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

Find Hotels with a Pool in Middletown, VA

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Check availability on Middletown Hotels with a Pool

Tonight
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Middletown hotels with a pool

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.

1. 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.
$101 nightly
$113 total
Nov 8 - Nov 9
Total with taxes and fees
Fairfield Inn & Suites Strasburg Shenandoah Valley
A rectangular swimming pool with a brick wall and trees in the background.
A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a framed picture on the wall.
A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.
A hotel reception desk with a blue accent, a Holiday Inn Express sign, and a coffee station.

2. 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 pool area with a table and chairs, a turquoise umbrella, and a building in the background.
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.
A bathroom with a granite countertop sink, a large mirror, and a towel rack with folded towels.

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 restaurant interior with a bar area, seating, and artwork on the walls.
A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.
A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

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
$141 total
Nov 11 - Nov 12
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows
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 Country Inn & Suites by Radisson building with a covered entrance and multiple windows.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

5. 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
A large indoor swimming pool with clear blue water, surrounded by walls with large windows offering views of greenery.
Room
Bathroom
A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.

6. 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 19 - Nov 20
Total with taxes and fees
Hampton Inn Front Royal
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

La Quinta Inn & Suites by Wyndham Winchester
Winchester
  • Dive into the inviting indoor pool, perfect for year-round swims at this clean, modern hotel.
$107 nightly
$119 total
Oct 27 - Oct 28
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.
A conference room with a large table and chairs, a TV mounted on the wall, and a vending machine labeled "Towneplace Suites".
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 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.
A Baymont Inn & Suites reception desk with a blue wall, two overhead lights, and a Dell 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 hotel room with a bed, a desk with a computer, a chair, and a TV.
A bar area with a counter, multiple bar stools, and a television screen.
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

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

Top Middletown Hotel Reviews

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Front desk upgraded our room so we could fit our bikes in the room. Bed was too soft. Otherwise room was nice. Breakfast was good."
Jenny 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Winchester, VA
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

8/10 Good
"Room was clean and quiet.. Breakfast was sufficient."
David 1-night trip
Posted 4 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Great room, attentive staff, breakfast hit all the notes"
Ciro 1-night trip
Posted 18 hours ago
Fairfield Inn & Suites by Marriott Winchester
The George Washington Hotel, A Wyndham Grand Hotel

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"
Owen 5-night trip
Posted 22 hours ago
The George Washington Hotel, A Wyndham Grand Hotel
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Clean friendly"
Lesley 3-night trip
Posted 1 day ago
Travelodge by Wyndham Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"What a pleasure staying a night in such a new, sparkling clean hotel! Location was fantastic with lots of stores and restaurants and the Highway very close! Our room was extremely clean and comfy! The front desk clerk on the night of Oct 18 was fantastic and friendly! Breakfast was just Continental, but better than nothing!"
Tina 1-night trip
Posted 3 days ago
Spark by Hilton Winchester

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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