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Places to stay near Jamestown Settlement

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Top-rated holiday rentals near Jamestown Settlement

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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

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

4.83 out of 5 average rating, 298 reviews
Top guest favourite
A bright living area features a spacious sectional sofa with accent pillows, complemented by a stylish armchair. A round coffee table sits on a soft area rug, and natural light filters through the windows. The space is accented by neutral walls and wooden flooring.
Home in Williamsburg

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)

4.99 out of 5 average rating, 101 reviews
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

“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.

4.9 out of 5 average rating, 104 reviews
Top guest favourite
Home in Toano

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.

4.94 out of 5 average rating, 160 reviews
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

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.

5.0 out of 5 average rating, 145 reviews
Top 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

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.

4.94 out of 5 average rating, 287 reviews
Guest favourite
A serene landscape captures a sunset over the James River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the view, and a gently sloping green lawn leads toward the riverbank, enhancing the tranquil atmosphere.
Apartment in Williamsburg

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.

4.93 out of 5 average rating, 152 reviews
Top guest favourite
The exterior of a large black barn is shown under a clear blue sky. Two wooden doors are open, revealing a welcoming entrance. Flower pots are arranged along the path, while two wooden chairs are positioned in front, inviting relaxation amidst a tranquil rural setting.
Farm stay in Charles City

Lovely space above barn on a working farm!

Getaway to the country!! Suitable for a 4 adults or families of 5. Wake up to beautiful sunrises. Spend a peaceful day surrounded by farm and wild animals. Enjoy the dark night sky lit with millions of stars after watching the sunset. Above our barn is a two bedroom, one bath living space with a living area open to a kitchen fit for every cook!! Located near Williamsburg, Jamestown and Yorktown, Busch Gardens and Water Country, the Virginia Capitol Trail and 5,217 acre wildlife refuge.

4.99 out of 5 average rating, 162 reviews
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

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.

4.84 out of 5 average rating, 126 reviews
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

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..

4.95 out of 5 average rating, 155 reviews
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

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

4.9 out of 5 average rating, 289 reviews
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

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.

4.97 out of 5 average rating, 419 reviews

Popular amenities for holiday rentals near Jamestown Settlement

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Jamestown Settlement

Jamestown Settlement

158 locals recommend

Billsburg Brewery

31 locals recommend

Jamestown Beach Event Park

19 locals recommend

Apartment rentals with wifi

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

Comfy 1BR w pond view Kingsmill

4.96 out of 5 average rating, 163 reviews
Top guest favourite
A tranquil lakeside scene captures two individuals on paddleboards gliding across calm water. Sandy shores are lined with chairs, offering a peaceful spot to relax. In the background, a spacious building features a wraparound deck, providing views of the serene landscape.
Apartment in Williamsburg

Walk to beach lovely 2/2 in "Kingsmill on James"

4.97 out of 5 average rating, 119 reviews
Superhost
A cozy bedroom features a spacious bed with a soft white duvet and multiple pillows. Twin bedside tables hold lamps that illuminate the room. Soft yellow walls and a sloped ceiling create a bright atmosphere. Natural light filters in, enhancing the inviting space.
Apartment in Williamsburg

Book a Piece of History at Kingsmill Williamsburg

4.8 out of 5 average rating, 160 reviews
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

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

4.95 out of 5 average rating, 224 reviews
Guest favourite
Apartment in Williamsburg

Colonial Williamsburg Spacious 4 Bedroom Suite!

4.91 out of 5 average rating, 156 reviews
Superhost
A well-furnished living room is depicted, featuring a dark blue couch adorned with patterned throw pillows. Two abstract art pieces hang above, and a flat-screen television is mounted on the wall. Light is provided by a table lamp, creating a bright and inviting space.
Apartment in Newport News

*Mid/Long Term Rental* Cozy Home at Mary Roberts

4.88 out of 5 average rating, 203 reviews
Guest favourite
A spacious living area is showcased, featuring comfortable seating arrangements including a dark sofa and accent chairs. Natural light is welcomed through large glass doors leading to a balcony, with views of the lush surroundings. A fireplace and modern decor enhance the warm ambience.
Apartment in Williamsburg

Cozy 2BR Condo in Williamsburg

4.92 out of 5 average rating, 90 reviews
Guest favourite
A horse-drawn carriage is seen moving along a historic street, flanked by colonial-style buildings. Gray clouds loom overhead, while bare trees line the path, adding to the scene's historical charm. The sandy road is marked with faint wheel tracks.
Apartment in Williamsburg

4BDR for you to relax & recoup in Williamsburg.

5.0 out of 5 average rating, 34 reviews

Family-friendly house rentals

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

The Williamsburg Retreat- Gorgeous Private Acreage

4.94 out of 5 average rating, 223 reviews
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

Cheerful 3-bedroom house with parking on premises

4.99 out of 5 average rating, 174 reviews
Guest favourite
Home in Williamsburg

Williamsburg Retreat

4.89 out of 5 average rating, 105 reviews
Top guest favourite
A single-story home is positioned on a grassy lot, surrounded by trees and bushes. A wooden staircase leads to the front porch, which is flanked by red shutters on the windows. The roof is gently pitched, and a clear blue sky with scattered clouds is visible above.
Home in Williamsburg

Casita on the Corner

4.97 out of 5 average rating, 281 reviews
Top guest favourite
A large, two-story white home with multiple dormer windows is set against a backdrop of lush greenery. The front features a wide staircase leading to the central door, flanked by symmetrical windows. A well-maintained lawn surrounds the house, creating an inviting exterior.
Home in Williamsburg

Spacious Home - 4 bedrooms & 3 full bathrooms.

4.95 out of 5 average rating, 125 reviews
Top guest favourite
A spacious home features a welcoming front porch with white columns and multiple arched windows. The exterior is accented by landscaped gardens and a well-maintained lawn. A carport is visible on the side, enhancing the practical design while blending harmoniously with the surrounding trees.
Home in Lanexa

Sunset Retreat *Waterfront / Spacious*

5.0 out of 5 average rating, 110 reviews
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

York River Vacation Home

4.99 out of 5 average rating, 226 reviews
Top guest favourite
A serene waterfront view showcases a gently sloping yard leading to a wooden dock. A well-maintained path lined with decorative rocks is seen, along with lush greenery and trees bordering the water's edge, inviting relaxation in a tranquil outdoor setting.
Home in Lanexa

Williamsburg Hide-A-Way Creekside

4.96 out of 5 average rating, 240 reviews

Apartment rentals with air conditioning

Superhost
A resort pool area is depicted, featuring a vibrant blue swimming pool surrounded by lounge chairs. The brick building in the background is characterized by rows of windows and a variety of green umbrellas, set against a clear blue sky.
Flat in Williamsburg

Westgate Historic Williamsburg - Westgate Historic Williamsburg One Bedroom #6

4.85 out of 5 average rating, 237 reviews
Top guest favourite
Flat in Gloucester Courthouse

Right on Main St! Shops, Arts, Dining and More!

4.96 out of 5 average rating, 149 reviews
Top guest favourite
A spacious studio apartment features a queen-size bed adorned with a colorful coral-themed quilt. Nearby, a small seating area is visible, alongside a well-equipped kitchen. Warm wood flooring enhances the inviting atmosphere, complemented by a modern ceiling fan and natural light entering through the window.
Flat in Newport News

Centrally Located Sleek Studio Apartment

4.98 out of 5 average rating, 257 reviews
Top guest favourite
Flat in North

Little Cove Cottage, Couples Retreat/Mathews

4.98 out of 5 average rating, 266 reviews
Top guest favourite
Flat in Williamsburg

Spacious 3BR Condo in Gated Community

4.95 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Yorktown

Granny Chic Suite | Full Kitchen, W/D, King Bed

5.0 out of 5 average rating, 74 reviews
Superhost
Historical reenactors are seen on a foggy morning, dressed in traditional colonial attire with three-cornered hats and red coats. Musicians play flutes, while a drummer leads the group, creating an atmosphere reminiscent of 18th-century ceremonies.
Flat in Williamsburg

Sleep 24! 8BDR/8BA Package. Multi-unit discount.

4.83 out of 5 average rating, 12 reviews
Guest favourite
A large outdoor swimming pool is surrounded by lounge areas and wooden picnic tables. Sun umbrellas in vibrant colors are positioned along the poolside. Clear blue skies create a bright backdrop, enhancing the inviting atmosphere of the resort area.
Flat in Williamsburg

Wyndham Kingsgate (3 BD LO)

5.0 out of 5 average rating, 20 reviews

Other great holiday rentals near Jamestown Settlement

Top guest favourite
Guest house in Gloucester

Cozy Fall Retreat - Creek Views & Fire Pits

5.0 out of 5 average rating, 206 reviews
Top guest favourite
The image displays The Tiny Red Barn, featuring white rocking chairs on a welcoming porch. Lush green grass surrounds the entrance, while trees create a serene woodland backdrop. To the right, a wooden dock extends into the calm waters of the Diascund Reservoir, with an American flag gently waving.
Farm stay in Lanexa

Tiny Red Barn on The Reservoir-Near Williamsburg

5.0 out of 5 average rating, 113 reviews
Top guest favourite
Guest house in Williamsburg

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

4.98 out of 5 average rating, 446 reviews
Guest favourite
A cozy living area is framed by an arched entryway, featuring a mix of seating options including a dark armchair and a spacious sofa. A coffee table made of natural wood occupies the center, while a television is mounted above a fireplace. Soft light filters through the windows.
Townhouse in Williamsburg

Cheerful 2 bedroom townhouse with fireplace

4.9 out of 5 average rating, 124 reviews
Top guest favourite
A bright cabin features an expansive wall of windows reflecting the surrounding landscape. The structure is surrounded by greenery and field, with a clear view of the water beyond. The cabin's design integrates well with the natural environment.
Cabin in Shacklefords

peaceful waterfront cabin retreat

4.97 out of 5 average rating, 298 reviews
Top guest favourite
The image showcases a row of two-story condos with light-colored exteriors set against a vibrant green lawn. Neatly trimmed bushes and small trees add to the landscape, which is touched by sunshine and soft clouds, creating an inviting environment.
Flat in Williamsburg

Historic Powhatan Resort- 2 bedroom condo!

4.91 out of 5 average rating, 317 reviews
Guest favourite
A bright and airy living space showcases large windows framing views of lush greenery. A child is seen setting up a chess board on a central table, while comfortable seating options invite relaxation in the cozy atmosphere.
Home in Spring Grove

Analog Private Beach on 10 Acres

5.0 out of 5 average rating, 34 reviews
Top guest favourite
The cottage is positioned atop a riverbank, surrounded by greenery. Stairs lead down to a sandy beach along the James River. The home’s exterior features a simple design, and the area displays a mixture of natural vegetation and the beach below.
Cottage in Surry

Riverfront Oasis | Kayaks, Private Beach, & More

4.96 out of 5 average rating, 82 reviews