Pet-friendly holiday rentals in Isle of Wight County

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.

Walkability · Outdoor spaces · Family

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.

Pets · Outdoor spaces · Sleep quality

The CrackerJack House: A Military Salute & Arcade!

There is something for everyone at this house! Spacious, stylish & comfortable with the added fun of a free home arcade! Leave your quarters at home! The house is themed with authentic & antique military photos & memorabilia, a special salute to all the men & women in the military! Home includes a Jukebox & Outdoor Pool Table, picnic area with gas grill & fire pit with ring of chairs perfect for stargazing. Equipped with BONUS FREE ARCADE ROOM! Air Hockey, Foosball, dart board & more! Come play!

Pets · Outdoor spaces · Checkout

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.

Outdoor spaces · Pets · Sleep quality

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.

Outdoor spaces · Pets · Comfort

*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!

Pets · Indoor spaces · Getting around

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.

Walkability · Pets · Location

𓂃Tidal Creek Retreat: Near CNU, JLab and Busch𓂃

Relax at this serene & unique water getaway! 🏞️ This cozy two-story home on a cul-de-sac is ideal for nature lovers & wildlife spotting. Enjoy the panoramic tidal creek views from chef's kitchen or play board games by the gas fireplace. Need to work? A cute desk, extra monitor, & ergonomic chair are waiting for your next project. With a full dining room, luxurious body jet/rainfall showers, pool + outdoor hot tub, it's a great spot for family reunions or unwinding after a busy day!

Outdoor spaces · Pets · Bathroom

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.

Pets · Beach · Check-in

The Quiet Escape | Family Retreat

Stay in the heart of Hampton Roads in a safe and quiet neighborhood. VA Living Museum ~8 minutes Patrick Henry Mall ~15 minutes Newport News Park ~20 minutes Busch Gardens ~30 minutes Water Country USA ~30 minutes City Center ~5 minutes Port Warwick ~8 minutes Yorktown Beach ~25 minutes CNU ~6 minutes Hampton University ~20 minutes William & Mary ~25 minutes Langley Air Force Base ~15 minutes Fort Eustis Military Base ~20 minutes Naval Weapons Station ~20 minutes

Pets · Bathroom · Family

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!

Outdoor spaces · Walkability · Hospitality

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.

Walkability · Outdoor spaces · Beach