Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Chester vacation rentals

Living area

The SageBrush Cottage

The SageBrush Cottage
North Highland Park
The price is ￥20,068
￥50,600 total
includes taxes & fees
Jun 8 - Jun 9
The SageBrush Cottage
Lobby

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, (117 reviews)
"Very nice stay! Awesome host and quiet neighborhood! Thank you!"
United States
Wes E.
The price is ￥18,316
￥33,670 total
includes taxes & fees
Jun 1 - Jun 2
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Beach nearby

Charming 2-bedroom home, with lake access, in the Richmond metro area.

Charming 2-bedroom home, with lake access, in the Richmond metro area.
Quinton
9.8 out of 10, Exceptional, (17 reviews)
"If fishing is your thing, this place seems just the place for you. It's has guest passes to the lake. The bed was very comfortable. IMO, the kitchen needs better cookware."
United States
Kimberly
The price is ￥25,165
￥30,618 total
includes taxes & fees
Jun 7 - Jun 8
Charming 2-bedroom home, with lake access, in the Richmond metro area.
Property grounds

Hidden Heaven lake house. Quiet private cottage on 1 acre

Hidden Heaven lake house. Quiet private cottage on 1 acre
Lanexa
10.0 out of 10, Exceptional, (48 reviews)
"Joyce and Eric are fantastic hosts. We had a nice relaxing time. It was close to all the historical sites we wanted to see."
United States
Steve R.
The price is ￥35,692
￥69,680 total
includes taxes & fees
Jun 1 - Jun 2
Hidden Heaven lake house. Quiet private cottage on 1 acre
Marina

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, (236 reviews)
"Beautiful setting and comfortable accommodations. "
United States
deirdre b.
The price is ￥18,316
￥33,670 total
includes taxes & fees
Jun 1 - Jun 2
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Fridge, microwave, oven, stovetop

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
10.0 out of 10, Exceptional, (78 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is ￥22,298
￥29,121 total
includes taxes & fees
Jun 1 - Jun 2
The Studio@ Eanes Drug
Fridge, microwave, oven, stovetop

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, (17 reviews)
"The home was very clean and very comfortable. Communication was excellent. We would definitely stay here again!"
United States
CHRIS
The price is ￥23,652
￥66,091 total
includes taxes & fees
Jun 1 - Jun 2
Luxury Stay! 10 min away from Fort Lee.
Exterior

Red Juniper Retreat

Red Juniper Retreat
New Kent
10.0 out of 10, Exceptional, (26 reviews)
"The house is wonderful, and the owners are amazing! Absolutely love staying here. "
United States
Samantha B.
The price is ￥49,167
￥102,975 total
includes taxes & fees
Jun 1 - Jun 2
Red Juniper Retreat
Interior

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (34 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.
The price is ￥18,228
￥51,582 total
includes taxes & fees
Jun 1 - Jun 2
Downtown Living in Richmond's Amazing Shockoe Bottom
1 bedroom, in-room safe, free WiFi, bed sheets

Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (23 reviews)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
The price is ￥11,324
￥20,221 total
includes taxes & fees
Jun 3 - Jun 4
Magnolias, a chill out place.
Fridge, microwave, oven, stovetop

Historic Haven in Church Hill

Historic Haven in Church Hill
Church Hill
10.0 out of 10, Exceptional, (67 reviews)
"Amazing stay, every detail was considered. Beautiful home, walkable neighborhood, everything was perfect!"
United States
Becky S.
The price is ￥23,891
￥30,943 total
includes taxes & fees
Jun 15 - Jun 16
Historic Haven in Church Hill
Smart TV, fireplace

The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (1 review)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
The price is ￥14,298
￥31,407 total
includes taxes & fees
Jun 4 - Jun 5
The Birdhouse - Cozy Cottage Retreat in Richmond
Dining

Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (28 reviews)
"Everything was smooth and as promised. We recommend this spot!"
United States
Stefin P.
The price is ￥11,945
￥23,070 total
includes taxes & fees
Jun 3 - Jun 4
Carytown cozy nest private room Fenced Yard
TV

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, (84 reviews)
"Easy check in and a pleasant quick stay "
United States
Megan M.
The price is ￥18,228
￥56,349 total
includes taxes & fees
Jun 1 - Jun 2
Lovely 2 Bedroom in the Heart of The Fan
Interior

Tourist Home of Richmond 1-bedroom apartment - Church Hill North TH06

Tourist Home of Richmond 1-bedroom apartment - Church Hill North TH06
Woodville
The price is ￥19,112
￥38,588 total
includes taxes & fees
Jun 1 - Jun 2
Tourist Home of Richmond 1-bedroom apartment - Church Hill North TH06
Dining

Nest & Rest/Free Parking/Museum/City Access

Nest & Rest/Free Parking/Museum/City Access
Fan District
9.8 out of 10, Exceptional, (45 reviews)
"Everything was great! And great location!"
United States
Meg S.
The price is ￥11,627
￥23,338 total
includes taxes & fees
Jun 2 - Jun 3
Nest & Rest/Free Parking/Museum/City Access
Terrace/patio

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Northern Barton Heights
9.6 out of 10, Exceptional, (16 reviews)
"Great kitchen and comfy beds."
United States
Christina O.
The price is ￥17,042
￥64,070 total
includes taxes & fees
Jun 29 - Jun 30
Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Interior

Cozy Bon Air Guest Suite with Private Entrance

Cozy Bon Air Guest Suite with Private Entrance
Bon Air
The price is ￥12,423
￥25,091 total
includes taxes & fees
Jun 30 - Jul 1
Cozy Bon Air Guest Suite with Private Entrance
Interior

Carytown Gem: Family-Friendly Apartment with Yard

Carytown Gem: Family-Friendly Apartment with Yard
Carytown
9.8 out of 10, Exceptional, (75 reviews)
"Very clean, everything we needed, comfortable beds!!"
United States
Chris K.
The price is ￥16,564
￥34,980 total
includes taxes & fees
Jun 2 - Jun 3
Carytown Gem: Family-Friendly Apartment with Yard
Interior

Relax in beautiful second floor apartment with balcony & private fenced yard.

Relax in beautiful second floor apartment with balcony & private fenced yard.
Northern Barton Heights
The price is ￥27,872
￥60,427 total
includes taxes & fees
Jun 1 - Jun 2
Relax in beautiful second floor apartment with balcony & private 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

Graduate by Hilton Richmond

Graduate by Hilton Richmond

10/10 Excellent
"A wonderful hotel and pleasant staff!"
Jana 1-night trip
Posted 6 hours ago
Graduate by Hilton Richmond

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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?

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!: This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Parker's Battery Park are a couple of great spots to enjoy the outdoors. Henricus Historical Park 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.