Holiday rentals in Jamestown Island

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Top-rated holiday rentals in Jamestown Island

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Top guest favourite
A cozy bedroom features a king-size bed with crisp white linens and decorative pillows. A large window offers a view of a green space beyond, with a sitting area including a chair and small table. A 50" TV and coffee station are positioned on a wooden dresser.
Apartment in Williamsburg
4.94 out of 5 average rating, 217 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

Top guest favourite
A winding gravel pathway is illuminated by soft lighting, bordered by lush greenery. String lights are hung above, casting a warm glow over the area, which is surrounded by trees and plantings. A staircase leads to an elevated area in the background.
Guest house in Gloucester County
4.97 out of 5 average rating, 238 reviews

Stylish Creekside Cabin w/ HotTub, Parklike views.

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Top guest favourite
Home in Toano
4.94 out of 5 average rating, 154 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
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, 170 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
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 out of 5 average rating, 142 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
A spacious living area features large windows providing views of Gray's Creek. A comfortable sofa and a cozy chair are positioned alongside a coffee table on a decorative rug. A private balcony is accessible through sliding glass doors, enhancing the connection to the scenic surroundings.
Flat in Surry
4.84 out of 5 average rating, 123 reviews

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.

Superhost
The exterior of a cozy apartment is depicted, featuring a white facade with green shutters. A small porch is visible, accompanied by a sign indicating the apartment's name. Lush greenery and floral plants frame the entrance, while a gravel pathway leads to the door.
Flat in Williamsburg
4.83 out of 5 average rating, 516 reviews

The Nook

Enjoy a getaway in this cozy 1 bedroom apartment attached to a classic 1940s Cape Cod home minutes from Colonial Williamsburg and Jamestown. You'll be within biking distance to many local attractions such as Williamsburg Winery, Jamestown Island, Jamestown Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The Nook was completely refinished in 2020. Need more space or traveling with a group? Inquire about our other units.

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, 150 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..

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, 282 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

Guest favourite
A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.
Cabin in Cape Charles
4.96 out of 5 average rating, 253 reviews

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

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, 413 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.

Top guest favourite
A bright guestroom is furnished with two double beds, each featuring a light-colored quilt. Nightstands with lamps are positioned beside the beds. A large window offers views of greenery, with soft curtains complementing the decor.
Apartment in Williamsburg
4.96 out of 5 average rating, 157 reviews

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.

Popular amenities for Jamestown Island holiday rentals