The Best Winchester Hotels with Pools from $94 - Hotels with indoor pools in Winchester, VA

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Our top choices for Winchester hotels with a pool

1. Microtel Inn & Suites by Wyndham Winchester

Winchester

Make a splash at this Winchester hotel with an indoor pool and fitness center for all seasons.

$87 nightly

$97 total

Aug 30 - Aug 31

Total with taxes and fees

2. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Float in style at this historic Winchester hotel featuring an elegant indoor pool and indulgent spa services.

$122 nightly

$138 total

Aug 27 - Aug 28

Total with taxes and fees

3. TRU By Hilton Winchester

Winchester

Splash into fun at this pet-friendly hotel with a pristine indoor pool and health club.

$98 nightly

$109 total

Aug 24 - Aug 25

Total with taxes and fees

Room, 2 Queen Beds, Non Smoking | Egyptian cotton sheets, premium bedding, desk, blackout drapes

4. 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

Aug 23 - Aug 24

Total with taxes and fees

5. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Splash into year-round aquatic bliss at this inviting hotel with an indoor pool paradise.

$96 nightly

$107 total

Aug 23 - Aug 24

Total with taxes and fees

Select Comfort beds, desk, laptop workspace, blackout drapes

6. Fairfield Inn & Suites by Marriott Winchester

Winchester

Splash into Winchester luxury with an indoor pool retreat in a historical Art Deco hotel.

$93 nightly

$103 total

Aug 23 - Aug 24

Total with taxes and fees

Down comforters, Select Comfort beds, desk, laptop workspace

7. Courtyard by Marriott Winchester

Winchester

Experience refreshing swims any season at this indoor pool hotel with comfy beds and onsite dining.

$107 nightly

$119 total

Aug 24 - Aug 25

Total with taxes and fees

8. Hampton Inn Winchester N/Conference Center, VA

Winchester

Splash into summer with panoramic mountain views from this seasonal outdoor pool experience.

$106 nightly

$120 total

Aug 30 - Aug 31

Total with taxes and fees

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Choose what matters most at hotels with a pool in Winchester

Breakfast included

Hot tub

Spa

4 stars

5 stars

Hotels with pools and free breakfast in Winchester

TRU By Hilton Winchester

Winchester

$98 nightly

$109 total

Aug 24 - Aug 25

Total with taxes and fees

Microtel Inn & Suites by Wyndham Winchester

Winchester

$87 nightly

$97 total

Aug 30 - Aug 31

Total with taxes and fees

The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

$122 nightly

$138 total

Aug 27 - Aug 28

Total with taxes and fees

La Quinta Inn & Suites by Wyndham Winchester

Winchester

$103 nightly

$114 total

Aug 23 - Aug 24

Total with taxes and fees

Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

$96 nightly

$107 total

Aug 23 - Aug 24

Total with taxes and fees

Fairfield Inn & Suites by Marriott Winchester

Winchester

$93 nightly

$103 total

Aug 23 - Aug 24

Total with taxes and fees

Studio, 1 King Bed, Non Smoking, Refrigerator & Microwave (Wet bar) | Premium bedding, pillowtop beds, in-room safe, desk

Hampton Inn Winchester N/Conference Center, VA

Winchester

$106 nightly

$120 total

Aug 30 - Aug 31

Total with taxes and fees

Pillowtop beds, desk, laptop workspace, blackout drapes

SpringHill Suites by Marriott Winchester

Winchester

$114 nightly

$126 total

Sep 7 - Sep 8

Total with taxes and fees

Daily cooked-to-order breakfast for a fee

Hilton Garden Inn Winchester

Winchester

$116 nightly

$132 total

Aug 24 - Aug 25

Total with taxes and fees

Standard Double Room, 2 Double Beds, Non Smoking | Blackout drapes, iron/ironing board, cribs (free)

Quality Inn Winchester

Winchester

$84 nightly

$94 total

Aug 24 - Aug 25

Total with taxes and fees

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Winchester Hotel Reviews

Quality Inn Winchester

10/10 Excellent

"The hotel is in a centric location. Denny's rest just next door."

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"All good!"

Courtyard by Marriott Winchester

10/10 Excellent

"Easy check in, nice staff, clean room, comfortable bed. I would prefer a walk in shower as I’m sure a lot of customers would"

Salamander Resort And Spa

8/10 Good

"The property and staff are amazing. Lots to do if you bring the kiddos, the kids camp let's adults relax and enjoy amenities. The one thing the property can work on is the food menu; more variety is needed. The Red Horse Tavern is a 5-minute walk into town and has the best food!! "

Frequently asked questions

What's it like visiting Winchester?

If lounging next to a pool is your idea of the perfect getaway, you may want to check out historic Winchester, which offers 7 places to stay with pools. While you're here, you can explore sights such as Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters, and then unwind poolside at one of the accommodations in Winchester that guests like for their pools.

What are some hotels with pools in Winchester?

La Quinta Inn & Suites by Wyndham Winchester: Features buffet, an indoor pool, and complimentary wired internet access. Microtel Inn & Suites by Wyndham Winchester: Offers daily, an indoor pool, and free self parking. Courtyard by Marriott Winchester: Provides a snack bar/deli, a pool, and complimentary wired internet access. Country Inn & Suites by Radisson, Winchester, VA: Features buffet, an indoor pool, and complimentary wired internet access. TownePlace Suites by Marriott Winchester: Offers a snack bar/deli, a pool, and daily.

How many hotels with pools will I find in Winchester?

Expedia has 7 hotels in Winchester for your poolside break.

What is there to see and do in Winchester?

Make a point to visit attractions like Shenandoah Valley Discovery Museum and Rocking S Ranch. During your stay, check out sights such as Stonewall Jackson's Headquarters, Patsy Cline Historic House, and Museum of the Shenandoah Valley. Winchester appeals to visitors with its array of dining options, interesting historical sites, and major shopping area.

When is the best time to book a hotel with a pool in Winchester?

You may want to think about an accommodation with an outdoor swimming pool if you will be visiting Winchester in the warmest months of July, August, or June when the average temperature is 72°F. Lodging offering an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 36°F.

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Check availability on Winchester Hotels with a Pool

Our top choices for Winchester hotels with a pool

1. Microtel Inn & Suites by Wyndham Winchester