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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Chester vacation rentals

Exterior

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Lanexa
10.0 out of 10, Exceptional, (7 reviews)
"First and foremost, the property was excellent! The host, Michael was extremely welcoming and kind. The property is in top condition with new everything! The seclusion and lakefront location was to die for. Highly recommend this property as we will be back! "
United States
Kelly B.
$669 nightly
The price is $723
Jul 31 - Aug 1
Total with taxes and fees
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
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.
$603 nightly
The price is $647
Jul 1 - Jul 2
Total with taxes and fees
Red Juniper Retreat
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
$398 nightly
The price is $447
Jul 7 - Jul 8
Total with taxes and fees
Luxury Stay! 10 min away from Fort Lee.
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, (120 reviews)
"Very nice stay! Awesome host and quiet neighborhood! Thank you!"
United States
Wes E.
$186 nightly
The price is $213
Jul 1 - Jul 2
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Outdoor dining

A Clean, Safe, House full of steel balls & vintage game consoles

A Clean, Safe, House full of steel balls & vintage game consoles
Dumbarton
9.8 out of 10, Exceptional, (29 reviews)
"Always a great stay at Robert’s place. This was our second time staying there. Very clean and safe. Would definitely stay there again."
United States
James K.
$567 nightly
The price is $647
Jul 5 - Jul 6
Total with taxes and fees
A Clean, Safe, House full of steel balls & vintage game consoles
Terrace/patio

Private Garden Home w/ Large Fenced Yard + Gazebo

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay here for two nights! The beds were extremely comfortable and it was quiet and peaceful sleeping there both nights. We enjoyed the backyard very much - both our pets and kids. My son thought the gazebo with twinkle lights out back was so magical. :) We appreciate the cleanliness of the place and would only have appreciated a little space with maybe kids’ books, puzzles, or blocks or something. My young kiddos go crazy for those things when we stay at vacation rentals and it...
United States
Stacie C.
$293 nightly
The price is $335
Jul 1 - Jul 2
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
Fridge, microwave, oven, stovetop

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, (69 reviews)
"Nice stay"
United States
Danelle B.
$165 nightly
The price is $189
Jul 5 - Jul 6
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
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
8.0 out of 10, Very Good, (1 review)
$333 nightly
The price is $381
Jul 1 - Jul 2
Total with taxes and fees
Relax in beautiful second floor apartment with balcony & private fenced yard.
Fridge, microwave, oven, stovetop

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, (83 reviews)
"Great option and neighborhood- enjoyed the stay"
United States
Gary P.
$160 nightly
The price is $183
Jul 1 - Jul 2
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
Private kitchen

RVA Retreat Sauna Relaxing Home Fenced Yard

RVA Retreat Sauna Relaxing Home Fenced Yard
Church Hill North
$429 nightly
The price is $490
Jul 5 - Jul 6
Total with taxes and fees
RVA Retreat Sauna Relaxing Home Fenced Yard
Exterior detail

Cozy 3 BdRm Cape Cottage in Green Park, RVA - 10 minutes 2 Downtown

Cozy 3 BdRm Cape Cottage in Green Park, RVA - 10 minutes 2 Downtown
Green Park
Cozy 3 BdRm Cape Cottage in Green Park, RVA - 10 minutes 2 Downtown
1 bedroom, free WiFi, bed sheets

The Farmhouse Retreat

The Farmhouse Retreat
Mechanicsville
10.0 out of 10, Exceptional, (4 reviews)
"Had a great stay while fishing the james river. "
United States
Travis D.
$139 nightly
The price is $160
Jul 6 - Jul 7
Total with taxes and fees
The Farmhouse Retreat
Living area

The New Amsterdam Nook 2 Bed - 1 Bath - Full Kitchen - Pool - AC

The New Amsterdam Nook 2 Bed - 1 Bath - Full Kitchen - Pool - AC
Mechanicsville
$128 nightly
The price is $147
Jul 21 - Jul 22
Total with taxes and fees
The New Amsterdam Nook 2 Bed - 1 Bath - Full Kitchen - Pool - AC
Interior

Carytown Gem: Family-Friendly Apartment with Yard

Carytown Gem: Family-Friendly Apartment with Yard
Carytown
9.8 out of 10, Exceptional, (76 reviews)
"Great location!!"
United States
Elizabeth S.
$203 nightly
The price is $223
Jul 5 - Jul 6
Total with taxes and fees
Carytown Gem: Family-Friendly Apartment with Yard
Interior

3-bedroom house. Minutes away from major hospitals. Close to RIR, VCU, VUU, VSU.

3-bedroom house. Minutes away from major hospitals. Close to RIR, VCU, VUU, VSU.
Richmond
9.2 out of 10, Wonderful, (7 reviews)
"It was a nice, clean place to stay. "
United States
Lauri O.
$328 nightly
The price is $375
Jul 6 - Jul 7
Total with taxes and fees
3-bedroom house. Minutes away from major hospitals. Close to RIR, VCU, VUU, VSU.
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, (239 reviews)
"The houseboat was exactly as described and met as well as exceeding my expectations. Very peaceful, overlooking the river. The bed was comfortable and I love every minute of our stay, just wish it had been longer. We met Capt. Ron on our last night. He is a very nice man and loved talking with him. I hope to return in the future. Barbara and Ben"
United States
Barbara
$186 nightly
The price is $213
Jul 1 - Jul 2
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Interior

Charming Getaway in the Heart of RVA-No Cleaning Fee

Charming Getaway in the Heart of RVA-No Cleaning Fee
Southern Barton Heights
10.0 out of 10, Exceptional, (7 reviews)
"House was perfect. "
United States
Sovi T.
$513 nightly
The price is $586
Jul 1 - Jul 2
Total with taxes and fees
Charming Getaway in the Heart of RVA-No Cleaning Fee
Terrace/patio

Relaxing & Quiet Retreat Fully Fenced Backyard

Relaxing & Quiet Retreat Fully Fenced Backyard
Bellevue
$434 nightly
The price is $496
Jul 1 - Jul 2
Total with taxes and fees
Relaxing & Quiet Retreat Fully Fenced Backyard
2 bedrooms, WiFi, bed sheets

Earth & Ember -Cottage House Retreat!

Earth & Ember -Cottage House Retreat!
North Highland Park
$257 nightly
The price is $294
Jul 5 - Jul 6
Total with taxes and fees
Earth & Ember -Cottage House Retreat!
Exterior detail

Charming Fan District Getaway

Charming Fan District Getaway
Fan District
9.8 out of 10, Exceptional, (34 reviews)
"Lovely stay at a historic home. Super appreciative of these very attentive owners. Excellent location and was able to spend time with family. "
United States
Brandy M.
$499 nightly
The price is $570
Jul 20 - Jul 21
Total with taxes and fees
Charming Fan District Getaway
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

Holiday Inn Express Chester by IHG

Holiday Inn Express Chester by IHG

10/10 Excellent
"Very clean and smelled great. Everyone was friendly"
Victor 2-night trip
Posted 10 hours ago
Holiday Inn Express Chester by IHG

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 $138 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?

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