Find Hotels with a Pool in Winchester, VA

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Pick from 27 Winchester Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Exterior
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4 out of 10, Exceptional, (1004)
"Beautiful town. The hotel is beautiful. "
The price is SAR 469
SAR 532 total
includes taxes & fees
27 Jum. I - 28 Jum. I
The George Washington Hotel, A Wyndham Grand Hotel
Exterior
Spark by Hilton Winchester
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Great"
The price is SAR 329
SAR 372 total
includes taxes & fees
24 Jum. II - 25 Jum. II
Spark by Hilton Winchester
Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1345)
"Dog friendly and very convenient to I-81 on/off ramp."
The price is SAR 402
SAR 437 total
includes taxes & fees
26 Jum. I - 27 Jum. I
La Quinta Inn & Suites by Wyndham Winchester
Exterior
DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
9.0 out of 10, Wonderful, (1001)
"Free cookies😊"
The price is SAR 443
SAR 500 total
includes taxes & fees
9 Jum. II - 10 Jum. II
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Exterior
Hilton Garden Inn Winchester
3.0 star property
9.0 out of 10, Wonderful, (425)
"Everything was great except for the desk attendant who did not understand much english and had to continue to go get someone to help answer questions which made it inconvenient. Beyond that it was a great stay at a good property"
The price is SAR 514
SAR 583 total
includes taxes & fees
1 Jum. II - 2 Jum. II
Hilton Garden Inn Winchester
Pool
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (1001)
"The staff and room was superb. "
The price is SAR 452
SAR 503 total
includes taxes & fees
24 Jum. II - 25 Jum. II
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
Exterior
Fairfield Inn & Suites Strasburg Shenandoah Valley
2.5 star property
9.0 out of 10, Wonderful, (1000)
"Very friendly staff and free breakfast"
The price is SAR 461
SAR 513 total
includes taxes & fees
5 Jum. II - 6 Jum. II
Fairfield Inn & Suites Strasburg Shenandoah Valley
Japanese garden
Holiday Inn Express Hotel & Suites Winchester, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, (671)
"Fantastic check in, lady at front desk was very fast and kind to my two daughters. She gave each give piece of fruit at check in and daughters got chocolate chip cookies a little bit later. Nice clean room! In a good location , lots of quick foods within two minutes. Indoor pool and hot tub were a hit with the girls. A small workout room also. Only two downfalls -fire alarms went off at 4am had to evacuate, it was in sprinkle system was told, and the breakfast was a little cool. All in all...
The price is SAR 521
SAR 567 total
includes taxes & fees
24 Jum. II - 25 Jum. II
Holiday Inn Express Hotel & Suites Winchester, an IHG Hotel
Exterior
Hampton Inn Front Royal
2.5 star property
8.8 out of 10, Excellent, (1002)
"Well kept, friendly stay. The bed was a bit more firm than I care for but this is a clean, well run hotel where guests are comfortable hanging out in the well appointed lobby/dining area. Coffee, tea & hot chocolate always available."
The price is SAR 458
SAR 509 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Hampton Inn Front Royal
Exterior
Quality Inn
2.5 star property
8.8 out of 10, Excellent, (999)
"We were in for our son's graduation. This place is a nice place to stay and conveniently located. It is not an upscale high dollar hotel but we didnt need that. It met our needs. The staff is great. Our room was clean and the breakfast selectio was great"
The price is SAR 347
SAR 378 total
includes taxes & fees
9 Jum. II - 10 Jum. II
Quality Inn
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See all available properties in Winchester
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.

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 9 places to stay with pools. While you’re here, you can explore sights such as Shenandoah Valley Discovery Museum and Museum of the Shenandoah Valley, and then unwind poolside at one of the accommodations in Winchester that guests like for their pools.
How many hotels with pools will I find in Winchester?
Expedia has 9 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 Nalls Farm Market. During your stay, check out sights such as Museum of the Shenandoah Valley, Jim Barnett Park, and Apple Blossom Mall. 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.

Recent reviews of Winchester hotels
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

5/5 Excellent
"Dog friendly and very convenient to I-81 on/off ramp."
A verified traveler stayed at La Quinta Inn & Suites by Wyndham Winchester
Posted 14 hours ago
La Quinta Inn & Suites by Wyndham Winchester