Vacation rentals with a pool in Middlesex County

2 Waterfront Homes | Pool | Kayaks | Boats Welcome

Sunny Shores Retreat | Two Homes • Pool • Dock • Waterfront Views • Boats Welcome! Sunny Shores Retreat offers double the space with two homes on one beautiful waterfront property overlooking Meachums Creek and the Rappahannock River. Perfect for large families, fishing trips, multi-family trips, group getaways, bachelor gatherings, golf getaways and unforgettable bachelorette weekends. Sleeps up to 17 guest. This unique retreat combines room to spread out with incredible shared outdoor spaces.

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

Family waterfront vacation pool, fire pit, kayaks

Spacious home for up to 12 people dog-friendly on Corrotoman River. Enjoy a saltwater pool (May–Sept), hot tub, sand beach, kayaks, firepit, private dock for fishing, crabbing, or boating. Full kitchen with gas stove, game room, pool table, fireplace, Starlink Wi-Fi, and water-view deck. Walk to Yankee Point Marina for boat rentals, live music, and dining. Take free ferry to Kilmarnock for shopping, wineries, and entertainment. Contract & ID required. Motor boat not included. 2 security cameras

The Rosé Retreat: Pool-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

Waterfront panoramic point with pool

Peaceful, picturesque and premium waterfront property on Tabbs Creek in the Northern Neck of Virginia. Completely private 4100 square foot home on 3+ acres, yet only minutes to the charming towns of White Stone, Irvington, and Kilmarnock. Swim in the saltwater pool (May-early Oct), kayak and fish on Tabbs creek, dock your boat in the backyard and take advantage of deep water access to the Chesapeake Bay, or just enjoy the spectacular views. Comfortably sleeps 12, with 4 king size beds and 4

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.

Blue Oyster: Peaceful Getaway, Pool, Walk To Town

Welcome to the Blue Oyster at Vineyard Grove! Our unique cottage is located in the heart of Irvington, a short walk or bike ride (4 bikes for your use!) to wonderful restaurants, shopping, and 1.5 miles from the Tides Inn. Relax on the front porch to enjoy the views of the meadow, or on the screened back porch overlooking Carter's Creek. You have access to our community pool (seasonally), kayak dock (2 kayaks for your use!) & nature trails for exploring. Getaway from it all at Blue Oyster!

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.

Rappahannock Riverfront, Pool, Kayaks, Rose Garden

Escape to Rosehill Cottage — a timeless waterfront retreat on the Rappahannock River with a private pool (open mid-May), kayaks, sweeping river views, and a charming rose garden in full spring bloom. Perfect for a midweek recharge, romantic getaway, or spring family retreat. Find us on IG @rosehilllcottagerappahannock Explore nearby towns or stay close to home with open living spaces, fast WiFi, and thoughtful decor, Rosehill is your quintessential Virginia waterfront retreat.

Rivah Getaway!

“Bewdley Too” welcomes you and the family to a peaceful Rivah getaway. Enjoy the quiet country right on the Rappahanock River. Located minutes from Belle Isle State park for boat unloading. Bring your boat straight over to our pier! No boat? Kayaks and a canoe are ready for adventure. Toss in a crab pot or enjoy fishing from our pier or sit back and enjoy the pool that overlooks the river. Plenty of space for walks or yard games and get ready for some breathtaking sunsets!

Maddie's Place

Escape with family or friends to this charming golf cart community. Sleeps up to 8 guests, with a porta-crib available. Enjoy the garage game room, with three Smart TVs, a poker table, dart board, and pool table. Spend your days soaking up the sun at nearby public beaches or lounging by the private pool. - 1 mile from Piankatank River Golf Club - A short drive to Busch Gardens, colonial Williamsburg, Water country USA - 12 miles from the charming town of Urbanna