, a dining area with a sofa and coffee table, and large windows offering a view.

12. 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, (93 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 $104
CA $235 total
includes taxes & fees
Nov 9 - Nov 10
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

13. 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 BirdHouse is such a comfortable place. We loved the uniqueness and the little touches that mean alot on the road. We hope to stay again sometime."
United States
paula S.
The price is CA $141
CA $280 total
includes taxes & fees
Nov 25 - Nov 26
The Birdhouse - Cozy Cottage Retreat in Richmond
A bedroom with a bed, a TV, and built-in shelving with decorative items.

14. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (25 reviews)
"Would stay again!"
United States
Amir D.
The price is CA $92
CA $156 total
includes taxes & fees
Nov 9 - Nov 10
Magnolias, a chill out place.
A room with a large window overlooking a cityscape.

15. Cozy studio apartment in tranquil Richmond with heat and gym access

Cozy studio apartment in tranquil Richmond with heat and gym access
Downtown Richmond
8.8 out of 10, Excellent, (9 reviews)
"Clean environment. Great views. Very little parking flexibility but an enjoyable walk."
United States
Cailyn
The price is CA $83
CA $114 total
includes taxes & fees
Nov 23 - Nov 24
Cozy studio apartment in tranquil Richmond with heat and gym access
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.

16. 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 traveller
The price is CA $65
CA $86 total
includes taxes & fees
Nov 9 - Nov 10
2 Full Beds|Non-Smoking
A hotel room with two beds, a window with a view of parked cars, a wooden headboard, and a framed picture on the wall.

17. 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 traveller
The price is CA $65
CA $86 total
includes taxes & fees
Nov 9 - Nov 10
2 Full Bed|Smoking|Petersburg VA
A gray sectional sofa with patterned cushions, a white door, decorative wall art, a window with blinds, and a small table with a lamp.

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

The Fan Comfort Stay near VCU Free Parking Fenced Yard
Fan District
9.6 out of 10, Exceptional, (32 reviews)
"Very convenient location, and great communication!"
United States
Katelyn F.
The price is CA $147
CA $269 total
includes taxes & fees
Nov 10 - Nov 11
The Fan Comfort Stay near VCU Free Parking Fenced Yard
A rural landscape with a pond, grassy fields, and trees under a cloudy sky.

19. 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 $159
CA $359 total
includes taxes & fees
Nov 11 - Nov 12
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A high-ceilinged interior with skylights and built-in shelving.

20. 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, (61 reviews)
"Great stay."
United States
Brian D.
Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
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

A residential building with a basketball court in front.
Residence Inn Marriott Chester

Residence Inn Marriott Chester

Residence Inn Marriott Chester
Chester

8/10 Good

Everything was fine. Very standard three star hotel. The continental breakfast was good. Well displayed. Coffee very good.
Canada
ZLATKO
Reviewed January 2, 2023
Residence Inn Marriott Chester

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 $65 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?

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.