Holiday rentals in Jamestown Island

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Top-rated holiday rentals in Jamestown Island

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Guest favourite
A charming Cape Cod home with a spacious front porch is surrounded by lush greenery and colorful flowers. The sloping roof features three dormer windows, while the well-maintained lawn provides an inviting entryway. The porch is equipped with seating and decorative accents.
Home in Williamsburg
4.83 out of 5 average rating, 296 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

Top guest favourite
A bright living area features a light-colored couch with decorative pillows, complemented by a rustic trunk coffee table. A blue front door can be seen, inviting natural light into the space. Framed botanical prints are displayed on the walls, enhancing the cozy atmosphere.
Home in Williamsburg
4.98 out of 5 average rating, 219 reviews

Eclectic Bungalow 5 mins from Busch & Colonial Wbg

This cozy vintage home is centrally located, just 5 minutes from Colonial Williamsburg & 5 minutes from Busch Gardens. A beautiful blend of classic & modern, your home away from home boasts a large kitchen, full sized laundry, a bathroom with tub, a bedroom with queen bed and desk, a bedroom with two twin beds, & a flex living/bed room that can be closed off featuring a high-end memory foam queen sleeper sofa. Large fenced yard for outdoor fun, it’s the perfect place for your Williamsburg stay!

Top guest favourite
A serene waterfront view of the James River is presented, with a soft layer of mist hovering over the water. A wooden pier extends into the river, lined with posts, while trees and grass frame the scene, enhancing the tranquil atmosphere.
Cottage in Surry
4.9 out of 5 average rating, 102 reviews

“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.

Top guest favourite
The exterior of the house is illuminated by warm string lights, showcasing a spacious two-story structure. Adirondack chairs surround a central fire pit on a gravel patio, providing a cozy gathering area against a backdrop of tree line.
Home in Williamsburg
4.99 out of 5 average rating, 172 reviews

Cheerful 3-bedroom house with parking on premises

Have fun with the whole family at this cozy place. Conveniently located 2 minutes from the Great Wolf Lodge and 10 minutes from Busch Gardens, Colonial Williamsburg, the College of William and Mary, and several parks, this three-bedroom, three baths, big-basement stand alone house lets you explore “the Burg” hassle-free and recharge in a restful space on the back of the Waller Mill reservoir woods. The yard features beautiful landscaping, a large fire pit with solo stove & cozy backyard lights.

Top guest favourite
Home in Toano
4.94 out of 5 average rating, 158 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.

Top guest favourite
A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.
Home in Gloucester Point
4.99 out of 5 average rating, 223 reviews

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

Top guest favourite
A historic house is set amidst gentle greenery, featuring a white exterior with multiple chimneys and a welcoming porch. A white picket fence encircles the lush yard, enriched by tall trees and seasonal foliage, creating a serene and inviting environment.
Home in Williamsburg
5.0 out of 5 average rating, 144 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.

Guest favourite
The exterior of a light gray house is presented, featuring a wide front porch with white railings and steps. Lush green grass surrounds the home, while flower beds add a touch of color. An American flag hangs from a tree nearby, contributing to the welcoming ambiance.
Cottage in Williamsburg
4.94 out of 5 average rating, 286 reviews

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.

Top guest favourite
A spacious colonial-style home is set on manicured grounds, surrounded by trees. The exterior features a welcoming covered porch, large front windows, and well-maintained landscaping, creating an inviting first impression for guests.
Home in Williamsburg
4.94 out of 5 average rating, 222 reviews

The Williamsburg Retreat- Gorgeous Private Acreage

Stunningly manicured and spacious custom built colonial on 6 private acres. - Specializing in large multigenerational family vacations, business and church retreats, and discerning private getaways. Perfect for those desiring comfort, style and space. - Massive covered deck with fire table and outside dinning. Start your day here with coffee and finish it with your favorite wine. -Collect fresh eggs and let the kids run!!! -17 min. to top Williamsburg attractions. -10 min. to outlet mall ;)

Guest favourite
The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.
Apartment in Williamsburg
4.95 out of 5 average rating, 154 reviews

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..

Top guest favourite
A cozy sitting area is highlighted by a floral-patterned couch and a tufted armchair, creating a welcoming space. A small side table with a lamp stands beside the chair, while natural light fills the room through the nearby window.
Cottage in Williamsburg
4.9 out of 5 average rating, 285 reviews

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

Top guest favourite
A lush field is filled with blooming yellow flowers under a clear blue sky. In the background, a red barn is situated near a fence, surrounded by trees that provide a natural border to the landscape.
Farm stay in Williamsburg
4.97 out of 5 average rating, 418 reviews

3 BR Cottage on Mallardee Farm in Williamsburg

Enjoy all the comforts of home during your Williamsburg vacation at Mallardee Farm! Allow us to make our home, your home while you explore all of Williamsburg’s attractions-just a 15 minute drive away! You’ll find that Mallardee Farm will serve as its own attraction with our friendly, rescued farm pets, walking trails through the 57 acre property, complimentary fishing poles, canoe, row boat & kayaks to use on our 7 acre pond. Covid-19 precautions followed.

Popular amenities for Jamestown Island holiday rentals