
Holiday houses in Isle of Wight County
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Top-rated holiday rentals in Isle of Wight County
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1-Bedroom Home Near Christopher Newport University
Sip a bourbon while you listen to a record on the vintage player. Create your CD playlist to pop in the 90s 5 disk changer while you cook on a seasoned cast iron on the new stove. Check out the coffee bar for home roasted beans. Soak in the hot tub, or get a high score on Dig Dug. Centrally located in Newport News near CNU. 25-30 minute drive to Busch Gardens, Water Country, and Colonial Williamsburg. 45 minute drive to the ocean front. Great neighborhood with sidewalks for running and walking.

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.

*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.

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.

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.

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.

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.

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!!

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.

*NEW* Cozy & Very Stylish home for your family!
Enjoy your time with family or as a solo traveler in a stylish & spacious home with over 2100 sq ft! Just mins from Riverside hospital and CNU, 15 mins from beaches, 35 mins from VA beach, and 17-20 minutes from Busch Gardens & Colonial Williamsburg in a "PERFECT" location in the heart of Hampton Roads, located in a safe, quiet, and beautiful neighborhood. This home offers the perfect blend of comfort, style, convenience, and charm—ideal for families, medical staff, or all vacationers alike!

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!

The Harlequin Cottage
This unique place has a style all its own. Cottages on the Point was launched in 2018 and offers timeless interior styling and stunning resort style outdoor views. The property features a seasonal (Mid-April to the end of October) 14,000 SF outdoor tiki bar with a shared saltwater pool with swim up bar, outdoor kitchen, and live music. The residences are adjacent to the tiki bar deck and include open layouts, terraces, and custom décor.
Popular amenities for Isle of Wight County holiday rentals
Other great holiday rentals in Isle of Wight County

Shalom

Cozy Luxe Stay:Patio, Pool Table

Country living in the City

Newport News 4BR | Saltwater Pool & View

Relax at the Captains Quarters!

Relax in this Tree Oasis.

Three bedroom Townhouse

Relax & Recharge. Simple, clean, stress-free stay.
Destinations to explore
- Apartment rentals Isle of Wight County
- Rentals with pools Isle of Wight County
- Pet-friendly rentals Isle of Wight County
- Rentals with a fireplace Isle of Wight County
- Rentals with outdoor seating Isle of Wight County
- Rentals with a fire pit Isle of Wight County
- Family-friendly rentals Isle of Wight County
- House rentals Isle of Wight County
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Water Country USA
- Buckroe Beach
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Town Point Park
- Old Dominion University
- Hampton University
- Virginia Living History Museum
- First Landing Beach
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Regent University
- The Mariners' Museum




