Vacation rentals in Wakefield

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Top-rated vacation rentals in Wakefield

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Top guest favorite
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, 176 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 favorite
A well-appointed bedroom features a spacious bed with a textured white cover. Colorful accent pillows add depth to the decor. A wooden dresser stands against one wall, while a bedside lamp illuminates the space. Natural light filters through a window adorned with light curtains.
Home in Smithfield
4.97 out of 5 average rating, 295 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Top guest favorite
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.
Guesthouse in Gloucester County
4.98 out of 5 average rating, 202 reviews

Modern Cabin w/ Hot Tub, Fire Pit, Creekside 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 favorite
A serene cottage, surrounded by lush greenery, features a welcoming front porch with chairs and warm lighting. A gravel pathway leads to the entrance, highlighting the harmony between the home and its natural surroundings.
Farm stay in Smithfield
5 out of 5 average rating, 158 reviews

Cozy Farm Cottage with Horses, Fire Pit, & Trails

Escape to Timberline Ranch, a 30-acre horse farm near historic Smithfield. Horses and goats are visible from multiple windows. Your bedroom is cozy with room-darkening drapes, plenty of blankets and pillows. The kitchen is well stocked. Coffee station stocked and to-go cups. Bathroom has a ceiling heater, towel warmer, essentials. W/D with detergent. Step out to the front porch rocking chairs, fire pit (wood incl), and picnic table. Explore trails, follow the creek, and hunt for hidden gnomes.

Top guest favorite
A circular fire pit is surrounded by stone blocks, with logs burning brightly in the center. Smoke gently rises into the air, and the area is bordered by grass and a quiet wooded backdrop.
Home in Surry
4.98 out of 5 average rating, 115 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.

Guest favorite
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.
Apartment in Williamsburg
4.84 out of 5 average rating, 479 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.

Top guest favorite
A wooden deck offers a comfortable outdoor space, featuring two rocking chairs with floral cushions. A small table stands neatly between them, adorned with a vase of flowers. Surrounding trees showcase autumn foliage, creating a serene backdrop.
Cabin in Dinwiddie
5 out of 5 average rating, 112 reviews

Dinwiddie Couples Getaway- Wells Cabin @WeldanPond

Wells Cabin @Weldan Pond is a beautiful new space designed for couples who love to relax, enjoy the outdoors (hike, fish, trail bike, & more), & marvel over beautiful views. The Cottage has a full kitchen, a large king bedroom, a bright, window filled sitting area, and a new deck overlooking Upper Weldan Pond and acres of healthy, natural hardwood forest with nearly 4 miles of trails to explore. You'll also love just enjoying the deck and the beauty of the Virginia countryside.

Top guest favorite
A vibrant sunset paints the sky in shades of orange and pink, casting reflections on the water. Silhouettes of a dock and surrounding trees create a serene waterfront scene, highlighting the natural beauty of the location.
Home in North
4.99 out of 5 average rating, 107 reviews

The Llama House

Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.

Top guest favorite
Guesthouse in Williamsburg
4.98 out of 5 average rating, 407 reviews

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

The Freedom Cottage is a charming little cottage comfortable for four, can fit 5 with the sofa bed. You're minutes away from Freedom Park, The Premium Outlets, Jamestown Settlement and 15 minutes from Colonial Williamsburg, Busch Gardens and Water Country. The Williamsburg Winery is also well within reach of our home! Our place offers maximum utility and privacy! We ensure to sanitize every surface, wash every towel and replace every sheet after each guest.

Top guest favorite
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, 388 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 favorite
A cozy bedroom features a spacious bed adorned with a floral quilt. Nightstands with lamps sit on either side, offering soft lighting. Artwork in warm tones is displayed on the walls, complemented by a vintage mirror above the headboard. A comfortable seating area is visible in one corner.
Farm stay in Toano
4.95 out of 5 average rating, 312 reviews

Farm Stay - Guest Suite w/ Private Entrance

Ready to add some adventure (and a few new animal friends) to your Williamsburg trip? Stay at our cozy little homestead, where the coffee’s hot and the chickens are nosey. Watch amazing sunrises, sunsets and starry skies that’ll make you forget about city life. We also have goats and a couple of obnoxious geese to meet (if you want). Slow down, savor the countryside, and reconnect all while being only 15 minutes from Williamsburg.

Top guest favorite
An aerial view depicts the guest suite, nestled among lush greenery, with a spacious swimming pool nearby. The main house, along with various outdoor amenities, is visible, showcasing well-maintained landscaping and open fields surrounding the property.
Guesthouse in Suffolk
4.97 out of 5 average rating, 159 reviews

Country Living Guest House (Upstairs/Downstairs)

This country living guest suite is conveniently positioned on Lone Star Lakes Park. It is located in a quiet, private drive. Prepare quality meals in the down-stairs fully equipped eat-in kitchen with built-in cabinets, spacious countertops, a full-sized fridge, an electric stove, and everything you need to feel at home. Just off the kitchen is a half-bath. NO PETS ALLOWED.

Popular amenities for Wakefield vacation rentals

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  4. Sussex County
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