Holiday rentals in Isle of Wight County

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Top-rated holiday rentals in Isle of Wight County

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Guest favourite
A charming Craftsman house is set amidst lush greenery, showcasing a welcoming front porch with rocking chairs and a gentle sloped roof. Surrounding trees provide shade, while the warm colors of the house blend with the natural landscape.
Home in Newport News
4.92 out of 5 average rating, 229 reviews

Cozy Craftsman in Midtown

Nestled in quiet midtown Newport News, Cozy Craftsman gives new meaning to southern comfort. In addition to the queen bed in the master bedroom, a pull out couch in the den sleeps one, and in the spirit of Airbnb, another guest may bring an air mattress and bedding. CNU, Riverside Hospital, Mariners Museum, NN Shipbuilding, Jefferson Lab, military bases, and NASA are nearby as are Williamsburg, Jamestown, and Yorktown. Whatever brings you to the area, call Cozy Craftsman home during your stay!

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
4.98 out of 5 average rating, 231 reviews

Centrally Located Sleek Studio Apartment

Private guest studio apartment with separate parking/entrance in a quiet neighborhood. Centrally located to shopping, restaurants , and parks. Airport:12 min CNU:6 min Riverside Medical Center:7 min Sentara Hospital:8 min Langley AFB:11 min Patrick Henry Mall:8 min Willimasburg/Bush Gardens: approx 30 min Virgina Beach Oceanfront: 45 min Wifi available with a 55" TV with streaming services (no cable). Coffee table folds into dining/work table. Stools under table. Full bath/kitchen/laundry unit.

Top guest favourite
The entryway features a spacious living area with light-colored furniture and decorative wall art. A large area rug complements the hardwood flooring. Stairs lead to the upper level, while a small table and greenery enhance the welcoming ambiance.
Townhouse in Newport News
5 out of 5 average rating, 25 reviews

*BrandNEW*Sage & Serenity*Kng Bd

Welcome to Sage & Serenity! This unit is BRAND New with Beautiful Furnishings & Amenities Galore! All you need is your personal belongings and we've taken care of the rest! *Blazing Fast Panoramic WIFI & 2 Dedicated Workspaces *Bedroom 1: KING size bed w/Full Bath Access *Gourmet Kit w/Granite Countertops, Stainless Steel Appliances, Toaster, Rice Cooker/Steamer, Crockpot & Coffee Maker & Creamers. * Smart TVs w/Adjustable Wall Mounts for your view preference, in Each Bedroom & Living Room.

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, 299 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
Home in Smithfield
5 out of 5 average rating, 31 reviews

Downtown |Farmer Market |Fast WiFi |Easy Checkout

Welcome to the Hog Haven! Near Main Street, this house built around 1910 is a contributing structure to the Historic District. Your home is ideally situated to explore quaint shops, dine at local eateries, and immerse yourself in the town’s rich history. The Smithfield Farmers Market is a short stroll, while Windsor Castle Park is a longer walk. Note: Property is near the post office and start at 4am 7 days per week. Note: From 10/27 - 12/26 VDOT may have a small survey team on property.

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, 161 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 favourite
The exterior of a two-story colonial home is framed by large trees and a manicured lawn. White wooden siding complements the grey metal roof. A white picket fence encircles the front yard, highlighting the entrance adorned with double doors and several windows with green shutters.
Home in Smithfield
4.98 out of 5 average rating, 57 reviews

Oak Level Acres

Welcome to Oak Level! This beautiful house built in 1768 sits on 10 acres of land surrounded by over 1000 acres of farmland. Inside you'll discover unique artifacts preserved from the property's rich history. This restored colonial home sleeps 13 people comfortably with 4 bedrooms & 2.5 bathrooms. Fully stocked with fresh linens, towels, cookware, & other essentials. Only a 30min drive from Colonial Williamsburg. It is the perfect place for a family getaway, company retreat, or special event.

Top guest favourite
A charming two-story house features a covered front porch adorned with white railings and light landscaping. The exterior is painted in soft yellow, complemented by white trim. A gravel pathway leads to the entrance, with a well-maintained grassy yard on either side.
Home in Smithfield
4.91 out of 5 average rating, 216 reviews

Pigs Inn a Blanket

Pigs Inn a Blanket is the perfect spot for your Smithfield, VA stay! In close walking distance to all of the wonderful shops, farmer's market, historic spots, restaurants, parks and more. After you have toured all the wonderful things Smithfield has to offer, enjoy time with your family in the backyard oasis, with the grill and/or the fire pit. The home features 3 bedrooms and 2 full baths with a living room, dining area, kitchen and laundry. Perfect spot for you and your family! NO SMOKING!!

Top guest favourite
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 favourite
Home in Suffolk
4.92 out of 5 average rating, 13 reviews

Nix Cove Haven

Clean, comfy, private room with a queen bed and entire ground floor in a safe and quiet neighborhood. Enjoy the privacy & comfort of your own space with everything you need to relax after a long day: bedroom with TV, private bathroom, high speed WiFi, coffee bar, fridge, microwave & the added convenience of a washer/dryer. All the modern conveniences of home with the feel of a cabin in the woods. Cozy up and watch a movie by the electric fireplace inside or relax on the deck by the water.

Top guest favourite
A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.
Home in Suffolk
4.85 out of 5 average rating, 107 reviews

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

Top guest favourite
The barn loft is illuminated under the night sky, highlighting its rustic red exterior and decorative features. The front displays large garage doors, flanked by well-maintained landscaping and outdoor lighting. A weathervane sits atop the roof, while an American flag adds a touch of charm to the entrance.
Barn in Suffolk
5 out of 5 average rating, 22 reviews

Cozy Waterfront Barn Loft

Rustic Charm Meets Modern Comfort in Our Barn Loft Retreat Welcome to our beautifully converted hay loft, a serene escape nestled on a former horse farm along the picturesque Chuckatuck Creek. This rustic yet modern loft offers the perfect combination of charm and convenience, making it ideal for family getaways (sleeps up to 8 with pullouts), work trips, wedding weekends, or a peaceful retreat to recharge your soul.

Popular amenities for Isle of Wight County holiday rentals