
Holiday houses in Surry County
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Top-rated holiday rentals in Surry County
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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
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Winery | Colonial Williamsburg | Busch Gardens 3BR
Wake up overlooking the grape vines of the Williamsburg Winery! Spend your day exploring the Historic Triangle, William & Mary, or the theme parks. Return to enjoy a glass of wine on the patio as you regroup for another day of fun! Perfect for: -Multi-generational family vacations to Williamsburg -William & Mary visits (Graduation, Homecoming) -Winery weekend (couples, girls' trips, weddings) -Golf trips (Golden Horseshoe, Kingsmill, Kiskiack) -Thrill seekers (Water Country and Busch Gardens)
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“Magnolia Cottage” on the River
Perched on a bluff high above the James River this charming rehabbed cottage is an idyllic escape from everyday life. This spot is for travelers who seek a step back in time to a simpler life. You’ll be surrounded by woods, water and a growing flower farm. The set up is unique in that the cottage itself holds living and sleeping space while your own designated bathroom and outdoor hot water shower are a short walk across the yard to a tool shed turned luxury bath and shower under the open sky.
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Cozy Farm Cottage with Horses, Fire Pit, & Trails
Escape to Timberline Ranch, a 30-acre horse farm near historic Smithfield. Horses and goats are visible from multiple windows. Your bedroom is cozy with room-darkening drapes, plenty of blankets and pillows. The kitchen is well stocked. Coffee station stocked and to-go cups. Bathroom has a ceiling heater, towel warmer, essentials. W/D with detergent. Step out to the front porch rocking chairs, fire pit (wood incl), and picnic table. Explore trails, follow the creek, and hunt for hidden gnomes.
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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.
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Colonial williamsburg house
During this time of global crisis, we wish to assure all guests that we have been faithfully following the CDC recommendations to avoid the spread of COVID-19. We are cleaning all surfaces in our house with disinfectant, washing bedding with Clorox, and providing antibacterial hand soap for our guests. Close to shopping and restaurants with take out service. Ample outdoor space with fire pit, grill, deck and covered porch. Fast internet service, there is a smart tv connected to a antenna.
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The Hotel at The Surry Seafood Co Room 1
Beautiful efficiency hotel room overlooking Gray's Creek in Surry, VA with separate living and sleeping rooms. Private queen bed with walkin closet. Living area with pull out queen size sofa. Kitchenette with refrigerator and microwave in each room. Situated above a very nice seafood restaurant. Private balcony overlooks the marina and marshes. Fishing pier and public boat launch on site. Sleeps 4. Private entrance. 5.3% Sales tax will be added to final pricing per local laws.
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2 Bedroom Stylish Kingsmill condo
Located in the beautiful Kingsmill resort, this charming two bedrooms, two baths condo with stunning seasonal views over the pond is only a few minutes away from CW, Busch Gardens, water country, William and Maryand other Williamsburg attractions. All Kingsmill amenities are not included as they are strictly for Kingsmill residents Guests have access to the Spa and to the Mill Coffee House which is within walking distance from the condo and serves breakfast and lunch every day..
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Coleman Cottage
Enjoy easy access to everything from this perfectly located home base. This recently updated cottage is steps away from our local farmers market and a short ride to all that Williamsburg has to offer. Walking distance to local grocery store and local restaurants. Minutes drive to Colonial Williamsburg, Jamestown Island, Billsburg and other outdoor breweries. William and Mary is minutes away. Newtown shops and restaurants is a short drive. Bush Gardens is a 10 minute drive
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Analog Private Beach on 10 Acres
After a fun drive down a curvy forest flanked road, you emerge into the sunlight, dogleg around another field and enter the woods on a gravel road. When you get to the gate you can vaguely see the vastness of the James River and you hear the sound of a light breeze as it tumbles amid the leaves. You work the gate and as you push it open you realize the time you will spend on this sacred land connects you to more than 100 years of family gathering and balance with nature.
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Cute 1-bdrm tiny house in the country w/firepits
Enjoy the sounds of nature at this Studio-style Tiny House with heat for wintry nights and air conditioning. Tiny House features a kitchenette with a mini fridge, microwave, portable electric stove, coffee pot and grill. Plus a kitchen sink and running deep well water. Relax on the porch. This sleeps 2 privately and with a full size bed and a sleeper sofa. Inside you will find a new toilet for your convenience, plus a outdoor bathroom, shower and wash station.
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Comfy 1BR w pond view Kingsmill
Be close to everything when you stay at Kingsmill’s centrally-located gated community. Minutes from Busch Gardens, Colonial Williamsburg, Jamestown, Yorktown and College of William & Mary. At end of busy day, relax on your private balcony overlooking pond. If you are looking for comfort, convenience, cleanliness and security, this is your place! Sorry, no pets.
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Popular amenities for Surry County holiday rentals
Other great holiday rentals in Surry County

Serene 8ac log house W/hot tub! Spacious 4BR/2BA
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Waterfront on the James 4,100 SF near Williamsburg
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Riverfront Oasis | Kayaks, Private Beach, & More
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The Great Gatsby: Pink Flamingo Lounge Retreat!
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The Holiday Home • 3 full baths • 8 beds
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Cozy 2BR Condo in Williamsburg
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Two King Suites - Bunk Rm - Ferry
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Spacious 3BR Condo in Gated Community
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Destinations to explore
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Pocahontas State Park
- Outlook Beach
- Greater Richmond Convention Center
- Old Dominion University
- Norfolk Botanical Garden
- Regent University
- First Landing Beach
- Brown's Island
- Colonial Williamsburg's Merchants Square
- Virginia Holocaust Museum
- The National
- Forest Hill Park
- Libby Hill Park
- The Mariners' Museum
- Town Point Park
- The Poe Museum
- Nauticus
- Altria Theater





