Vacation rentals with a pool in Middlesex County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Middlesex County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Lancaster

5 out of 5 average rating, 11 reviews

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

Cottage in Urbanna

4.71 out of 5 average rating, 7 reviews

Waterfront Urbanna Home w/ Private Dock & Pool

Peaceful Setting | Dock & Boathouse w/ River Access | 1 Mi to Town | Remote-Work Friendly | EV Charger With beautiful surroundings both inside and out, this riverfront 3-bedroom, 2-bath vacation rental affords a truly idyllic retreat. Unwind in the built-in pool, opt out on the water from the private boat dock, or venture into town for sailing and oyster-sampling. Back home, relax amongst the sprawling water and forest views and enjoy modern creature comforts, courtesy of 'Heron's Hideaway.'

Superhost

Home in Lancaster

4.61 out of 5 average rating, 18 reviews

Holiday at the bay! Hot tub,water views,fire pit

Peaceful get away on the sandy shores of the Corrotoman "Rivah" full of water activities. Fast WiFi, private saltwater pool(open May-Sept), kayaks, canoe, private sand beach, hot tub, full kitchen, pool table, firepit, deck with grill, outdoor dining tables. Deep water dock bring or rent a boat. Yankee Point Marina offers boat rentals, live music & restaurant w/in walking distance! Ride free ferry into Kilmarnock for shopping, restaurants & wineries. Kayak w/dolphins, watch Rock fish from dock

Guest favorite

Home in Irvington

4.99 out of 5 average rating, 105 reviews

The Rosé Retreat: Fireplace-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

Guest favorite

Home in Locust Hill

4.97 out of 5 average rating, 115 reviews

Waterfront Cottage Getaway Pool/Kayaks/Fireplace

A timeless cottage on a private, 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.

Guest favorite

Barn in Cobbs Creek

4.95 out of 5 average rating, 111 reviews

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.

Guest favorite

Chalet in Irvington

5 out of 5 average rating, 39 reviews

Belle Chalet in the Woods

Belle is a magical chalet-style home on a wooded creekfront lot. A 5 minute walk to the center of Irvington where you can try many wonderful restaurants. A perfect setting for a romantic getaway or relaxing vacation with friends or family. Explore the many small towns of the Northern Neck by car or the surrounding area of the Rappahannock River by Kayak. The entire cottage is yours to enjoy, 3 bedrooms 3 full bathrooms, 3 outdoor living spaces! Fully equipped kitchen and high speed internet.

Guest favorite

Home in Deltaville

5 out of 5 average rating, 14 reviews

Deltaville Escape : 4BR Unwind, Relax, & Recharge

This 4 bedroom, quiet and cozy home right on the water is perfect for the off season get away or extended stay to "work from home". It can accommodate the crew for a quick fishing trip, provide a break from the fast-paced city grind, or just a cozy weekend surrounded by nature. We are all about relaxing and making memories at your own pace. So, if you’re looking for somewhere easygoing to hit “reset” for the weekend, this is it. It's comfortable, spacious and this time of year..cheap!

Guest favorite

Home in Hartfield

5 out of 5 average rating, 23 reviews

Maddie's Place

Relax with the whole family or a group of friends at this newly constructed home in Piankatank Shores, a golf cart community on the piankatank river. Plenty of space for 8 and a porta-crib available. Garage features a bar, big screen smart tv, a poker table, dart board & pool table. Relax on one of the local beaches. Plenty of parking for multiple vehicles and a boat. 12 mi to Urbanna, 1 Mi to the piakatank river golf club/steamboat restaurant. golf groups MUST BE 21 years old to book!

Guest favorite

Home in Irvington

4.99 out of 5 average rating, 122 reviews

Escape to magical wooded cottage with hot tub

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.

Home in Weems

5 out of 5 average rating, 7 reviews

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

Take it easy at this waterfront paradise in Weems, Virginia, where tranquility meets luxury. Nestled along the serene Carters Creek, this exquisite house rental offers the perfect blend of comfort, convenience, and breathtaking natural beauty. Enjoy days and nights on the private dock, the seasonal pool and the spacious home. The chef of the family will enjoy the fully stocked kitchen and multiple dining spaces! Porches galore for your morning coffee or your evening cocktails!

Guest favorite

Cottage in Irvington

4.99 out of 5 average rating, 176 reviews

Peaceful Haven: nature & 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.