
House holiday rentals in Middlesex County
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Top-rated house rentals in Middlesex County
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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

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.

Waterfront Golden River Watch
Looking for a peaceful getaway on the river? Look no further than our beautiful Virginia river house. Enjoy two beautifully decorated homes, comfortable beds, and an absolutely gorgeous view of the river. Bring your boat and this will be the perfect hub. We have a ramp nearby and room on the dock to tie up your boat. Fishermen will love our dock! Or just enjoy the view and take in the quiet beauty of the Piankatank River! Perfect for trips with friends and families, retreats, or reunions.

PORT DITCHLEY - Northern Neck Waterfront Home
Enjoy the Northern Neck as you overlook the Chesapeake Bay & Pretince Creek, while relaxing on the waterfront setting of this 4 bedrm & 2.5 bathroom house. Enjoy crabbing & fishing (w your rod) on the pier; if you are arriving by boat, dock has deep water. Several adult & child kayaks & 2 paddle boards provided. Ditchley Cider Works is a 1/2 mile walk/ride House is 5 minutes from Kilmarnock. Enjoy the local wineries, restaurants, shopping, antiques, seafood, tranquility, & nature.

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

"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.

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.

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.

Cottage on Irvington
Enjoy our clean, cozy, newly remodeled 2 bedroom, 1 bath home where you can walk to downtown Kilmarnock. A coffee area and sparkling kitchen has everything you will need during your visit. The small bath has been totally remodeled to maximize the space and include a walk-in shower. Just outside the bath is a vanity area for a second person to get ready. The Cottage on Irvington is a lovely place with good light and great vibes. No smoking, no animals.

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.

Charming Waterfront Home on Piankatank River!
Amazing waterfront home on the Piankatank River in Gloucester, VA! This one level 1400sf cottage has 3 bedrooms, 2 full baths, a sun room with sweeping views, screened porch, living room with wood burning fireplace & large smart TV, fully stocked kitchen, waterside decks, a terrific fire pit, spacious dock with amazing sunsets AND sunrises, eagles overhead, kayaks and more! Want to bring your boat? There's a community boat ramp 1 minute away.

Best View on the Northern Neck, Sandy Beach!
A video tour is hosted on Youtube; please feel free to ask for the link - Airbnb won't let me include it here. You can also find it yourself on Youtube searching for the title "White Stone River Cottage". Come down the long private drive along the pasture to the little cottage perched on the banks of the river, surrounded by large oak trees. Its a simple, cozy spot with lots of outdoor spaces for spreading out.
Popular amenities for Middlesex County house rentals
House rentals with a pool

Get away to the heart of Deltaville!

Waterfront Holiday home! Kayaks, Firepit, Hot Tub

Waterfront panoramic point with pool

"The Point"-Luxury-Waterfront-Pool-Dock-Fire pit-

Rivah Getaway!

Relax in Urbanna, @ The Blue Tango!

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

Maddie's Place
Weekly house rentals

Ships Watch On The Bay With Endless Water Views

Oyster Creek Retreat: Waterfront | Dock | 2 Kings

Crab Shack

The Perfect View Virginia Tiny Home

The Guesthouse

Charming Beach Cottage on Fishing Bay

Waterfront Retreat with Office and Private Dock

Spacious | Next to Tides Inn | Stylish | Walkable
Private house rentals

Cape Cod Getaway

Eventide Inn | Peaceful, Luxury Modern w/ Hot-Tub

Serenity on the Bay | Dock | Kayak | Fish

Waterfront w/Private Pier & Firepit~Near Tides Inn

Captain's Cabin on the Creek

Weems Waterfront Getaway on Taylor Creek 🎣🚣🏻♀️🛶🌅

Willow Point Waterfront Home

Captain's Quarters
Destinations to explore
- Pet-friendly rentals Middlesex County
- Beachfront rentals Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with pools Middlesex County
- Rentals with a kayak Middlesex County
- Family-friendly rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with a fire pit Middlesex County
- Waterfront rentals Middlesex County
- Rentals with lake access Middlesex County
- House rentals Virginia
- House rentals United States
- Chesapeake Bay
- Busch Gardens Williamsburg
- Water Country USA
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Libby Hill Park
- The Poe Museum
- Colonial Williamsburg's Merchants Square
- Virginia Living History Museum
- Virginia Holocaust Museum
- The National
- Ingleside Vineyards
- Hampton University
- Virginia State Capitol-Northwest
- The Mariners' Museum
- Virginia Air & Space Sci. Center
- Sandy Bottom Nature Park
- Bluebird Gap Farm




