Vacation rentals with a kayak in Middlesex County

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

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

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.

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.

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.

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.

Coastal Farmhouse Getaway

Take it easy at this unique and tranquil getaway. This fully renovated historic farmhouse sits on 4 acres on Windmill Point. Spend the day on the expansive yard or our private beach on the Rappahannock/Chesapeake Bay. Perfect for fishing, crabbing, kayaking or just relaxing! The waterfront pavilions and tiki bar are the perfect oasis to set up camp. The house was completely renovated historic home that offers unmatched comfort and charm. Enjoy water views from almost every room!

"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.

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

The Oyster House

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.

Creeks End Farmhouse

At the end of a country lane, on the banks of Henry's Creek off the Chesapeake Bay and near the village of Kilmarnock, Virginia sits Creeks End Farmhouse. This charming home built in 1903 was once a working farmhouse, but now welcomes family and friends to come relax and play. Enjoy crabbing or fishing from the dock, paddling the creek out to the bay, lazing in the adirondack chairs on the wrap around deck, or napping on the screened-in porch.