Chester Holiday Rentals

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Holiday Rentals in Chester

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
The price is AU$303
includes taxes & fees
1 Dec - 2 Dec
Cookie B

Magnolias, a chill out place.

Richmond
9.4 out of 10, Exceptional, (19)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
The price is AU$190
includes taxes & fees
1 Dec - 2 Dec
Magnolias, a chill out place.

Cozy studio in FAN/museums /free parking

Fan District
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
The price is AU$230
includes taxes & fees
16 Dec - 17 Dec
Cozy studio in FAN/museums /free parking

Charming 2-bedroom home, with lake access, in the Richmond metro area.

Quinton
10.0 out of 10, Exceptional, (8)
"House was amazing and host was very kind and helpful"
United States
Aaron R.
The price is AU$259
includes taxes & fees
2 Dec - 3 Dec
Charming 2-bedroom home, with lake access, in the Richmond metro area.

Cozy nest/private porch/museums/free parking

Fan District
10.0 out of 10, Exceptional, (36)
"Great little spot. Was able to walk to restaurants very clean and safe area. Enjoyed our stay and very close to Richmond Raceway!"
United States
Nicole H.
The price is AU$234
includes taxes & fees
4 Dec - 5 Dec
Cozy nest/private porch/museums/free parking

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.
Charming 1-bedroom apartment in Mechanicsville

Sunny, Spacious Suite Green & Shaded Backyard

Northern Barton Heights
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.
The price is AU$391
includes taxes & fees
1 Dec - 2 Dec
Sunny, Spacious Suite Green & Shaded Backyard

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
The price is AU$312
includes taxes & fees
31 Dec - 1 Jan 2026
MV GiaMaria

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

Midlothian
10.0 out of 10, Exceptional, (1)
"Great spot to spend the evening while traveling through! Comfortable space.Host was very helpful through the check in process and my stay.Thanks Pamela!"
United States
Shawn P.
The price is AU$278
includes taxes & fees
20 Dec - 21 Dec
Newly finished basement suite in Midlothian. Very clean and spacious.

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.
The price is AU$347
includes taxes & fees
2 Dec - 3 Dec
Downtown Living in Richmond's Amazing Shockoe Bottom

Modern 5 Bedroom City Retreat + Walkable + Private Baths + Large Groups

2.0 star property
Carver
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.
The price is AU$895
includes taxes & fees
9 Dec - 10 Dec
Modern 5 Bedroom City Retreat + Walkable + Private Baths + Large Groups

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

Richmond
9.6 out of 10, Exceptional, (113)
"Such a cool fun stay. Captain Ron is so friendly and accommodating. Really cool stay for kids!"
United States
Melissa
The price is AU$342
includes taxes & fees
1 Dec - 2 Dec
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

Lovely 2 Bedroom in the Heart of The Fan

Fan District
9.4 out of 10, Exceptional, (73)
"Great location and very comfortable property."
United States
Patricia M.
The price is AU$412
includes taxes & fees
1 Dec - 2 Dec
Lovely 2 Bedroom in the Heart of The Fan

Modern 1 BR Apartment in the Heart of Downtown Richmond with Off-street Parking

2.0 star property
Downtown Richmond
The price is AU$364
includes taxes & fees
1 Dec - 2 Dec
Modern 1 BR Apartment in the Heart of Downtown Richmond with Off-street Parking

Tourist Home of Richmond 1-bedroom Apartment - Church Hill North TH08

Woodville
10.0 out of 10, Exceptional, (1)
"Nice place with a comfy home feel very clean great spot despite the area not being the best being in the home made you not notice definitely five star location "
United States
Alex G.
The price is AU$422
includes taxes & fees
1 Dec - 2 Dec
Tourist Home of Richmond 1-bedroom Apartment - Church Hill North TH08

Downtown Living in Historic Richmond Loft

Downtown Richmond
8.2 out of 10, Very good, (63)
"Perfect property. It was exactly what the pictures represented and our host was extremely helpful and responsive. Would highly recommend! "
United States
Mike L.
The price is AU$422
includes taxes & fees
1 Dec - 2 Dec
Downtown Living in Historic Richmond Loft

Lovely 1-Bedroom Loft with Free Parking and Wifi

Downtown Richmond
8.2 out of 10, Very good, (21)
"Great place, comfortable, clean, close to a lot of fun spots in Richmond"
United States
Derrick C.
The price is AU$347
includes taxes & fees
1 Dec - 2 Dec
Lovely 1-Bedroom Loft with Free Parking and Wifi

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

Virginia Union
10.0 out of 10, Exceptional, (3)
"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.
The price is AU$427
includes taxes & fees
2 Dec - 3 Dec
Private Guest house with Parking and Wi-Fi in a Central Location

Retro bungalow minutes away from historic Old Towne Petersburg!

Petersburg
9.0 out of 10, Wonderful, (8)
"Communication with host was amazing! Cute place. Nice decor. "
United States
Claire F.
The price is AU$225
includes taxes & fees
7 Dec - 8 Dec
Retro bungalow minutes away from historic Old Towne Petersburg!

Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

2.0 star property
Petersburg
9.4 out of 10, Exceptional, (3)
"Big yard."
United States
Michael O.
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$226 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 holiday.

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 holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Iron Bridge Sports Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Chester. Make sure you have time to check out the art and cafés during your trip.

What are some of the best holiday rentals that Chester has to offer?

Great Location. Close to about everywhere .Can't beat the value. Check reviews!: This holiday 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 that you can cook with friends or family.

How many holiday rentals are there in Chester?

With 7 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.