A mountainous landscape with autumn foliage, rocky outcrops, and a valley below.

Find Hotels with a Pool in Middletown, VA

Check availability on Middletown Hotels with a Pool

Tonight
Oct 24 - Oct 25
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Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

Our top choices for Middletown hotels with a pool

A rectangular swimming pool with a brick wall and trees in the background.
A hotel reception desk with a blue accent, a Holiday Inn Express sign, and a coffee station.
A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.
A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a framed picture on the wall.

1. Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
Stephens City
  • Splash into seasonal fun at this rural retreat with a refreshing pool and loungers.
$83 nightly
$92 total
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG
A swimming pool with a tiled deck, chairs, and a sign indicating no lifeguard on duty.
A multi-story hotel with a prominent sign for Marriott.
A hotel lobby with a reception desk, seating area with a round table, and a bar.
A modern hotel dining area with a long table, multiple chairs, and a large window providing natural light.

2. Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
Strasburg
  • Immerse in the serene indoor pool with climate-controlled comfort after exploring Shenandoah Valley's natural beauty.
$110 nightly
$122 total
Nov 8 - Nov 9
Total with taxes and fees
Fairfield Inn & Suites Strasburg Shenandoah Valley
A pool area with a table and chairs, a turquoise umbrella, and a building in the background.
A restaurant with wooden tables and red cushioned chairs, a kitchen area with a coffee machine, and a large window.
A bathroom with a granite countertop sink, a large mirror, and a towel rack with folded towels.
A hotel room with two beds, a desk, a television, and a window with curtains.

3. Quality Inn Stephens City - Winchester South

Quality Inn Stephens City - Winchester South
Stephens City
  • Splash into serenity at this hotel's outdoor pool, where sun-soaked relaxation meets mountain country charm.
$82 nightly
$91 total
Nov 22 - Nov 23
Total with taxes and fees
Quality Inn Stephens City - Winchester South
An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.
A restaurant interior with a bar area, seating, and artwork on the walls.
A terrace with tables set for a wedding, overlooking a golf course and a body of water.

4. DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
Front Royal
  • Splash into a refreshing mountain retreat where the indoor pool meets scenic golf views.
$127 nightly
$140 total
Nov 23 - Nov 24
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows
An indoor swimming pool with clear glass walls, a tiled floor, and a view of greenery outside.
A modern indoor space with a dining area, a clock, and a view into a gym area.
A reception desk with a 'Welcome to the Mother of States' sign, a wooden panel design, and a digital kiosk.
A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.

5. Hampton Inn Front Royal

Hampton Inn Front Royal
Front Royal
  • Dive into relaxation at this mountain hotel's pristine pool, just steps from a 24-hour fitness center for active travelers.
$118 nightly
$132 total
Nov 18 - Nov 19
Total with taxes and fees
Hampton Inn Front Royal
A poolside area with lounge chairs and a stack of towels on a table.
A woman using a stationary bike in a gym with red walls and multiple exercise machines.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

6. Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
Winchester
  • Splash into a year-round swimming oasis with a refreshing indoor pool sanctuary at this Winchester hotel.
$87 nightly
$97 total
Nov 22 - Nov 23
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA
An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
A modern bathroom with a glass-enclosed shower, a vanity with a large mirror, and a built-in dishwasher.
A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.

7. La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
Winchester
  • Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.
$103 nightly
$114 total
Oct 25 - Oct 26
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
A rectangular pool with a metal ladder and a lifeguard chair, surrounded by lounge chairs and a fence.
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.
A modern bathroom with a glass-enclosed shower, a white toilet, and a vanity with a mirror and sink.
A multi-story hotel with a swimming pool, parking lot, and a landscaped area.

8. TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
Front Royal
  • Dive into seasonal splash sessions with 24-hour fitness access at this Front Royal escape.
$141 nightly
$155 total
Nov 9 - Nov 10
Total with taxes and fees
TownePlace Suites by Marriott Front Royal
A rectangular swimming pool surrounded by a wooden fence, with lounge chairs and umbrellas along the perimeter.
A hotel room with a large bed, a bathroom with a bathtub, and a framed picture on the wall.
A Baymont Inn & Suites reception desk with a blue wall, two overhead lights, and a Dell computer.
A room with two grey armchairs, a small table with a vase of flowers, a television mounted on the wall, and a desk with a computer.

9. Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
Front Royal
  • Summer bliss awaits at this refreshed hotel with seasonal pool near Shenandoah National Park.
$58 nightly
$64 total
Nov 4 - Nov 5
Total with taxes and fees
Baymont by Wyndham Front Royal Near Shenandoah National Park
A swimming pool with lounge chairs and a changing room.
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.
A bar area with a counter, multiple bar stools, and a television screen.
A hotel room with a bed, a desk with a computer, a chair, and a TV.

10. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
Winchester
  • Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.
$98 nightly
$109 total
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
View all properties

Choose what matters most at hotels with a pool in Middletown

Breakfast included
4 stars
Hot tub
5 stars
Spa

Find out more about Middletown

Discover top Middletown attractions

Middletown offers a variety of attractions that cater to adventurous travelers and families alike. For those seeking a blend of outdoor activities and cultural experiences, the beautiful parks provide ample opportunities for picnicking and leisurely strolls amidst scenic landscapes. Art enthusiasts will appreciate the local galleries showcasing vibrant works from regional artists, often accompanied by community events that invite participation and engagement. Meanwhile, history buffs can explore fascinating historical sites that reveal the town's rich heritage and stories from the past, perfect for sparking curiosity in younger travelers. If you're looking for a taste of adventure, the nearby trails offer exhilarating biking routes suitable for all skill levels, making it easy to enjoy the great outdoors. After a day of exploration, unwind at charming accommodations that prioritize guest comfort and service, ensuring a restful retreat for families and adventurers alike.

Top Middletown Hotel Reviews

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Le lit était très confortable."
Linda 1-night trip
Posted 6 hours ago
Travelodge by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"I really enjoyed the property. Extremely convenient to downtown attractions while being relatively quiet and nice. Staff was very helpful, room was lovely and clean and the pool was gorgeous."
MARY 1-night trip
Posted 6 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

8/10 Good
"Ok stay, free breakfast was good ( just there for a transit)."
Maria 1-night trip
Posted 11 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley
Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"The hotel was really well maintained inside and out! Room was super-clean."
Tammy 1-night trip
Posted 22 hours ago
Hampton Inn Front Royal
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"Very convenient at the start of skyline drive"
Ann 1-night trip
Posted 1 day ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Econo Lodge Inn & Suites Middletown - Winchester South

Econo Lodge Inn & Suites Middletown - Winchester South

10/10 Excellent
"Very nice"
Amy 1-night trip
Posted 6 days ago
Econo Lodge Inn & Suites Middletown - Winchester South

Frequently asked questions

What are some accommodations with pools in Middletown?
Wayside Inn: Offers 2 restaurants, an indoor pool, and a full-service spa. The George Washington Hotel, A Wyndham Grand Hotel: Features a health club, an indoor pool, and daily. Travelodge by Wyndham Winchester: Offers buffet, an indoor pool, and complimentary wired internet access. TRU By Hilton Winchester: Features daily, a seasonal outdoor pool, and complimentary wired internet access. La Quinta Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool, and free self parking.
What is there to see and do in Middletown?
Surround yourself with nature at Shenandoah River and Cedar Creek and Belle Grove National Historical Park. Discover sights such as Belle Grove Plantation and Jackson's Chase Golf Course during your stay. The bars, restaurants, and historic landmarks are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Middletown?
You may want to think about a place to stay that has an outdoor pool if you plan to visit Middletown in the warmest months of July, August, or June when the average temp is 72°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 36°F.

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