Pet-friendly holiday rentals in Middlesex County

The Crab Shack

Enjoy the sunrise at this unique and tranquil getaway! This property was originally a seafood processing facility...hence The Crab Shack! Watch all the action on the water right out the front door with local waterman in and out of beautiful Carter's Creek to and from the Rappahannock River and Chesapeake Bay. There are marinas and The Tides Inn very close by. This property provides privacy and a short 10 minute drive to nearby restaurants and shops in Irvington, Kilmarnock, and White Stone.

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.

Gwynns Island Waterfront Getaway

Great cottage on the water with a fantastic view of the bay and best sunset on the east coast. Sliding glass doors make it feel like your on the water when your sitting on the couch or in the kitchen. You can crab, fish, kayak, grill out and swim right off the back deck. Very peaceful and relaxing. The newly renovated island restuarant is a mile away with a bar and bascically anything you would want to eat. My father left us the house, we use all the proceeds from Airbnb to make improvements.

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.

“Old Smokey”A cozy, single bedroom, unique getaway

"Old Smokey" is a 1965 pull-behind camper that has been beautifully remodeled. It is cozy, rustic and has been restructured with lots of love. You can enjoy breathtaking sunrises and sunsets from the patio. The camper has both air conditioning and a wood stove. "Old Smokey" is a unique and romantic glamping experience. You can cook delicious meals on the grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

The Oyster House

PETS MUST BE PRE-APPROVED ($45 pet fee)! If a quiet country setting is your relaxation, this is your place. Surrounded by open fields that attract deer, turkey, osprey, ground hogs, this is natures haven. Outdoor seating around a permanent firepit or covered backporch with bar top overlooking wildlife. Renovated 2019. Yet, just seconds from downtown Deltaville. House accommodates wheelchairs. Bonus Event Room (The Spat) for 4 people available for extra cost. Ask re: price/availability.

Wooded Cabin retreat on fresh water pond

If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax. This is a pet friendly cabin.

Charming cottage next to Tides Inn with big yard

•Built in 1875, beautifully renovated •1230 sq. ft. •Level 1: Living +Family Room+Kitchen+1 Bedroom+2 Baths (no tubs) + Porch with daybed •Level 2: 1 Bedroom with daybed and 1/2 bath •Deck with views of Carter's Creek •Backyard: Large with tons of yard games & Solo fire pit •Private driveway •Steps from the Tides Inn •Minutes walk to shops, restaurants, bars in town •Free access to bikes •Small dogs permitted with host approval

Waterman's Waypoint

Waterman’s Waypoint is a newly renovated, pet friendly 3 bedroom waterfront home located on Prentice Creek. The perfect serene getaway, the property is 3 miles from the town of Kilmarnock, Virginia. There is a private dock and boat ramp perfect for personal watercraft and a deep water slip to accommodate up to a 60’ yacht. New in 2021, Adirondack Chairs, a new Fire Pit and new mattresses on the twin beds.