Hotels with Pool & Resorts in Winchester from AU$80

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
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Best Winchester Hotels with Pool

Outdoor pool, pool loungers
Best Western Inn

Best Western Inn

2.5 star property
Winchester
8.8 out of 10, Excellent, (658)
"Staff was very efficient at check in. The room was nice and clean. Would stay there again. "
United States
Amanda
The price is AU$174
includes taxes & fees
10 Dec - 11 Dec
Best Western Inn
Smart TV, fireplace
The Lakefront Getaway

The Lakefront Getaway

2.0 star property
Winchester
9.6 out of 10, Exceptional, (5)
"Incredible "
United States
Jim C.
The price is AU$691
includes taxes & fees
14 Dec - 15 Dec
The Lakefront Getaway
Smart TV, fireplace
Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Winchester
10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay. The home was great! Everything you need. Love the location. Close to Winchester and the lake. Highly recommend. Already planning to stay there again."
United States
Gary W.
The price is AU$754
includes taxes & fees
25 Dec - 26 Dec
Luxurious Lakefront Home- Marina, Boats, and Kayaks!
Outdoor pool
Lakeview Luxe - Lake Access + Pool

Lakeview Luxe - Lake Access + Pool

2.0 star property
Winchester
10.0 out of 10, Exceptional, (3)
"Had a great stay and would recommend this property to all!"
United States
Lizzie S.
The price is AU$940
includes taxes & fees
9 Dec - 10 Dec
Lakeview Luxe - Lake Access + Pool
Pool
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

2.0 star property
Winchester
10.0 out of 10, Exceptional, (1)
"Very clean, many extras in the house. Nice location, close to Winchester and the marina. We all enjoyed it from 11 years old, teenagers to adults."
United States
Greg S.
The price is AU$646
includes taxes & fees
22 Dec - 23 Dec
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.
Pool
Lakeside Tims Ford Lakehouse Resort Style Pool, Lake Balcony, Firepits, Hot Tub.

Lakeside Tims Ford Lakehouse Resort Style Pool, Lake Balcony, Firepits, Hot Tub.

Winchester
The price is AU$814
includes taxes & fees
2 Jan - 3 Jan 2026
Lakeside Tims Ford Lakehouse Resort Style Pool, Lake Balcony, Firepits, Hot Tub.
Outdoor pool, pool umbrellas, pool loungers
The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3.0 star property
Monteagle
8.6 out of 10, Excellent, (1145)
"We always stop here in our way to Kentucky. Nice and quiet and staff is nice"
United States
Kevin
The price is AU$80
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

2.5 star property
Downtown Monteagle
8.8 out of 10, Excellent, (814)
"nice comfy beds and a solid breakfast in the morning "
United States
Justin
The price is AU$140
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

2.5 star property
Manchester
9.4 out of 10, Exceptional, (924)
"Spotless room, great layout, good breakfast food, reasonably priced stay. "
United States
Carl
The price is AU$170
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Suites Manchester near Arnold AFB
Lobby
Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

2.0 star property
Manchester
8.6 out of 10, Excellent, (992)
"Great place very clean"
United States
Bradley
The price is AU$112
includes taxes & fees
10 Dec - 11 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

Clarion Pointe Kimball By Choice Hotels

Clarion Pointe Kimball By Choice Hotels

10/10 Excellent
"A few long black hairs on towel and comforter "
Jeff 1-night trip
Posted 4 days ago
Clarion Pointe Kimball By Choice Hotels

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. Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak: Offers kitchens, a pool and flat-screen televisions. Beautiful Lake Views at Twin Creeks!: Features sunloungers, a communal pool and complimentary wireless Internet access. Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs: Offers free self parking, an outdoor pool and flat-screen televisions. Gorgeous Renovated Home with Open Floor Plan and Large Lot: Provides 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.