Holiday rentals with outdoor seating in Surry County

4.83 out of 5 average rating, 230 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, 17 reviews

Home in Spring Grove

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, Mega Bloks, 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!

4.95 out of 5 average rating, 120 reviews

Condo in Williamsburg

Kingsmill 2bd2ba Condo on Golf Course 9th Fairway!

This beautiful, 2B2Ba condo is 1400 sq.ft. in the exclusive Kingsmill neighborhood. This 1st floor unit has two master suites w/ king beds. One features a luxurious bathroom w/ a walk-in shower & dual shower heads, the other has a shower/tub combo as well as a private patio, stepping out onto the 9th Fairway. The open-concept living space has dining for 6, a queen sleeper sofa, a fully stocked kitchen, and an additional private patio. Golf course views from anywhere in the main living space!

4.9 out of 5 average rating, 62 reviews

Cottage in Surry

“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.

Superhost

Condo in Williamsburg

4.94 out of 5 average rating, 123 reviews

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

5 out of 5 average rating, 126 reviews

Farm stay in Smithfield

Cottage at Timberline Ranch in Smithfield Virginia

Relax on a private 30 acre horse farm. 8 miles from historic Smithfield, VA Spacious bedroom, double window with view of horse pastures. Room darkening drapes. Full length mirror with lighted makeup mirror, air purifier, ample sheets, blankets and pillows. Full kitchen like brand new and well stocked with necessities; cookware, dishes, paper products, spices. Large bathroom with ceiling heater, towel warmer, well stocked with towels and necessities. Washer and dryer, detergent supplied.

5 out of 5 average rating, 13 reviews

Home in Smithfield

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, 23 reviews

Sleeps 7 & only 6.4 Miles to Busch Gardens

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.

5 out of 5 average rating, 109 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, 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.

4.98 out of 5 average rating, 66 reviews

3BR home across from the Williamsburg Winery

Enjoy a fully renovated 3-bedroom home directly across from the Williamsburg Winery. “Grape Views” is centrally located with just an 8 minute drive to Colonial Williamsburg/William & Mary campus, a 15 minute drive to Busch Gardens/Water Country, and less than a mile to the private Williamsburg Airport. Enjoy picturesque views of the winery whether dining in the newly remodeled kitchen or outside on the charming back patio. There is a strict no pets policy.

4.89 out of 5 average rating, 9 reviews

Home in Wakefield

Magic on Main

Lovingly renovated with bold colors and thoughtful decor. You are sure to love the small quirks found in this home. Fully furnished and ready for long term stays. 2 bedrooms, 2 full baths and a dedicated office space. There is a pullout bed in the living room that can be utilized as a 3rd bed. Landscaping crew comes once a week on Tuesdays. Pets welcome with prior approval given by host. Long term stay pet fee can be negotiated.