Holiday 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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Top guest favourite

Home in Lancaster

5 out of 5 average rating, 12 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

Superhost

Home in Lancaster

4.63 out of 5 average rating, 19 reviews

Peaceful bay retreat. 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

Top guest favourite

Home in Irvington

4.99 out of 5 average rating, 113 reviews

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

Guest favourite

Home in Deltaville

5 out of 5 average rating, 22 reviews

Deltaville Serene Riverfront Getaway | 4BR

This spacious 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, relaxation, and outdoor adventure. Wake up to stunning river views, and spend your days lounging by the private pool, kayaking, fishing, or exploring the serene surroundings. Whether you're looking for a fun-filled family vacation, or a friends' getaway, this serene stay provides unmatched tranquility Book now for spring & summer, and experience warm breezes, golden sunsets, and the ultimate waterfront experience!

Guest favourite

Barn in Cobbs Creek

4.95 out of 5 average rating, 113 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 favourite

Campervan/Motorhome in White Stone

4.89 out of 5 average rating, 118 reviews

“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 from the patio. 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 grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

Top guest favourite

Home in Irvington

5 out of 5 average rating, 43 reviews

Blue Oyster: Perfect Getaway, Pool, Kayaks, Quiet

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!

Top guest favourite

Home in Hartfield

5 out of 5 average rating, 25 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!

Cottage in Irvington

4.85 out of 5 average rating, 39 reviews

CHARMING COTTAGE, 3 AND FULL 3, KAYAK DOCK, POOL

A sunny, elegant cottage surrounded by nature is minutes from all that VA's Tidewater Region has to offer. Great eateries, boating, festivals, and upscale shopping with a small town vibe. Open plan living spaces, indoors & out, and 3 bedrooms, 3 full baths gives you room to spread out and spaces to come together. Add your kayak, miles of river, tons of games, private community pool (open memorial day) and a cool town you can walk to with great shops and restaurants and you have it all!

Top guest favourite

Home in Locust Hill

4.97 out of 5 average rating, 131 reviews

Waterfront Cottage Getaway Pool/Kayaks/Fireplace

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.

Guest favourite

Home in Irvington

4.99 out of 5 average rating, 136 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.

Superhost

Home in Lancaster

New place to stay

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!