Chester Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chester holiday rentals

Fridge, microwave, oven, stovetop

The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres

The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres
Charles City County
10.0 out of 10, Exceptional, (4 reviews)
"Amazing Stay. Very helpful & has everything you need . We will be coming back soon . Thank You James ! "
United Kingdom
Travis K.
The price is HK$1,617
HK$3,177 total
includes taxes & fees
4 Feb - 5 Feb
The Vibe: 3BR- Wedding-Ready Retreat with King Comfort & Fire Pit on 10 acres
Lobby

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, (113 reviews)
"2nd time staying at this property and definitely won’t be the last! Amazing location and great host."
United States
Alexis S.
The price is HK$898
HK$1,651 total
includes taxes & fees
4 Feb - 5 Feb
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
1 bedroom, in-room safe, free WiFi, bed sheets

Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.4 out of 10, Exceptional, (21 reviews)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
The price is HK$499
HK$927 total
includes taxes & fees
4 Feb - 5 Feb
Magnolias, a chill out place.
Fridge, microwave, oven, stovetop

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
10.0 out of 10, Exceptional, (58 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is HK$976
HK$1,294 total
includes taxes & fees
4 Feb - 5 Feb
The Studio@ Eanes Drug
Property grounds

Sunny, Spacious Suite Green & Shaded Backyard

Sunny, Spacious Suite Green & Shaded Backyard
Northern Barton Heights
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely no issues during my brief stay with my host. I and my dog particularly enjoyed the backyard space. "
United States
Danielle A.
The price is HK$574
HK$1,773 total
includes taxes & fees
4 Feb - 5 Feb
Sunny, Spacious Suite Green & Shaded Backyard
Private kitchen

Forest Hill Apt - 202

Forest Hill Apt - 202
2.0 star property
Woodville
The price is HK$937
HK$1,537 total
includes taxes & fees
12 Feb - 13 Feb
Forest Hill Apt - 202
Interior

Superb 3BR W/Balcony Near Capitol Center

Superb 3BR W/Balcony Near Capitol Center
Chimborazo
9.6 out of 10, Exceptional, (14 reviews)
"I didn’t love the street parking but other than that it was a nice stay."
United States
K J.
The price is HK$921
HK$3,205 total
includes taxes & fees
11 Feb - 12 Feb
Superb 3BR W/Balcony Near Capitol Center
Outdoor dining

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, (4 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 HK$820
HK$1,607 total
includes taxes & fees
4 Feb - 5 Feb
Colorful private guesthouse in charming Richmond with Parking
Interior

The Cozy Bungalow: free parking w/fully fenced yard

The Cozy Bungalow: free parking w/fully fenced yard
Richmond
10.0 out of 10, Exceptional, (2 reviews)
"Great location! Host responsive!"
United States
Rebekah G.
The price is HK$797
HK$1,957 total
includes taxes & fees
4 Feb - 5 Feb
The Cozy Bungalow: free parking w/fully fenced yard
Living area

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

Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
Petersburg
9.4 out of 10, Exceptional, (3 reviews)
"Big yard."
United States
Michael O.
The price is HK$1,118
HK$2,671 total
includes taxes & fees
6 Feb - 7 Feb
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
Smart TV

Charming 3-bedroom townhome with WiFi in delightful Richmond

Charming 3-bedroom townhome with WiFi in delightful Richmond
Jahnke
10.0 out of 10, Exceptional, (4 reviews)
"Townhouse was awesome. Plenty of room for 6 people. Pet friendly. Quiet neighborhood. Host Jordan was very helpful and available when needed. We all loved our stay. Would stay again. "
United States
Betty C R.
The price is HK$1,033
HK$2,332 total
includes taxes & fees
4 Feb - 5 Feb
Charming 3-bedroom townhome with WiFi in delightful Richmond
Interior

Carytown Gem: Family-Friendly Apartment with Yard

Carytown Gem: Family-Friendly Apartment with Yard
Carytown
9.8 out of 10, Exceptional, (67 reviews)
"Very nice"
United States
Mary T.
The price is HK$789
HK$1,680 total
includes taxes & fees
4 Feb - 5 Feb
Carytown Gem: Family-Friendly Apartment with Yard
1 bedroom, WiFi

Charming 1-bedroom apartment in Mechanicsville

Charming 1-bedroom apartment in Mechanicsville
Mechanicsville
10.0 out of 10, Exceptional, (3 reviews)
"Had a great stay while fishing the james river. "
United States
Travis D.
The price is HK$625
HK$1,079 total
includes taxes & fees
8 Feb - 9 Feb
Charming 1-bedroom apartment in Mechanicsville
Terrace/patio

Urban Bloom/King Bed/2TVs/Free Parking/Museums

Urban Bloom/King Bed/2TVs/Free Parking/Museums
Fan District
9.8 out of 10, Exceptional, (48 reviews)
"This property was just what we needed for our quick getaway to Richmond. Everything was either walkable or a short drive away. Mei was a very responsive host, which was awesome. The house was clean and comfy as well. "
United States
Jessica D.
The price is HK$1,711
HK$2,550 total
includes taxes & fees
6 Mar - 7 Mar
Urban Bloom/King Bed/2TVs/Free Parking/Museums
Property grounds

Stylish Loft - Shockoe Bottom - Walk to Canal - Historic Apartment

Stylish Loft - Shockoe Bottom - Walk to Canal - Historic Apartment
Downtown Richmond
10.0 out of 10, Exceptional, (1 review)
The price is HK$772
HK$2,338 total
includes taxes & fees
9 Feb - 10 Feb
Stylish Loft - Shockoe Bottom - Walk to Canal - Historic Apartment
Dining

Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (27 reviews)
"Mei, the host, is very communicative and the apartment is spacious, clean and nicely appointed. Awesome location too. You can walk to everything in Carytown. "
United States
Heather H.
The price is HK$531
HK$1,068 total
includes taxes & fees
4 Feb - 5 Feb
Carytown cozy nest private room Fenced Yard
Fridge, microwave, oven, stovetop

Historic Haven in Church Hill

Historic Haven in Church Hill
Church Hill
10.0 out of 10, Exceptional, (50 reviews)
"Great place, great location!"
United States
Janet F.
The price is HK$1,054
HK$1,384 total
includes taxes & fees
8 Feb - 9 Feb
Historic Haven in Church Hill
Front of property

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 HK$1,709
HK$2,338 total
includes taxes & fees
10 Feb - 11 Feb
Cookie B
Exterior

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, (3 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 HK$3,124
HK$5,956 total
includes taxes & fees
28 Feb - 1 Mar
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Exterior

Red Juniper Retreat

Red Juniper Retreat
New Kent
10.0 out of 10, Exceptional, (24 reviews)
"Excellent!"
United States
H
The price is HK$2,346
HK$5,571 total
includes taxes & fees
8 Feb - 9 Feb
Red Juniper Retreat
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

Country Inn & Suites by Radisson, Richmond I-95 South, VA

Country Inn & Suites by Radisson, Richmond I-95 South, VA

10/10 Excellent
"Courteous staff, easy check in and check out."
Claudine 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Richmond I-95 South, VA

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

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?

Super Location. Close to about everywhere .Great value.Over 200 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 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 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.