Waterfront holiday rentals in Middlesex County

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

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.

Creek cottage getaway

House address is 520 Paynes Creek rd. Down sandy road house is to the left. Last house on road. Comfortable cottage on Paynes creek going out to Rappahannock River. 1 bedroom with queen sized bed and sofa that folds out to a full sized bed in the living room. House has high speed fiber internet. There is a dock with crab pots to use. Crab season Is May 15 - Nov 15. No crabs outside of those dates. Please do not use boat. It leaks. It's not safe. 7812 River road is laundromat. Use front door.

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.

Waterfront Guesthouse I on the Rappahannock

The “Bay House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has a beautiful Bay view and includes access to our private beach & dock (w/ guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath w/ jetted tub, covered patio and carport. The 2nd floor features a large bedroom, king bed and 1/2 bath.

Gwynns Island Waterfront Getaway

A lovely waterfront cottage with stunning bay views and the best sunsets on the East Coast. Sliding glass doors create the feeling of being right on the water, even when indoors. You can crab, fish, kayak, grill, and swim directly from the backyard. It's incredibly peaceful and relaxing. Just a mile away is a newly renovated island restaurant with a bar and a wide variety of food options. The house was passed down from my father, and all proceeds from Airbnb go towards making improvements.

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Cottage on Prentice Creek, PA

Cozy two Bedroom Cottage with a Sectional Sofa that has queen bed pull out. Screened Porch, Large Patio & Dock to enjoy views of the creek and wildlife. Great for a romantic getaway or vacation. Well-appointed kitchen. Dogs allowed (2 Max, under 70 pounds-must be notified first) an additional fee of $60 per dog. No third-party bookings. Just outside Kilmarnock, very close to White Stone and Irvington with a good variety of Restaurants, Wineries, Breweries a Cidery and shopping.

The Rudder. Great Views!

Cozy warm cabin! Large kitchen with eating area, bath with tub/shower, bedroom with queen bed, family room with a queen pull out sofa and a separate bedroom with 2 twin beds. Large screened in porch with wonderful views of the Bay. This property is located in Cross Rip campground. Guests of the cabin have access to the beach and pier. This cabin also has an adjoining cabin (like at a hotel) that will sleep an additional 4. Please see our listing for The Stateroom. NO PETS.

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 50’ yacht. New in 2026, Level 2 Universal EV Charger with Tesla charging adaptor. New in 2024, Front porch upgrade. New screens and door.

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Welcome to 'The Pearly Oyster,' your ideal waterfront retreat! This 3-bedroom, 2-bathroom cottage sleeps 8 and offers stunning river views, a fully equipped kitchen, and unique decor. Enjoy grilling on the deck, family-friendly amenities, and paddle the Corrottoman from our private dock. Explore nearby Kilmarnock, Irvington, and White Stone with access to local playgrounds, tennis and pickleball courts. Be our guest!