Holiday rentals with a pool in Kilmarnock

Private, Riverfront Retreat, with Huge Pool

Welcome to Bali Hai! Enjoy the seclusive getaway with 5.3 acres on the Corrotoman River. Featuring botanical flower gardens along with a Koi Pond complex with 7 waterfalls. Enjoy the relaxing river views and swimming in the pool as you sip on a beverage of your choice. Sonos speakers inside and out for your enjoyment. Primary bedroom with King bed, large primary bathroom with heated floors, steam shower, and jetted tub. 15 minutes from Kilmarnock, shops, restaurants, etc.. Enjoy and relax

Waterfront Escape Pool Dock Kayaks Chesapeake Bay

Waterfront 4BR, 2.5BA cottage on Chesapeake Bay with private pool, dock, 2 kayaks a row boat, and fenced yard. Perfect for families or friends looking to relax and recharge. Enjoy cozy coastal decor, walk-in shower, claw-foot tub, full kitchen, linens, fast Wi-Fi, and smart TVs. Start your day with coffee on the dock, spend afternoons swimming or paddling, and unwind with peaceful waterfront views. Packed with amenities including games, 2 fishing rods and crab pots —your Bay escape starts here!

The Rosé Retreat: Kayaks-Screened Porch-RELAX

Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

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.

“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. 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 propane stove/grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

Wtrfrnt aptmnt w/pool/dock on private farm

Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

Magical wooded cottage pool +priv hottub walk2town

Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

Eclectic and Cozy Apartment

Close to many historical sites; Williamsburg, Yorktown, and the Northern Neck. Located on the Middle Peninsula. Close to the Tri- Rivers... fun family filled atmosphere with festivals all year long. Fully furnished. You only need your clothes and food. Full kitchen with all amenities. Owners on premises. Large dogs that are friendly. Pool available, with family and friends in and out. Small Par 3 practice space. Nice, quiet neighborhood.

Peaceful Haven: nature, pool & charming town

Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.