House holiday rentals in Isle of Wight County

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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.

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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.

THE VINE—4 Bedrooms

Bring the whole family to this great place with lots of room. It boast of old world charm and character with a touch of today's conveniences. Visit Historic Downtown Franklin with shops, restaurants and the scenic Blackwater River at Barrett's Landing; all within walking distance. More restaurants & retail shops less than a mile away. Explore our beaches, botanical gardens, outlet malls, amusement & water parks within 45 mins to 1-1/2 hour drive. Lastly, have fun and enjoy. You deserve it!

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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!!

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Serene 8ac log house W/hot tub! Spacious 4BR/2BA

Welcome to your perfect short-term rental getaway in Smithfield, Virginia! Nestled along the picturesque riverbank, this enchanting log cabin invites you to unwind in the lap of natural beauty. Immerse yourself in the serenity of the surroundings as you indulge in the charm of a gorgeous retreat. **The Cabin:** Discover the allure of rustic elegance with our stunning log cabin, providing a cozy haven for your escape. You’ll be captivated by the tranquility that defines this unique dwelling.

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Magnolia Manor 4 Bedrooms , 2 Baths Cheerful house

Located on over an acre of land ,across the street from the historic James River,this 4 bedroom 2 bath home is centrally located. Christopher Newport University(CNU), Ferguson Center for the Arts, The Mariner’s Museum, James River County Club and Riverside Hospital are all approximately 1 mile away. Bush Gardens and Colonial Williamsburg are approximately 20 minutes away.This home also includes a 2 car detached garage.We cater to midterm rentals of 30 days or more with significant discounts.

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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.

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*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!

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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 shops, 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: Near the post office that starts at 4am 7 days per week. Note: Through Dec 2026 electrical utility work in the area may cause sporadic power outages.

Green Acres is the Place to Be…

Welcome to your family’s home‑away‑from‑home in beautiful Carrollton, Virginia. This bright and cozy single‑family house offers a peaceful neighborhood setting, plenty of space for kids to play, and quick access to some of Coastal Virginia’s best family attractions. You are 10 minutes away from historic downtown Smitfield (Ham Capital of the World) which features shopping and dining. Don’t forget to stop in the Isle of Wight Museum and see the World’s Oldest Edible Cured Ham.

Fully furnished Home in Newport News 10m from CNU

Take a break and get away with this newly renovated ranch style house. The house is located in central Newport News, Virginia. Having malls and shopping centers 5 to 10 minutes away you are in the middle of it all. The backyard is a prime area for family fun and gatherings. One of the bedrooms are equipped with a full sized bed and a twin trundle bed that sleeps 2. The house has 4 bedrooms allowing up to 9 guests to stay. *You must be 18 years of age or older to book*