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

Q: What's the top vacation rental in Chester?

Fantastic 5-bedroom Luxury home in charming Richmond : This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chester vacation rentals

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

Chester

$430 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Chester

Akia S.

$439 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Richmond

FARYL H.

$188 nightly

Aug 16 - Aug 17

Total with taxes and fees

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

Richmond

norma W.

$189 nightly

Aug 23 - Aug 24

Total with taxes and fees

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

5. Family friendly! Recline at Timberline..

South chesterfield

James W.

6. Cookie B

Richmond

Reshelle

$263 nightly

Aug 15 - Aug 16

Total with taxes and fees

7. MV GiaMaria

Richmond

Jane

$243 nightly

Aug 23 - Aug 24

Total with taxes and fees

8. The Birdhouse - Cozy Cottage Retreat in Richmond

Swansboro West

Andrea

$204 nightly

Aug 18 - Aug 19

Total with taxes and fees

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

Chesterfield

G H.

$223 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

Midlothian

Jeannie C.

$198 nightly

Sep 7 - Sep 8

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Church Hill

Gary P.

$160 nightly

Aug 16 - Aug 17

Total with taxes and fees

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

Church Hill

Danelle B.

$171 nightly

Aug 16 - Aug 17

Total with taxes and fees

13. Carytown cozy nest private room Fenced Yard

Carytown

Bonnie W.

$124 nightly

Aug 16 - Aug 17

Total with taxes and fees

14. Lovely 2 Bedroom in the Heart of The Fan

Fan District

Nancy D.

$359 nightly

Aug 21 - Aug 22

Total with taxes and fees

15. Luxe King Bd W Resort Amenities

Moseley

Lisa H.

$178 nightly

Aug 16 - Aug 17

Total with taxes and fees

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

16. Magnolias, a chill out place.

Richmond

Amir D.

$105 nightly

Sep 13 - Sep 14

Total with taxes and fees

17. Private bedroom and bath!

Midlothian

Ridge W.

$205 nightly

Aug 15 - Aug 16

Total with taxes and fees

18. Qualla Park

Chesterfield County

Shannon W.

$434 nightly

Aug 23 - Aug 24

Total with taxes and fees

19. Cozy 2-bedroom apartment in beautiful Fan District

Fan District

Dorothy A S.

$245 nightly

Aug 30 - Aug 31

Total with taxes and fees

20. Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Richmond

Dillon D.

$308 nightly

Aug 24 - Aug 25

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chester Hotel Reviews

Best Western Plus Glen Allen Inn

10/10 Excellent

"Nice place to stay, good parking, great breakfast and clean room."

Linden Row Inn

8/10 Good

"Huge rooms! Character! And a cat! After staying at some bigger chain hotels, I thought it was time for something different - this inn is historic, has a great location right next to the library and around the corner from Perly's Delicatessen, and Annabelle is a friendly cat that even this dog lover could appreciate. There are some tradeoffs like older locks/keys and thinner walls, but to me this was a memorable stay and I even got an Edgar Allan Poe tote bag. Will definitely return when it's a bit cooler out and I can manage walking a bit further - check it out!"

Omni Richmond Hotel

10/10 Excellent

"Omni Hotel is top notch, this was our first time staying at an Omni Hotel and we loved it. It was clean, the staff was awesome, they provided us with great places to visit, and eat. And I cant say enough about the bed....it was the most comfortable bed we've slept in away from home. We've stayed at other brand properties but none compare to the service and quality at the Omni Richmond."

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.

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?

Fantastic 5-bedroom Luxury home in charming Richmond: This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Dutch Gap Conservation Area are a couple of great spots to enjoy the outdoors. Point of Rocks Park and Appomattox River 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

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chester vacation rentals

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

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

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

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

5. Family friendly! Recline at Timberline..

6. Cookie B

7. MV GiaMaria

8. The Birdhouse - Cozy Cottage Retreat in Richmond

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

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

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

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

13. Carytown cozy nest private room Fenced Yard

14. Lovely 2 Bedroom in the Heart of The Fan

15. Luxe King Bd W Resort Amenities

16. Magnolias, a chill out place.

17. Private bedroom and bath!

18. Qualla Park

19. Cozy 2-bedroom apartment in beautiful Fan District

20. Downtown Living in Richmond's Amazing Shockoe Bottom

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Best Western Plus Glen Allen Inn

Find out more about Chester

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app