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Compare 355 Vacation Homes in Winchester with updated reviews, rates, and availability.

Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!
Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!
9.6 out of 10, Exceptional, (118)

Mountain Memories to provide a cozy retreat on your vacation!
Mountain Memories to provide a cozy retreat on your vacation!
9.8 out of 10, Exceptional, (17)
The price is SAR 338
SAR 785 total
includes taxes & fees
31 Mar - 1 Apr

Mountain Point of View Cottage
Mountain Point of View Cottage
9.8 out of 10, Exceptional, (17)
The price is SAR 244
SAR 664 total
includes taxes & fees
1 Apr - 2 Apr

Camp McGu: Lakefront, Boats Included, 3 Fireplaces + Firepit, Gorgeous Setting
Camp McGu: Lakefront, Boats Included, 3 Fireplaces + Firepit, Gorgeous Setting
10.0 out of 10, Exceptional, (10)

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
10.0 out of 10, Exceptional, (2)
The price is SAR 581
SAR 1,209 total
includes taxes & fees
3 Apr - 4 Apr

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart
Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart
9.8 out of 10, Exceptional, (20)

Eagle's Point - Sleeps 12 with an incredible view!
Eagle's Point - Sleeps 12 with an incredible view!
9.8 out of 10, Exceptional, (102)

Shea's Chalet - Cozy home in Monteagle, TN
Shea's Chalet - Cozy home in Monteagle, TN
9.6 out of 10, Exceptional, (5)
The price is SAR 345
SAR 1,165 total
includes taxes & fees
1 Apr - 2 Apr
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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Other property types in Winchester

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10.0 out of 10, Exceptional, (23)

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart
Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart
9.8 out of 10, Exceptional, (20)

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
10.0 out of 10, Exceptional, (41)
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.
Recent reviews of Winchester hotels
Recent reviews of Winchester hotels

Best Western Inn
5/5 Excellent
"Stayed several times in December 2024. Always kind and they had a great breakfast"
A verified traveler stayed at Best Western Inn
Posted 2 days ago
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