An aerial view of a residential area with houses, roads, and a water tower.

Find Romantic Hotels in Chester, VA from CA $304

  • 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
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Chester romantic hotels

A marina with docked boats, a covered structure, and a forested hillside in the background.
A cozy room with a fireplace, a television, a bookshelf, and a bed.
A boat deck with seating, a pool, and a view of the surrounding landscape.
A bedroom with a large bed, a window with a view of boats, a lamp, and framed pictures on the wall.

1. 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
United States
Allison K.
CA $163
CA $304 total
includes taxes & fees
Oct 22 - Oct 23
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.
A cozy corner with a table and chairs, a vase with flowers, and a fireplace.
A marina with several boats docked, a covered area, and a building with a red roof in the background.
A boat deck with seating, a pool, and a view of the surrounding landscape.

2. 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
United States
Ashley Jo P.
CA $163
CA $304 total
includes taxes & fees
Oct 22 - Oct 23
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A bakery with a glass display case filled with pastries and a chalkboard menu listing items like gelato and coffee.
A bedroom with a fireplace, a wooden dresser, a large mirror, and a bed.
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.
A patio with brick flooring, a stone pathway, and outdoor furniture.

3. Downtown, 2 Parking spaces, Historic Beauty

Downtown, 2 Parking spaces, Historic Beauty
Downtown Richmond
United States
Samuel V.
CA $344
CA $688 total
includes taxes & fees
Oct 19 - Oct 20
Downtown, 2 Parking spaces, Historic Beauty
View all properties

Top Chester Hotel Reviews

The Jefferson Hotel

The Jefferson Hotel

10/10 Excellent
"Clean room; easy self park"
rich 1-night trip
Posted 15 hours ago
The Jefferson Hotel
Linden Row Inn

Linden Row Inn

10/10 Excellent
"Having a shuttle to the airport would have been an added bonus"
Joan 2-night trip
Posted 2 days ago
Linden Row Inn

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.

Explore a world of travel with Expedia