Pet-friendly holiday rentals in Gloucester County

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

Escape to your charming and spacious home in the heart of Mathews. Perfect for families, groups, and couples—including 4-legged friends! The home offers the ultimate blend of comfort and small-town tranquility. Thoughtfully updated spaces, large backyard, and prime location, you'll feel right at home. The ideal base for your Chesapeake Bay vacay, your house is just a stone's throw from the best restaurants and shops, and a quick drive to beautiful beaches. Book today and start making memories!

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Nan's Place aka Down Easter

This cabin is very Unique. The front portion of the cabin is a wheel house off of an old Steam boat. The twin bed is in this part of the wheel house. This cabin has a great water view with a large deck and a screened in porch. It has a full bath. The main living area is basically a studio with a queen bed, full size fridg, micro, toaster oven, stove, kitchen sink, keurig, charcoal bbg grill. This is a dog friendly (no cats, sorry) cabin and is located in a small campground called Cross Rip.

The Cottage at Elm Bank

Adorable 2-bdrm, 2-bath cottage on the grounds of Elm Bank, an 8-acre waterfront estate overlooking the Piankatank River and Ferry Creek. Enjoy fishing on the pier, kayaking from the beach, birdwatching from the deck, working out in the gym or playing pickleball on the newly installed court. The property sits on a peninsula known as Piney Point, a welcoming neighborhood with a community dock and boat ramp. Come relax in a park-like setting. You'll find everything you need, nothing you don't.

Stunning Beachfront Cottage on the Chesapeake

Take a break and unwind at this peaceful oasis. Near the end of a private road, enjoy direct beachfront access to the entrance of the Chesapeake Bay. Chill on your own sandy beach, wade in the water, and watch an endless display of boats at quiet Stingray Point. A private lighted pier, outdoor shower, and river room porch will make your stay worthwhile. With four bedrooms (one has bunk beds and a foosball table and is accessed through the third bedroom) you'll have all the room you need.

Million $ Views! Pool! Private Hot Tub! EV Charger

Welcome to The Cottage at Misti Cove, where the Piankatank River is just steps from your door. Wake to sunrise views from bed, paddle the river by kayak or paddleboard, and unwind in your private waterfront hot tub as evening settles over the water. Enjoy the peaceful setting of a small community along with a seasonal pool, beach, pier and tennis court. It’s a cozy waterfront escape with exceptional views, thoughtful comforts and plenty of ways to slow down and say, “Now this is the life.”

Serenity Farm Equestrian Retreat in Historic VA

Relaxation at its finest for up to 16 guests at Serenity Farm in historic Gloucester County, VA. We are a working barn that overlooks groomed pastures and luscious gardens while offering views of a private equestrian estate. You will have full private access to this beautifully decorated farmhouse while enjoying the views, amenities, and proximity to history, golf, shopping, and theme parks! Historic Museums, Shopping, Restaurants, Local Breweries, and Art Galleries are only minutes away!

Spring is a great time in Gloucester!

Enjoy a peaceful get away at this home in historic Gloucester, Va. This upscale home is located between two creeks that feed into the Piankatank River. It is not waterfront. It is centrally located to Mathews, Gloucester, Urbanna and Gwynns Island. Williamsburg is about a 50 minute drive. This part of Virginia is known for fishing, water sports, beaches and history. Come stay in this newly renovated rancher and enjoy the country on the river. We welcome one small dog under 50 lbs.

Historic Ware River Cottage at Glebefield

Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.

The Bee Goode House on Main Street

Welcome to the Bee Goode House! We want our future and returning guests to know of our diligence in sanitizing and cleaning every surface after each guest. Linens are fresh and clean, and there is plenty of private space with a large yard surrounding the house. Relax and enjoy Gloucester Main Street from a 1950's renovated home. From Mid Century Modern furniture and renovated retro appliances, you will be comfortable and hip in our home.

Bamboo Bungalo Duplex Near Busch Gardens

Find your home away from home when visiting historic Williamsburg. It feels very private here nestled amongst the bamboo and trees. This is a great location for families with children! We are within 5 minutes of Bush Gardens and Water Country for great family fun outings! For history buffs, we are 7 minutes from Colonial Williamsburg, 15 minutes from Jamestown Settlement and 20 minutes from Yorktown Battlefields.

Casita on the Corner

The Casita is a cozy 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens-Water Country. The area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. There is a shopping center with a Grocery store and restaurants within walking distance from the property.