Find Romantic Hotels in Chester, VA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Romantic Hotels

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Chester Romantic Hotels

Property entrance
Linden Row Inn

Linden Row Inn

3.0 star property
Downtown Richmond
9.2 out of 10, Wonderful, (1285)
"Great stay, location, & customer service. "
United States
Rosa
The price is SAR 432
SAR 503 total
includes taxes & fees
14 Dec - 15 Dec
Linden Row Inn
Lobby
The Jefferson Hotel

The Jefferson Hotel

5.0 star property
Downtown Richmond
9.8 out of 10, Exceptional, (1000)
"Excellent dining, beautiful hotel, very convenient amenities "
United States
Karin
The price is SAR 1,107
SAR 1,287 total
includes taxes & fees
1 Jan - 2 January 2026
The Jefferson Hotel
Exterior
Omni Richmond Hotel

Omni Richmond Hotel

4.0 star property
Downtown Richmond
9.0 out of 10, Wonderful, (1265)
"Wonderful stay!!"
United States
Kristina
The price is SAR 635
SAR 738 total
includes taxes & fees
14 Dec - 15 Dec
Omni Richmond Hotel
Property grounds
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)
"Such a cool fun stay. Captain Ron is so friendly and accommodating. Really cool stay for kids!"
United States
Melissa
The price is SAR 432
SAR 833 total
includes taxes & fees
8 Dec - 9 Dec
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Courtyard
Hilton Richmond Downtown

Hilton Richmond Downtown

4.0 star property
Downtown Richmond
8.4 out of 10, Very Good, (1005)
"Everything was excellent"
United States
Michael
The price is SAR 551
SAR 641 total
includes taxes & fees
14 Dec - 15 Dec
Hilton Richmond Downtown
Lobby
DoubleTree by Hilton Richmond - Midlothian

DoubleTree by Hilton Richmond - Midlothian

4.0 star property
North Chesterfield
8.0 out of 10, Very Good, (1000)
"Clean room and friendly staff."
United States
Itarsha
The price is SAR 475
SAR 553 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Richmond - Midlothian
Property grounds
A VERY NICE 43' YACHT WITH LONG RIVER VIEWS AND ONSITE RIVERSIDE DINING

A VERY NICE 43' YACHT WITH LONG RIVER VIEWS AND ONSITE RIVERSIDE DINING

Richmond
10.0 out of 10, Exceptional, (17)
"Simply a beautiful spot on the James River with a great restaurant and live music. This is an older boat and boats are different than a house so keep that in mind if you havent been around boats. Ron is a wonderful host who is extremely responsive. He looks out for his guests and is full of wonderful stories. We'll be back!"
United States
Eric B.
The price is SAR 469
SAR 901 total
includes taxes & fees
31 Dec - 1 January 2026
A VERY NICE 43' YACHT WITH LONG RIVER VIEWS AND ONSITE RIVERSIDE DINING
Exterior
Four Points by Sheraton Richmond

Four Points by Sheraton Richmond

3.5 star property
North Chesterfield
8.6 out of 10, Excellent, (1001)
"Very friendly staff and clean"
United States
Annette
The price is SAR 402
SAR 467 total
includes taxes & fees
21 Dec - 22 Dec
Four Points by Sheraton Richmond
Front of property - evening/night
Quirk Hotel Richmond

Quirk Hotel Richmond

4.0 star property
Downtown Richmond
8.8 out of 10, Excellent, (1003)
"Great great people/staff!!"
United States
Samantha
Quirk Hotel Richmond
2 bars/lounges, lobby lounge
Richmond Marriott

Richmond Marriott

3.5 star property
Downtown Richmond
8.8 out of 10, Excellent, (1000)
"The room was clean. Staff were friendly. Breakfast was delicious! We loved the Christmas decorations. "
United States
Christina
The price is SAR 624
SAR 726 total
includes taxes & fees
14 Dec - 15 Dec
Richmond Marriott
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.
View all properties

Top Chester Hotel Reviews

Linden Row Inn

Linden Row Inn

10/10 Excellent
"Fantastic bed. Great shower. "
William 1-night trip
Posted 3 days ago
Linden Row Inn

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Chester?
Are you looking for a romantic getaway? Our guests also enjoy Chester for its restaurants and shopping. You might consider checking out some of the nearby sights and attractions such as Iron Bridge Sports Park, James River, or Henricus Historical Park. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Chester?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 76°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Chester is 50 inches.
What is there to do in Chester?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all that Chester has to offer. If you and your partner are interested in sampling the area's cuisine, you'll love Chester for its array of dining options. A visit to Iron Bridge Sports Park, James River, or Henricus Historical Park might be just the ticket when you're checking out the sights.
What's the best way to get to Chester and around town during my romantic getaway?
These transportation options in Chester might help your romantic trip go off without a hitch: To get to Chester, book a flight to Richmond Intl. Airport (RIC), which is the closest major airport, located 12.2 mi (19.6 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.