The Best Middletown Hotels with Pools from $36 - Hotels with indoor pools in Middletown, VA

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

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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 breakfast area with seating, a counter for hot food, and a view of the outdoors.

A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.

1. 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.

$32 nightly

$36 total

Nov 21 - Nov 22

Total with taxes and fees

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

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

A pool area with a table and chairs, a turquoise umbrella, and a building in the background.

A reception area with a marble counter, a desk, and a framed picture on the wall.

A hotel room with two beds, a desk, a television, and a window with curtains.

A restaurant with wooden tables and red cushioned chairs, a kitchen area with a coffee machine, and a large window.

3. 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

An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

A restaurant interior with a bar area, seating, and artwork on the walls.

A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

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

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

An indoor swimming pool with clear glass walls, a tiled floor, and a view of greenery outside.

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.

A gym with a rack of dumbbells, kettlebells, and exercise balls.

5. 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

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

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

An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.

A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

7. 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

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 multi-story hotel with a swimming pool, parking lot, and a landscaped area.

A conference room with a large table and chairs, a TV mounted on the wall, and a vending machine labeled "Towneplace Suites".

8. 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

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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

Spark by Hilton Winchester

10/10 Excellent

"Clean room, great staff, good parking and free breakfast"

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

10/10 Excellent

"Everything was clean and br.eakfast was adequate for traveling and buffet style. Staff was very friendly and helpful. There was no problem with parking. Do be aware that it is just off Interstate 81 and you can hear (although just barely) trucks during the night. It wasn't a problem for us."

Hampton Inn Front Royal

10/10 Excellent

"The hotel was really well maintained inside and out! Room was super-clean."

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Super clean, very quiet and excellent breakfast. Highly recommend."

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"It was close to everything."

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent

"Very convenient at the start of skyline drive"

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"rooms are clean, spacious, and serviced everyday. Good breakfast on offer and the Bar is good too. Greal location and good parking. Staff very helpful and knowledgeable about the area. Shenandoah mountains are wonderful. Lots of wineries and farmers market near by"

Econo Lodge Inn & Suites Middletown - Winchester South

10/10 Excellent

"Very nice"

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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Check availability on Middletown Hotels with a Pool

Our top choices for Middletown hotels with a pool

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

2. Fairfield Inn & Suites Strasburg Shenandoah Valley

3. Quality Inn Stephens City - Winchester South