Chester Vacation Rentals

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Vacation Rentals in Chester

Pool
Luxury Apt in Diamond District - Scott’s Addition
Luxury Apt in Diamond District - Scott’s Addition
3.4 out of 10, (3)
"The property was in a great location to the places we needed to be. We were disappointed that there was 1 bath towel, no wash clothes and two hand towels for our use. The listing stated two bedrooms, it was one bedroom with a pull out sofa however stated the unit slept 5. There were no sharp knives in the unit. I normally carry a ton of items and have gotten out of the habit as these are things that should be standard items in the units. "
United States
Carol R.
Luxury Apt in Diamond District - Scott’s Addition
Fridge, microwave, oven, stovetop
Historic Haven in Church Hill
Historic Haven in Church Hill
10.0 out of 10, Exceptional, (39)
"Amazing property within walking distance of incredible restaurants and bars"
United States
Carly J.
$150 nightly
The price is $192
Nov 9 - Nov 10
Total with taxes and fees
Historic Haven in Church Hill
Fridge, microwave, oven, stovetop
The Studio@ Eanes Drug
The Studio@ Eanes Drug
10.0 out of 10, Exceptional, (46)
"Amazing, awesome and convenient place to stay in Richmond. "
United States
Richard W.
$140 nightly
The price is $179
Nov 4 - Nov 5
Total with taxes and fees
The Studio@ Eanes Drug
View from property
MV GiaMaria
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
$189 nightly
The price is $215
Nov 4 - Nov 5
Total with taxes and fees
MV GiaMaria
Interior
Landing Apartments near Virginia Union University
Landing Apartments near Virginia Union University
3.5 star property
8.8 out of 10, Excellent, (18)
"This was a clean, well-equipped and comfortable apartment. The location is good but does require a car to explore the city and pick up groceries. Parking was easy and free. The balcony was a nice place to sit as the temperature got warmer. Air conditioning was very effective. Would stay again."
United Kingdom
Frances
Landing Apartments near Virginia Union University
Fridge, microwave, oven, stovetop
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Stylish retreat in charming Richmond with Private Sauna and other modern touches
9.8 out of 10, Exceptional, (19)
"We had a nice stay. The beds were comfortable and the inside of the property is good. "
United States
Michael W.
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Smart TV, fireplace, computer monitors
Charming 1-bedroom suite with WiFi and AC in Bon Air
Charming 1-bedroom suite with WiFi and AC in Bon Air
10.0 out of 10, Exceptional, (7)
"It was a nice stay the host was prompt and answered any questions or concerns right away, she was very polite and helpful to me and family "
United States
Jessica H.
$176 nightly
The price is $211
Nov 4 - Nov 5
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
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
9.4 out of 10, Exceptional, (224)
"Very peaceful. Lovely views"
United States
george j.
$185 nightly
The price is $222
Nov 4 - Nov 5
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Outdoor dining
The Grace Escape
The Grace Escape
10.0 out of 10, Exceptional, (30)
"We enjoyed our stay here. House was clean and it had everything we needed."
United States
Kim M.
The Grace Escape
Fridge, microwave, oven, stovetop
Downtown Living in Historic Richmond Loft
Downtown Living in Historic Richmond Loft
8.2 out of 10, Very Good, (62)
"We were in Ohio for our granddaughters graduation. It was a quick trip up but we wished we could have stayed longer. The house was exactly what we needed! It is a beautiful property that is beautifully appointed. It was exactly what we needed!!"
United States
Wanda B.
$288 nightly
The price is $312
Nov 13 - Nov 14
Total with taxes and fees
Downtown Living in Historic Richmond Loft
Microwave, oven, stovetop, dishwasher
Luxe Modern Escape in Downtown Richmond - 2b2b
Luxe Modern Escape in Downtown Richmond - 2b2b
6.8 out of 10, (3)
"Check in was tough. We were led to the wrong apartment. The property owner did get back to me in less than 5 minutes, which was great! She said she will fix this issue. I would let others know that the property has a ton of stairs. Probably 20 once you get into the building and 10 inside the apartment. It’s beautiful wood flooring. But very slippery for elderly and dogs. I would also note that parking at a nearby lot was 25 a day. So for us- it costs 100 in parking (2 cars). This might be on the...
United States
serena b.
$372 nightly
The price is $476
Nov 10 - Nov 11
Total with taxes and fees
Luxe Modern Escape in Downtown Richmond - 2b2b
Fridge, microwave, oven, stovetop
Midlothian 3 Bedroom getaway for up to 8 guests!
Midlothian 3 Bedroom getaway for up to 8 guests!
9.4 out of 10, Exceptional, (16)
"Very cleanly stay along with amenities within walking distance."
United States
Jason L.
$451 nightly
The price is $541
Nov 10 - Nov 11
Total with taxes and fees
Midlothian 3 Bedroom getaway for up to 8 guests!
Fridge, microwave, oven, stovetop
Spacious and Cozy Oasis on Monument Avenue
Spacious and Cozy Oasis on Monument Avenue
10.0 out of 10, Exceptional, (24)
"Property was so relaxing after a day exploring Richmond. Our host was great and very responsive. Hope we can stay again when we can enjoy the pool."
United States
Jackie T.
Spacious and Cozy Oasis on Monument Avenue
Pool
VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck
VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck
10.0 out of 10, Exceptional, (124)
"Amazing location. Would stay again"
United States
kerry p.
$423 nightly
The price is $541
Nov 13 - Nov 14
Total with taxes and fees
VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck
Fridge, microwave, oven, stovetop
Oaks Retreat Carytown House: Family & Pet Friendly
Oaks Retreat Carytown House: Family & Pet Friendly
9.6 out of 10, Exceptional, (10)
"Had a very nice stay at this location. Plenty of room and parking. Slept 8 easy. Good for a group weekend in Richmond."
United States
Nathan J.
$227 nightly
The price is $251
Nov 5 - Nov 6
Total with taxes and fees
Oaks Retreat Carytown House: Family & Pet Friendly
Dining
Cozy Cabin @James River; Live/Work/Play Experience
Cozy Cabin @James River; Live/Work/Play Experience
10.0 out of 10, Exceptional, (12)
"Property is great & well managed "
United States
Sterling C.
Cozy Cabin @James River; Live/Work/Play Experience
Terrace/patio
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
9.8 out of 10, Exceptional, (128)
"Everything you need for a stay in Richmond, especially if you have family at VCU. "
United States
Lisa F.
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
Fridge, microwave, oven, stovetop
Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Living in Richmond's Amazing Shockoe Bottom
8.6 out of 10, Excellent, (30)
"Loved it!"
United States
Christina B.
$221 nightly
The price is $239
Nov 4 - Nov 5
Total with taxes and fees
Downtown Living in Richmond's Amazing Shockoe Bottom
Fridge, microwave, oven, stovetop
Spacious Carytown Home: 6BR, Free Parking!
Spacious Carytown Home: 6BR, Free Parking!
2.0 star property
10.0 out of 10, Exceptional, (6)
"Don’t just look book lol, we enjoyed our stay will stay again"
United States
mack 1.
$486 nightly
The price is $539
Nov 5 - Nov 6
Total with taxes and fees
Spacious Carytown Home: 6BR, Free Parking!
Interior
NEW! Upscale Escape | Game Room & Spa-Like Baths
NEW! Upscale Escape | Game Room & Spa-Like Baths
9.0 out of 10, Wonderful, (7)
"The house was great and clean on the surface. It was a cute home with a mixture of modern and old school feel. There were minor issues, however not too serious. My family was comfortable and enjoyed their stay, most especially the foosball table, air hockey, and chess/checkers games. I found opened bottles of water in the sunroom and in one of the bedrooms, a sock, and a flashlight noticeably under the nightstand. Although we didn’t stay the whole way due to weather issues (caused a power...
United States
Randy-Tawnee E.
NEW! Upscale Escape | Game Room & Spa-Like Baths
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

Studio 6 Richmond Airport

Studio 6 Richmond Airport

10/10 Excellent
"Location location "
Adrian 2-night trip
Posted 2 days ago
Studio 6 Richmond Airport

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 $179 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?

Stylish retreat in charming Richmond with Private Sauna and other modern touches: 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. 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 Appomattox River are a couple of great spots to enjoy the outdoors. Henricus Historical Park 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.