Search Hotels with Pool in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winchester Hotels with Pool

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Winchester hotels with a pool

Outdoor pool, pool loungers
Best Western Inn

Best Western Inn

Best Western Inn
2.5 star property
Winchester
8.8 out of 10, Excellent, (664)
"front desk guy was great, went above and beyond"
United States
Nicholas
The price is ฿2,910
฿3,325 total
includes taxes & fees
28 Dec - 29 Dec
Best Western Inn
Terrace/patio
The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins
3.0 star property
Monteagle
8.6 out of 10, Excellent, (1142)
"We always stop here in our way to Kentucky. Nice and quiet and staff is nice"
United States
Kevin
The price is ฿1,539
฿1,766 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Smokehouse Lodge and Cabins
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool umbrellas
Quality Inn Monteagle

Quality Inn Monteagle

Quality Inn Monteagle
2.5 star property
Downtown Monteagle
8.8 out of 10, Excellent, (819)
"nice comfy beds and a solid breakfast in the morning "
United States
Justin
The price is ฿2,450
฿2,922 total
includes taxes & fees
8 Jan - 9 Jan 2026
Quality Inn Monteagle
Indoor pool
Comfort Suites Manchester near Arnold AFB

Comfort Suites Manchester near Arnold AFB

Comfort Suites Manchester near Arnold AFB
2.5 star property
Manchester
9.4 out of 10, Exceptional, (935)
"Spotless room, great layout, good breakfast food, reasonably priced stay. "
United States
Carl
The price is ฿2,940
฿3,476 total
includes taxes & fees
28 Dec - 29 Dec
Comfort Suites Manchester near Arnold AFB
Outdoor pool, pool loungers
Spark by Hilton Kimball

Spark by Hilton Kimball

Spark by Hilton Kimball
2.5 star property
Jasper
8.4 out of 10, Very good, (1001)
"The room was clean and comfortable "
United States
Miguel Eduardo
The price is ฿2,395
฿2,748 total
includes taxes & fees
10 Jan - 11 Jan 2026
Spark by Hilton Kimball
Lobby
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester
2.0 star property
Manchester
8.6 out of 10, Excellent, (1003)
"Staff was kind and informative. "
United States
Mitra
The price is ฿1,976
฿2,336 total
includes taxes & fees
24 Dec - 25 Dec
Microtel Inn & Suites by Wyndham Manchester
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.
View all properties

Top Winchester Hotel Reviews

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"The room was spotless. It was the perfect atmosphere before a day on the trails at Coalmont. ONLY suggestion Id have is put a fluffy comforter on the bed. Thank you! Ps. We loved it."
Tambra 1-night trip
Posted 12 days ago
The Smokehouse Lodge and Cabins

Frequently asked questions

What are some accommodation options with pools in Winchester?
Best Western Inn: Features full, a seasonal outdoor pool and complimentary high-speed (wired) Internet access. The Smokehouse Lodge and Cabins: Offers kitchens, a pool and flat-screen televisions. Microtel Inn & Suites by Wyndham Manchester: Provides sunloungers, a communal pool and complimentary wireless Internet access. Spark by Hilton Kimball: Features free self parking, an outdoor pool and flat-screen televisions. The Sewanee Inn: Offers daily, an outdoor pool and free self parking.
What is there to see and do in Winchester?
The picturesque setting of Tims Ford and Tims Ford Lake showcase the area's natural beauty. During your stay, visit sights such as Twin Creeks Marina, Tim's Ford Marina and Tims Ford State Park.
When is the best time to book a hotel with a pool in Winchester?
You may want to consider accommodation with an outdoor swimming pool if you'll be visiting Winchester in the hottest months of July, August or June, when the average temperature is 24°C. Accommodation with 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 6°C.