Chester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester holiday rentals

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
9.8 out of 10, Exceptional, (19 reviews)
"If fishing is your thing, this place seems just the place for you. It's has guest passes to the lake. The bed was very comfortable. IMO, the kitchen needs better cookware."
United States
Kimberly
The price is NZ$321
includes taxes & fees
24 June - 25 June
Charming 2-bedroom home, with lake access, in the Richmond metro area.

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, (119 reviews)
"Very nice stay! Awesome host and quiet neighborhood! Thank you!"
United States
Wes E.
The price is NZ$370
includes taxes & fees
16 June - 17 June
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

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, (237 reviews)
"The houseboat was exactly as described and met as well as exceeding my expectations. Very peaceful, overlooking the river. The bed was comfortable and I love every minute of our stay, just wish it had been longer. We met Capt. Ron on our last night. He is a very nice man and loved talking with him. I hope to return in the future. Barbara and Ben"
United States
Barbara
The price is NZ$370
includes taxes & fees
15 June - 16 June
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Lanexa
10.0 out of 10, Exceptional, (7 reviews)
"First and foremost, the property was excellent! The host, Michael was extremely welcoming and kind. The property is in top condition with new everything! The seclusion and lakefront location was to die for. Highly recommend this property as we will be back! "
United States
Kelly B.
The price is NZ$1,297
includes taxes & fees
30 June - 1 July
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

Red Juniper Retreat

Red Juniper Retreat
New Kent
10.0 out of 10, Exceptional, (26 reviews)
"The house is wonderful, and the owners are amazing! Absolutely love staying here. "
United States
Samantha B.
The price is NZ$1,091
includes taxes & fees
10 June - 11 June
Red Juniper Retreat

Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.4 out of 10, Very good, (17 reviews)
"The home was very clean and very comfortable. Communication was excellent. We would definitely stay here again!"
United States
CHRIS
The price is NZ$701
includes taxes & fees
15 June - 16 June
Luxury Stay! 10 min away from Fort Lee.

The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (1 review)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
The price is NZ$332
includes taxes & fees
21 June - 22 June
The Birdhouse - Cozy Cottage Retreat in Richmond

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (34 reviews)
"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 NZ$556
includes taxes & fees
10 June - 11 June
Downtown Living in Richmond's Amazing Shockoe Bottom

Carytown Gem: Family-Friendly Apartment with Yard

Carytown Gem: Family-Friendly Apartment with Yard
Carytown
9.8 out of 10, Exceptional, (76 reviews)
"Very clean, everything we needed, comfortable beds!!"
United States
Chris K.
The price is NZ$389
includes taxes & fees
10 June - 11 June
Carytown Gem: Family-Friendly Apartment with Yard

Tourist Home of Richmond 1 Bedroom Apartment - Church Hill North TH04

Tourist Home of Richmond 1 Bedroom Apartment - Church Hill North TH04
Woodville
The price is NZ$407
includes taxes & fees
10 June - 11 June
Tourist Home of Richmond 1 Bedroom Apartment - Church Hill North TH04

The Studio@ Eanes Drug-Heart of the Historic District

The Studio@ Eanes Drug-Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (78 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is NZ$315
includes taxes & fees
10 June - 11 June
The Studio@ Eanes Drug-Heart of the Historic District

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

Historic Haven in Church Hill in The Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (67 reviews)
"Amazing stay, every detail was considered. Beautiful home, walkable neighborhood, everything was perfect!"
United States
Becky S.
The price is NZ$336
includes taxes & fees
10 June - 11 June
Historic Haven in Church Hill in The Heart of the Historic District

Lovely 2 Bedroom in the Heart of The Fan

Lovely 2 Bedroom in the Heart of The Fan
Fan District
9.2 out of 10, Wonderful, (84 reviews)
"Easy check in and a pleasant quick stay "
United States
Megan M.
The price is NZ$607
includes taxes & fees
10 June - 11 June
Lovely 2 Bedroom in the Heart of The Fan

Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"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 NZ$515
includes taxes & fees
10 June - 11 June
Cookie B

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
Richmond
10.0 out of 10, Exceptional, (4 reviews)
"Great location! Host responsive!"
United States
Rebekah G.
The price is NZ$483
includes taxes & fees
10 June - 11 June
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard

Nest & Rest/Free Parking/Museum/City Access

Nest & Rest/Free Parking/Museum/City Access
Fan District
9.8 out of 10, Exceptional, (46 reviews)
"Everything was great! And great location!"
United States
Meg S.
Nest & Rest/Free Parking/Museum/City Access

Relax in beautiful second floor apartment with balcony & private fenced yard.

Relax in beautiful second floor apartment with balcony & private fenced yard.
Northern Barton Heights
The price is NZ$651
includes taxes & fees
12 June - 13 June
Relax in beautiful second floor apartment with balcony & private fenced yard.

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, (24 reviews)
"Great place to stay. I will be back"
United States
Bridgette T.
The price is NZ$493
includes taxes & fees
15 June - 16 June
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond

Colorful private guesthouse in charming Richmond with Parking

Colorful private guesthouse in charming Richmond with Parking
Northern Barton Heights
10.0 out of 10, Exceptional, (5 reviews)
"Such a fun place to stay! Room is nicely decorated. Easy check in/check out. Never stayed in this part of RVA before. We will definitely stay here again!"
United States
Teresa M.
The price is NZ$380
includes taxes & fees
10 June - 11 June
Colorful private guesthouse in charming Richmond with Parking

Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (29 reviews)
"Everything was great for our stay! We didn't stay there long but was the perfect location near Carytown. We extended our stay, and the hosts were beyond accommodating. "
United States
Bonnie W.
The price is NZ$249
includes taxes & fees
7 July - 8 July
Carytown cozy nest private room Fenced Yard
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$310 per night. Entering your travel dates in the search wizard you might find 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?

Cozy walkable downtown retreat, 3 minutes to VCU: This holiday home rental outside of Chester is located in the city centre, and offers a selection of games, air conditioning and laundry facilities 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 that you can cook with friends or family.

How many holiday rentals are there in Chester?

With 8 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 Henricus Historical Park and James River 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.