
Holiday houses in Charles City
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Top-rated holiday rentals in Charles City
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Cap 2 Cap Cottage VA Capital Trail Charles City
Cap 2 Cap Cottage - Rural oasis awaits in a NEWLY RENOVATED COTTAGE on 6 acres. 52 mile Virginia Capital Trail (Jamestown - Richmond) is only 3/10 of a mile away.Primary suite w/ 1 King bed. Add'l bedroom w/ 1 Queen bed. 2 full baths. Great Wifi, Smart TV, fully equipped kitchen, private deck. Fantastic restaurant/brewery Indian Fields Tavern is 3 miles away. Perfect stay for cyclists ,history lovers or just unwinding. NO Smoking or parties. Colonial Williamsburg 24 miles, Richmond is 30 miles .
4.99 out of 5 average rating, 138 reviews
Unique 2 BR. Barn Apt. with Incredible views
Want a quiet apt. getaway in the woods? Views from every room overlooking fields with woods, deer and wildlife, 2 day min. stay, 3 day holidays, or extended stays permitted if available. A luxurious 2 BR apt., new 75” Qled HDTV, located upstairs in a unique barn *Loaded with amenities nestled 1/2 mile down a gravel drive, with scenic woods and wildlife. Sleeps up to 4 people + child *2 Bedrooms w/ceiling fans *HDTVs *new king bed in master *W/D *Low cleaning fee *See our 5 Star reviews
4.98 out of 5 average rating, 138 reviews
Colonial Retreat
Enjoy a getaway in our 1940 Cape Cod home minutes from Colonial Williamsburg & Jamestown. Within biking distance to many attractions such as Williamsburg Winery, Jamestown Island & Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The house was refinished in 2021; you'll find an updated kitchen, smart TVs, large back patio & front porch. Please read the house rules before booking. No smoking. Need more space? Inquire about our other units
4.83 out of 5 average rating, 297 reviews
"Waterfront! The Lilypad on Mill Creek-Near Wmsbg"
The Lily Pad on Mill Creek provides lovely waterfront views, private dock, wifi, private parking and all the comforts of home! The entire home has been recently renovated, including new HVAC, electric and plumbing and all new appliances! Secluded location to enjoy fishing, kayaking, (kayaks and life vests provided)swimming, canoeing and enjoying the wildlife.Just minutes away from local restaurants and there are two local boat ramps, less than ten minutes away. Have your boat at your fingertips!
4.93 out of 5 average rating, 126 reviews
Serenity Over 5 Acres: Historic Triangle Haven
*4500 sq.ft. fully furnished house w/ 4 bedrooms & loft. *Includes all the amenities you need to enjoy a peaceful stay. * Unwind w/ friends & family in this modern retreat nestled on 5 acres in the woods w/ waterfront view & a fire pit. *You’ll enjoy the secluded area & yet be close to the bustle & hustle of what Williamsburg can offer. *Only 15-20 minutes to major attractions such as, Colonial Williamsburg, Bush Gardens, Jamestown, Yorktown, outlet mall. *Master bathroom only has a bath tub.
4.94 out of 5 average rating, 160 reviews
History Art and Nature-110 Acres of Ancient Forest
WILLIAMSBURG AREA, SURRY, VA. CELEBRATE AMERICA'S 250TH by living in the historic family home of a Revolutionary War soldier! Lightwood Forest is a beautiful historic house nestled in 110 acres of private woodland preserve. Surround yourself with history, antiques, art and nature, and over two miles of private hiking trails. Lightwood Forest is in rural Surry County, on the south side of the James River, a short, free car ferry ride from Williamsburg and Jamestown, which runs 24/7, all year.
5.0 out of 5 average rating, 145 reviews
The Bike Path House! VA Capital Trail Access Fun!
Welcome to the "Bike Path" house! Whether you come to ride, walk, tour nearby plantations & vineyard, or are just looking for some quiet relaxation, this is the spot for you! Located conveniently across from the enchanting Capital Trail that connects Richmond to Williamsburg, on historic Route 5! Have an adventure & explore the 12 acres of woods behind the house! Easy and very scenic drive to Richmond or Williamsburg! The house is stocked w/ games for you to enjoy after a day of outdoor fun!
4.75 out of 5 average rating, 105 reviews
Tiny Red Barn on The Reservoir-Near Williamsburg
Important: NO 3RD PARTY RES. Tiny Red Barn is a labor of love built by us for you on the Diascund Reservoir with water views, wooded trails and sunsets. We feel like we're on vacation every day of the year and look forward to sharing our 26 acres with you. Heavily wooded land with rolling trails, birds, deer, squirrels, turtles, chickens, mini donkeys and bees. A large amount of our property sits on the Diascund Reservoir which provides a whole other side of nature. Opened April 1, 2021.
5.0 out of 5 average rating, 111 reviews
Sunset Retreat *Waterfront / Spacious*
Sunset Retreat is a perfect place for family and friends to visit with plenty of indoor and outdoor spaces available for quiet time or group activities. We have, a playground area, cornhole boards, a firepit, kayak's, and a 2-person wide bottom canoe for your enjoyment. We have some life vests at the dock you're welcome to use too. * INTERNET - Country living, you can usually get on FB and such, but streaming, gaming, and watching movies may be hit and miss on the T Mobile internet provider.
5.0 out of 5 average rating, 109 reviews
Lovely space above barn on a working farm!
Getaway to the country!! Suitable for a 4 adults or families of 5. Wake up to beautiful sunrises. Spend a peaceful day surrounded by farm and wild animals. Enjoy the dark night sky lit with millions of stars after watching the sunset. Above our barn is a two bedroom, one bath living space with a living area open to a kitchen fit for every cook!! Located near Williamsburg, Jamestown and Yorktown, Busch Gardens and Water Country, the Virginia Capitol Trail and 5,217 acre wildlife refuge.
4.99 out of 5 average rating, 161 reviews
Kelly's Comfortable Quinton Home
Welcome to Kelly’s Cottage, a charming retreat nestled among century-old oaks in a peaceful neighborhood. This cozy, mid-20th-century brick rancher offers a warmth and comfort you won’t find in modern homes. Enjoy a cup of cocoa by the bonfire in spring or fall, or explore nearby attractions, including local wineries, restaurants, microbreweries, and Civil War battlegrounds. Pet-friendly with a spacious backyard, Kelly’s Cottage is the perfect spot to unwind and enjoy the area’s beauty!
4.93 out of 5 average rating, 137 reviews
TooFine Lakehouse, pet friendly waterfront cottage
Cute & cozy (tiny) waterfront cottage nestled in a pine forest. Situated on an almost 3 acre point on the Diascund Reservoir this is THE perfect spot to get away from it all & still be in the middle of everything! Options abound - fishing from the dock, bird watching, canoeing, roasting marshmallows around the fire pit, swinging in the hammocks, napping on the screened in porch, grilling on the patio, reading in the loft, playing games (inside & out), or just chill & feel the vibe.
4.98 out of 5 average rating, 167 reviewsPopular amenities for Charles City holiday rentals
Other great holiday rentals in Charles City

Capital Bike Trail Stay | Cozy 2BR Cottage
4.96 out of 5 average rating, 56 reviews
Welcome to the Vibe—Modern 3BR House on 10 acres
5.0 out of 5 average rating, 24 reviews
The Marston Farmhouse
4.94 out of 5 average rating, 63 reviews
The House on the River!
4.92 out of 5 average rating, 36 reviews
Wooded Oasis on the way to the beach!
4.95 out of 5 average rating, 59 reviews
Lake access community convenient to everything!
4.92 out of 5 average rating, 38 reviews
BlakeMoore
5.0 out of 5 average rating, 31 reviews
NEW Hot Tub+Sauna w/Long Range Lake Views+Fire Pit
5.0 out of 5 average rating, 4 reviewsDestinations to explore
- New York Holiday rentals
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- Busch Gardens Williamsburg
- Kings Dominion
- Buckroe Beach
- Water Country USA
- Jamestown Settlement
- Pocahontas State Park
- Outlook Beach
- Greater Richmond Convention Center
- Brown's Island
- Colonial Williamsburg's Merchants Square
- The National
- Virginia Holocaust Museum
- Forest Hill Park
- Libby Hill Park
- The Mariners' Museum
- The Poe Museum
- Altria Theater
- Hampton University
- Science Museum of Virginia
- Virginia Living History Museum
- Children's Museum of Richmond
- Virginia State Capitol-Northwest
- American Civil War Museum
- Fort Monroe National Monument





