Chester Vacation Rentals from $183: Search Short-Term Rentals

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Our top choices for Chester vacation rentals

1. Game Room + Yard: Updated House in Chester!

Chester

$304 nightly

Aug 9 - Aug 10

Total with taxes and fees

2. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

Richmond

FARYL H.

$186 nightly

Aug 9 - Aug 10

Total with taxes and fees

3. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

Richmond

norma W.

$188 nightly

Aug 12 - Aug 13

Total with taxes and fees

3 bedrooms, desk, iron/ironing board, WiFi (free)

4. Family friendly! Recline at Timberline..

South chesterfield

James W.

$296 nightly

Aug 13 - Aug 14

Total with taxes and fees

5. Cookie B

Richmond

Reshelle

$256 nightly

Aug 7 - Aug 8

Total with taxes and fees

6. MV GiaMaria

Richmond

Jane

$243 nightly

Aug 23 - Aug 24

Total with taxes and fees

7. Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Chesterfield

G H.

$215 nightly

Aug 7 - Aug 8

Total with taxes and fees

8. The Birdhouse - Cozy Cottage Retreat in Richmond

Swansboro West

paula S.

$205 nightly

Aug 12 - Aug 13

Total with taxes and fees

9. Newly finished basement suite in Midlothian. Very clean and spacious.

Midlothian

Jeannie C.

$211 nightly

Sep 2 - Sep 3

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

10. The Studio@ Eanes Drug-Heart of the Historic District

Church Hill

Gary P.

$160 nightly

Aug 11 - Aug 12

Total with taxes and fees

11. Historic Haven in Church Hill in The Heart of the Historic District

Church Hill

Danelle B.

$170 nightly

Aug 11 - Aug 12

Total with taxes and fees

12. Lovely 2 Bedroom in the Heart of The Fan

Fan District

Ryanne T.

$332 nightly

Aug 10 - Aug 11

Total with taxes and fees

1 bedroom, in-room safe, WiFi (free), bed sheets

13. Magnolias, a chill out place.

Richmond

Amir D.

$129 nightly

Aug 29 - Aug 30

Total with taxes and fees

14. Cozy 2-bedroom apartment in beautiful Fan District

Fan District

Dorothy A S.

$244 nightly

Sep 1 - Sep 2

Total with taxes and fees

15. Luxe King Bd W Resort Amenities

Moseley

Lisa H.

$176 nightly

Aug 9 - Aug 10

Total with taxes and fees

16. Sunny, Spacious Suite Green & Shaded Backyard

Northern Barton Heights

Kerri L.

17. Colorful private guesthouse in charming Richmond with Parking

Northern Barton Heights

Jim H.

$192 nightly

Aug 10 - Aug 11

Total with taxes and fees

1 bedroom, desk, iron/ironing board, WiFi

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

Virginia Union

Michelle S.

$218 nightly

Aug 19 - Aug 20

Total with taxes and fees

19. Oaks Retreat Carytown House: Family & Pet Friendly

Randolph

Thomas C.

$252 nightly

Aug 10 - Aug 11

Total with taxes and fees

20. Private Garden Home w/ Large Fenced Yard + Gazebo

Broad Rock

"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...

Stacie C.

$321 nightly

Aug 31 - Sep 1

Total with taxes and fees

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Top Chester Hotel Reviews

Graduate by Hilton Richmond

10/10 Excellent

"Hotel was very clean, comfortable, and had a great location! Valet parking got a bit backed up at times, especially around check-in time on a Friday. Once checked in, there was a website link you could use to order the car in advance. When I did that it was always ready when I requested it."

The Jefferson Hotel

10/10 Excellent

"The Jefferson Hotel is one of a vanishing breed of grand historic hotels that still provide the kind of hotel experience that was already becoming rare 50 years ago. The staff are friendly and attentive, the rooms are extremely well appointed, the public spaces of the hotel are spectacular, and the restaurant is one of the best in Richmond. The hotel's only real drawback isn't its fault: the area of downtown Richmond that the Jefferson used to anchor has seriously deteriorated. Even though an effort was clearly made to try to revive Broad Street near the hotel, it's still pretty sketchy. As a result, there isn't really much of interest close to the hotel other than VCU and the Virginia Museum of Contemporary Art. That means that going out from the hotel -- to find other restaurants, see the sights, or hit the usual tourist destinations -- pretty much requires a car."

The Commonwealth

8/10 Good

"The Commonwealth is our "go to" hotel when we stay in Richmond, Virginia, primarily because the rooms are huge and a great value, and the staff is friendly, helpful and determined. I do have to mention, though, that I would hope the hotel would hire more staff members. It appears that the staff on hand are expected to serve many roles, which causes the service to lag. For instance, when we checked in this last time, there was no one at the reception desk and the housekeeping supervisor partially checked us in after a long wait. I've also noticed the last couple times that we stayed that the restaurant is often lacking advertised entries or beverages. It would be great if that area was well stocked with food items, beverage choices and enough inventory to serve all guests. Still will stay at The Commonwealth though."

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 $183 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.

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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 Henricus Historical Park are a couple of great spots to enjoy the outdoors. Dutch Gap Conservation Area 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.

Chester Vacation Rentals

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Check prices for these dates

Our top choices for Chester vacation rentals

1. Game Room + Yard: Updated House in Chester!

2. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

3. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

4. Family friendly! Recline at Timberline..

5. Cookie B

6. MV GiaMaria

7. Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

8. The Birdhouse - Cozy Cottage Retreat in Richmond

9. Newly finished basement suite in Midlothian. Very clean and spacious.

10. The Studio@ Eanes Drug-Heart of the Historic District

11. Historic Haven in Church Hill in The Heart of the Historic District

12. Lovely 2 Bedroom in the Heart of The Fan

13. Magnolias, a chill out place.

14. Cozy 2-bedroom apartment in beautiful Fan District

15. Luxe King Bd W Resort Amenities

16. Sunny, Spacious Suite Green & Shaded Backyard

17. Colorful private guesthouse in charming Richmond with Parking

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

19. Oaks Retreat Carytown House: Family & Pet Friendly

20. Private Garden Home w/ Large Fenced Yard + Gazebo

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Graduate by Hilton Richmond

Find out more about Chester

Explore a world of travel with Expedia

Frequently asked questions

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