Chester Vacation Rentals

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Our top choices for Chester vacation rentals

MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
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

Cookie B

Cookie B
3.0 star property
Richmond
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

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
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.

Studio Nest/2Queen beds/2TVs museums/free parking

Studio Nest/2Queen beds/2TVs museums/free parking
Fan District
10.0 out of 10, Exceptional, (52)
"Everything was great!"
United States
Ingrid R.
$133 nightly
The price is $147
Jan 7 - Jan 8, 2026
Total with taxes and fees
Studio Nest/2Queen beds/2TVs museums/free parking

Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
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
$104 nightly
The price is $119
Jan 12 - Jan 13, 2026
Total with taxes and fees
Magnolias, a chill out place.

Charming 1-bedroom apartment in Mechanicsville

Charming 1-bedroom apartment in Mechanicsville
Mechanicsville
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

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (31)
"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.
$208 nightly
The price is $222
Jan 1 - Jan 2, 2026
Total with taxes and fees
Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Historic Richmond Loft

Downtown Living in Historic Richmond Loft
Downtown Richmond
8.2 out of 10, Very Good, (64)
"Clean room and close to restaurants and bars"
United States
Jason P.
$252 nightly
The price is $269
Jan 4 - Jan 5, 2026
Total with taxes and fees
Downtown Living in Historic Richmond Loft

Carytown Gem: Family-Friendly Apartment with Yard

Carytown Gem: Family-Friendly Apartment with Yard
Carytown
9.8 out of 10, Exceptional, (66)
"Vibrant neighborhood "
United States
Timoteo S.
$197 nightly
The price is $216
Jan 5 - Jan 6, 2026
Total with taxes and fees
Carytown Gem: Family-Friendly Apartment with Yard

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, (228)
"Beautiful setting and comfortable accommodations. "
United States
deirdre b.
$185 nightly
The price is $211
Jan 6 - Jan 7, 2026
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

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, (113)
"2nd time staying at this property and definitely won’t be the last! Amazing location and great host."
United States
Alexis S.
$186 nightly
The price is $213
Dec 31 - Jan 1, 2026
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
9.8 out of 10, Exceptional, (55)
"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

The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres

The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres
Charles City County
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.
$373 nightly
The price is $399
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres

Historic Haven in Church Hill

Historic Haven in Church Hill
Church Hill
10.0 out of 10, Exceptional, (46)
"Great place, great location!"
United States
Janet F.
$145 nightly
The price is $166
Jan 4 - Jan 5, 2026
Total with taxes and fees
Historic Haven in Church Hill

Modern, Lovely and Spacious Home

Modern, Lovely and Spacious Home
Downtown Richmond
9.8 out of 10, Exceptional, (29)
"Great little house in a convenient location. We would definitely stay here again next time we're in town "
United States
Allison B.
$439 nightly
The price is $502
Jan 2 - Jan 3, 2026
Total with taxes and fees
Modern, Lovely and Spacious Home

Private Guest house with Parking and Wi-Fi in a Central Location

Private Guest house with Parking and Wi-Fi in a Central Location
Virginia Union
10.0 out of 10, Exceptional, (4)
"A perfect VRBO: clean, tastefully decorated, great location, safe, comfortable bed, great communication, and an overall warm welcoming feel. I would love to stay in Amanda’s VRBO again when visiting Richmond."
United States
Sandra D.
$215 nightly
The price is $245
Jan 6 - Jan 7, 2026
Total with taxes and fees
Private Guest house with Parking and Wi-Fi in a Central Location

Casa Terra: Pet-Friendly Eco Oasis with Gazebo

Casa Terra: Pet-Friendly Eco Oasis with Gazebo
Broad Rock
10.0 out of 10, Exceptional, (1)
"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.
$262 nightly
The price is $300
Jan 5 - Jan 6, 2026
Total with taxes and fees
Casa Terra: Pet-Friendly Eco Oasis with Gazebo

Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond

Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
Fan District
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.
$233 nightly
The price is $266
Jan 4 - Jan 5, 2026
Total with taxes and fees
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond

Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard

Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard
2.0 star property
Malvern Gardens
10.0 out of 10, Exceptional, (2)
"Check-in was simple and the space was perfect for my family."
United States
Eric B.
$218 nightly
The price is $249
Jan 26 - Jan 27, 2026
Total with taxes and fees
Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard

Sunny, Spacious Suite Green & Shaded Backyard

Sunny, Spacious Suite Green & Shaded Backyard
Northern Barton Heights
10.0 out of 10, Exceptional, (3)
"Absolutely no issues during my brief stay with my host. I and my dog particularly enjoyed the backyard space. "
United States
Danielle A.
$206 nightly
The price is $235
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sunny, Spacious Suite Green & Shaded Backyard
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?

Great Location. Close to about everywhere .Can't beat the value. Check reviews!: This vacation home rental outside of Chester is located on a river and has a patio, a garden, and air-conditioning to put you at ease 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.