Chester Vacation Rentals

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Our top choices for Chester vacation rentals

Houseboat in Richmond

Cookie B
3.0 star property
9.6 out of 10, Exceptional, (7)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
$164 nightly
The price is $187
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cookie B
9.6 out of 10, Exceptional, (113)
"2nd time staying at this property and definitely won’t be the last! Amazing location and great host."
United States
Alexis S.
$185 nightly
The price is $211
Dec 23 - Dec 24
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
10.0 out of 10, Exceptional, (10)
"House was amazing and host was very kind and helpful"
United States
Aaron R.
$143 nightly
The price is $154
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming 2-bedroom home, with lake access, in the Richmond metro area.

Houseboat in Richmond

MV GiaMaria
3.5 star property
9.2 out of 10, Wonderful, (16)
"We liked the coziness of the boat, the views of the river, the surrounding areas were beautiful. The only negative thing we could say was that due to the ran/wind the boat creaked and it made it hard to sleep for one of our nights."
United States
warren
$155 nightly
The price is $177
Jan 6 - Jan 7, 2026
Total with taxes and fees
MV GiaMaria
9.4 out of 10, Exceptional, (228)
"Beautiful setting and comfortable accommodations. "
United States
deirdre b.
$185 nightly
The price is $211
Dec 23 - Dec 24
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
2.0 star property
10.0 out of 10, Exceptional, (1)
"Check-in was simple and the space was perfect for my family."
United States
Eric B.
$186 nightly
The price is $212
Jan 5 - Jan 6, 2026
Total with taxes and fees
Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard
10.0 out of 10, Exceptional, (4)
"Amazing Stay. Very helpful & has everything you need . We will be coming back soon . Thank You James ! "
United Kingdom
Travis K.
$380 nightly
The price is $407
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres

Apartment in Church Hill

Historic Haven in Church Hill
10.0 out of 10, Exceptional, (46)
"Great place, great location!"
United States
Janet F.
$145 nightly
The price is $166
Dec 23 - Dec 24
Total with taxes and fees
Historic Haven in Church Hill
10.0 out of 10, Exceptional, (3)
"Had a great stay while fishing the james river. "
United States
Travis D.
$120 nightly
The price is $138
Jan 7 - Jan 8, 2026
Total with taxes and fees
Charming 1-bedroom apartment in Mechanicsville

Apartment in Richmond

Magnolias, a chill out place.
9.4 out of 10, Exceptional, (20)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
$102 nightly
The price is $117
Jan 5 - Jan 6, 2026
Total with taxes and fees
Magnolias, a chill out place.

Vacation Home in Midlothian

Private bedroom and bath!
10.0 out of 10, Exceptional, (1)
"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.
$202 nightly
The price is $233
Dec 23 - Dec 24
Total with taxes and fees
Private bedroom and bath!
9.6 out of 10, Exceptional, (28)
"Absolutely lovely and so convenient! We walked everywhere and didn’t take our cars out once. We shopped, ate at cute restaurants, wandered and visited the Virginia Museum of Fine Art, all on foot!"
United States
Melanie
$129 nightly
The price is $144
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy studio in FAN/museums /free parking
10.0 out of 10, Exceptional, (12)
"Hasan was such a wonderful host! Everything was simple and easy! He communicated all the things we would need ahead of time and the property is lovely! I can’t wait to come back!"
United States
Isabella c.
$230 nightly
The price is $262
Dec 23 - Dec 24
Total with taxes and fees
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
10.0 out of 10, Exceptional, (1)
"Our large family group enjoyed our stay here. The house is well-appointed and large. Everyone loved having their own bathrooms. Everything was clean and new condition. Just some minor things that were not deal-breakers for us. When I polled my family we pretty much all wished we had brought our own pillows. Parking is tight and awkward when neighbors are also parked, but at least there are reserved spots in a busy neighborhood. There are noise machines for each bed which is nice, but perhaps...
United States
Meg T.
$482 nightly
The price is $550
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern 5 Bedroom City Retreat + Walkable + Private Baths + Large Groups

Vacation Home in Northern Barton Heights

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
9.2 out of 10, Wonderful, (10)
"Loved it. Plenty of room for grandkids, their parents & I to have fun."
United States
Jane B.
$384 nightly
The price is $439
Jan 7 - Jan 8, 2026
Total with taxes and fees
Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
10.0 out of 10, Exceptional, (4)
"Such a fun place to stay! Room is nicely decorated. Easy check in/check out. Never stayed in this part of RVA before. We will definitely stay here again!"
United States
Teresa M.
$180 nightly
The price is $206
Dec 29 - Dec 30
Total with taxes and fees
Colorful private guesthouse in charming Richmond with Parking

Apartment in Church Hill

The Studio@ Eanes Drug
10.0 out of 10, Exceptional, (54)
"Great property! Perfect for what we needed!"
United States
Rob P.
$135 nightly
The price is $154
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Studio@ Eanes Drug

Apartment in Northern Barton Heights

Sunny, Spacious Suite Green & Shaded Backyard
10.0 out of 10, Exceptional, (2)
"The house was just as described. Very clean and very comfortable. The owner is easy to communicate with. "
United States
Kerri L.
$210 nightly
The price is $240
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sunny, Spacious Suite Green & Shaded Backyard
10.0 out of 10, Exceptional, (7)
"Everything was great about this verbo - the location, instructions, communications with owner. Highly recommend!"
United States
Carol M.
$310 nightly
The price is $354
Dec 29 - Dec 30
Total with taxes and fees
2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi
3.0 star property
$272 nightly
The price is $311
Jan 7 - Jan 8, 2026
Total with taxes and fees
Richmond Home w/ Fire Pit - 12 Mi to Downtown
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

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 $144 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.

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?

Cozy walkable downtown retreat, 3 minutes to VCU: This vacation home rental outside of Chester is located in the city center and offers a selection of games, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chester?

With 7 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. Appomattox River and Parker's Battery 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.