Holiday rentals in Wakefield

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Top-rated holiday rentals in Wakefield

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Top guest favourite
The dining area features a wooden table surrounded by metal chairs, set near a sliding glass door leading to a deck. A centerpiece of purple flowers adds a touch of color. Modern light fixtures hang above, providing ample illumination.
Home in Charles City
4.98 out of 5 average rating, 116 reviews

Cap 2 Cap Cottage VA Capital Trail Charles City

Cap 2 Cap Cottage - Rural oasis awaits in a NEWLY RENOVATED COTTAGE on 6 acres. 52 mile Virginia Capital Trail (Jamestown - Richmond) is only 3/10 of a mile away.Primary suite w/ 1 King bed. Add'l bedroom w/ 1 Queen bed. 2 full baths. Great Wifi, Smart TV, fully equipped kitchen, private deck. Fantastic restaurant/brewery Indian Fields Tavern is 3 miles away. Perfect stay for cyclists ,history lovers or just unwinding. NO Smoking or parties. Colonial Williamsburg 24 miles, Richmond is 30 miles .

Top guest favourite
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, 291 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 favourite
A cozy living area is presented with a light-colored sofa adorned with yellow cushions. Nearby, a dining table with wooden chairs is set against the wall. A functional kitchen area features teal cabinetry and stainless steel appliances, illuminated by soft overhead lighting.
Flat in Chester
4.96 out of 5 average rating, 27 reviews

Green Door Escape

Forget your worries in this spacious and serene space. Enjoy a comfortable stay with a private entrance, separate from the main house, with parking at your front door. Privacy prevails! A comfortable home away from home. Access to a lush garden. Queen bed, private en-suite bathroom with shower. Fitted kitchen: Induction-stove ( two plate), Air-fry Microwave, Coffee maker, and Refrigerator. Crockery, cutlery, cookware and utensils, provided. Basic cleaning supplies. Linen changed weekly.

Top guest favourite
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, 156 reviews

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.

Superhost
In the backyard, a vibrant croquet set is displayed on lush green grass, with a red ball positioned near a hoop. In the background, swings hang from a frame, bordered by a wooden fence and shaded by tall trees.
Home in Spring Grove
4.9 out of 5 average rating, 31 reviews

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, Tubelox, 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!

Top guest favourite
Home in Williamsburg
5 out of 5 average rating, 121 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, antiques, 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.

Top guest favourite
A cozy red bungalow is enclosed by a wooden fence, with a welcoming front porch. Adjoining seating includes blue and white adirondack chairs, offering a relaxing outdoor space. Clear skies and distant farmland create a peaceful backdrop for this private retreat.
Cabin in Wakefield
4.94 out of 5 average rating, 63 reviews

Sugarshack

Want to getaway and enjoy the sounds of nature. My unique bungalow is on my beautiful farm in quiet Surry County located just outside Wakefield. But still minutes from the free Scotland ferry to Williamsburg and the industry here. This is a great valued stopover. Perfect for 2 romantic folks, or a close family member or a working person who just happens to be working here. We also have WiFi and a smart tv that’s perfect. Plus a very clean bathroom, shower and wash station very close by.

Top guest favourite
A calm pond reflects the surrounding trees under a clear blue sky. Lush greenery frames the water's edge, enhancing the serene landscape. The stillness of the water mirrors the tranquility of the environment, inviting relaxation and connection with nature.
Farm stay in Yale
5 out of 5 average rating, 33 reviews

Rustic farmhouse-80 acres-Pond

Our newly renovated farmhouse that sits on 80 acres of land, overlooking two ponds that are fully stocked with fish for fishing. Our two story, open concept, house provides ample space for up to 9 people . Enjoy the downstairs with two living rooms, a full kitchen and two full bathrooms. The downstairs has two bedrooms (3 beds). The upstairs of the house is only opened when more than 5 guests are booked (additional fees apply). The upstairs has 2 additional bedrooms and a half bath.

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
4.84 out of 5 average rating, 469 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 favourite
A spacious bed, adorned with crisp white linens and decorative pillows, occupies the center of the room. A wooden headboard adds warmth, while a bedside lamp offers soft lighting. Natural light filters through a large window, framed by patterned curtains.
Flat in Williamsburg
5 out of 5 average rating, 7 reviews

Chic Urban Living: 1BR in Kingsgate!

Furnished in the Colonial style, this resort offers all the modern amenities and activities you could want. Surrounded by the area's top attractions and historic landmarks, there's plenty to explore, ensuring that your getaway is one to remember. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $250 refundable security deposit on hold at resort check-in. . Resort Fee at $7 per night. • Name on reservation must match photo ID at check-in.

Top guest favourite
An aerial view captures the riverfront A-Frame home surrounded by lush greenery. The spacious deck extends toward the water, showcasing a blend of natural beauty and modern architecture under a soft, early evening sky.
Home in Charles City
4.99 out of 5 average rating, 311 reviews

Hutch's Bluff - Waterfront near Williamsburg

Charming riverfront A-Frame home on 2 acres overlooking the Chickahominy River. Completely updated interior, including all furnishings and appliances. Wake in a King bed loft space with a majestic view of the river, or choose one of the two Queen bedrooms below. First floor all tile bathroom with a walk in shower. Stainless appliances and granite countertops. Bring your fishing gear, relax at the end of the pier, or enjoy the views from the large deck and fire pit.

Guest favourite
A two-story garage features a sloped roof and a set of double windows on the upper level. A concrete driveway extends beside it, flanked by greenery and a seating area. Sunlight illuminates the space, enhancing its inviting appearance.
Guest house in Chesapeake
4.88 out of 5 average rating, 86 reviews

Western Branch Loft Suite

Enjoy your own space in this quiet studio located near Navy bases, hospitals, and the beach. It’s perfect for those looking for a little bit of peace while they are in the area for work, house hunting, visiting family or friends. This comfy guesthouse is in a safe neighborhood 5 minutes from grocery stores, restaurants, gyms, and highways to get around. Avoid the busiest traffic areas here while still being able to enjoy a day trip to the beach!

Popular amenities for Wakefield holiday rentals

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  2. United States
  3. Virginia
  4. Sussex County
  5. Wakefield