House holiday rentals in Surry County

4.82 out of 5 average rating, 256 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

4.94 out of 5 average rating, 50 reviews

Busch Gardens-River View-fire table-Cornhole

Relax with the whole family at this peaceful place to stay. Just a quick free ferry ride over in your car to Jamestown/Williamsburg for shopping, historical sights, and theme parks. (Busch Gardens/Water Country USA) The ferry again is free and you drive on and off. It runs 24 hrs a day 7 days a week. The home is open yet cozy to enjoy your family and friends. The house is laid out perfect for reunions or family gatherings. The wrap around deck is great for enjoying a cocktail or morning coffee.

4.9 out of 5 average rating, 29 reviews

The Great Gatsby: Pink Flamingo Lounge Retreat!

Welcome to Gatsby's Pink Flamingo Lounge for a memorable stay! Unwind on swings, play the organ, and enjoy a variety of games in this spacious 4-bedroom, 2-bath home that comfortably sleeps up to 10 guests. Located near charming downtown Surry, our unique space features a fully fenced backyard for your furry canine companions. Outdoor activities include cornhole, Tubelox, darts, sprinkler and a baby pool. Handicap accessible with a ramp, this is a one-of-a-kind retreat you won't want to miss!

Top guest favourite

Home in Smithfield

4.97 out of 5 average rating, 36 reviews

Serene 8ac log house W/hot tub!

Welcome to your perfect short-term rental getaway in Smithfield, Virginia! Nestled along the picturesque riverbank, this enchanting log cabin invites you to unwind in the lap of natural beauty. Immerse yourself in the serenity of the surroundings as you indulge in the charm of a gorgeous retreat. **The Cabin:** Discover the allure of rustic elegance with our stunning log cabin, providing a cozy haven for your escape. You’ll be captivated by the tranquility that defines this unique dwelling.

5 out of 5 average rating, 117 reviews

History Art and Nature-110 Acres of Ancient Forest

WILLIAMSBURG AREA, SURRY, VA. 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 winding through the ancient forest. A true hands-on historical experience surrounded by nature. 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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5 out of 5 average rating, 29 reviews

Sleeps 7• 3 miles to Colonial Williamsburg

Minutes away from Historical landmarks & multiple activities. Like Colonial Williamsburg & Busch Gardens. When the day begins to slip away to night enjoy the s’mores I’ve provided for your group. Spend the evening around the Fire-pit telling stories & making memories. This home is perfect for Wedding Parties, Girls or Guys Getaways, or just a private time for 2. From the time you book our home I’m here to help you anyway I can to have a FUN filled, ADVENTUROUS, & a STRESS FREE Vacation.

Top guest favourite

Home in Surry

4.98 out of 5 average rating, 113 reviews

Surry Homeplace

Located a few miles from the ferry to Williamsburg, and one mile from Chippokes State Park, this home has the feel of camping with all the amenities of home! Inside you will find washer and dryer, wifi (this is dish wifi - Zoom will not work and sometimes it is spotty), two full bathrooms, and a fully stocked kitchen. Outside offers a fire pit, a charcoal grill, a fenced area for pets / limit 2 (30 pound max dog, NO CATS ) and plenty of room for parking. Smoking is NOT allowed in the house.

4.86 out of 5 average rating, 86 reviews

Diamonds & Pearls of Williamsburg, VA

Diamonds & Pearls of Williamsburg, VA is an extraordinary home central to many attractions throughout Virginia. It is a private luxurious home with ample yard space for outside gatherings. Have a kingdom experience at this piece of paradise that sleeps 13 people and more. There are two full kitchens, an arcade room, a game room with a pool table, a sauna, two heated vibrating recliners, washer/dryer, a hammock, fire pit, grill, karaoke machine, and more games throughout the house to enjoy.

4.76 out of 5 average rating, 127 reviews

River House on the James

Private 3 bedroom home on bluff overlooking wide stretch of the James River with access to a mile+ long private community beach. Wide open floor plan. Large windows with view of the river and perfect place to see the sunrise. Large yard with fire pit and outside patio seating. A short walk to the beach where you can fish, swim or launch a boat. 15 minute drive to the free car ferry across to Jamestown Settlement with access to Colonial Williamsburg/Busch Gardens/William and Mary.

4.89 out of 5 average rating, 27 reviews

1800's Manor House on the James River

5 Bedroom, 5.5 Bath, 1800's Manor overlooking the James River Eastover was part of a land grant in 1637 from the King of England to Henry Brown. Over the years, land was both acquired and subdivided into different parcels, leaving 283 acres, including the Manor house. Although the Manor house was not Henry Brown's house, it still has been of historical importance to many people. The Manor house was built in the 1880's and is currently owned and operated by The Edge Christian Camp, Inc.

5 out of 5 average rating, 15 reviews

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.