Holiday Homes in Winchester

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Featured Holiday Homes in Winchester

Shea's Chalet - Cozy home in Monteagle, TN
Exterior

Shea's Chalet - Cozy home in Monteagle, TN

2.0 star property
9.8 out of 10, Exceptional, (12)
"Good location "
The price is AU$426
includes taxes & fees
28 Sept - 29 Sept
Shea's Chalet - Cozy home in Monteagle, TN
Mountain Point of View Cottage
Exterior

Mountain Point of View Cottage

9.6 out of 10, Exceptional, (23)
"Loved the location of this place. Everything was neat and clean. If you are looking for a relaxing, peaceful stay in Pelham, this is the place to go!"
The price is AU$293
includes taxes & fees
29 Sept - 30 Sept
Mountain Point of View Cottage
Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!
Fridge, microwave, oven, stovetop

Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!

9.6 out of 10, Exceptional, (133)
"House was conveniently located and very clean. Provided the "
Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
Exterior

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

10.0 out of 10, Exceptional, (19)
"The stay was amazing. The house was exactly as described. 100% recommend couldn’t have been happier and we will be back. "
The price is AU$489
includes taxes & fees
7 Oct - 8 Oct
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
Whispering Woods Tracy City
Exterior

Whispering Woods Tracy City

2.0 star property
9.4 out of 10, Exceptional, (9)
"Comfortable, quiet, everything you need, stores close. Short drive to two great OHV parks. "
The price is AU$359
includes taxes & fees
28 Sept - 29 Sept
Whispering Woods Tracy City
Forest Retreat: Poolside Bliss Close to Campus
3 bedrooms, free WiFi, bed sheets

Forest Retreat: Poolside Bliss Close to Campus

The price is AU$642
includes taxes & fees
28 Sept - 29 Sept
Forest Retreat: Poolside Bliss Close to Campus
3-Br Luxury Home with Hot Tub & Arcade Games
Outdoor spa tub

3-Br Luxury Home with Hot Tub & Arcade Games

10.0 out of 10, Exceptional, (26)
"Want your own cozy cabin, this is it. Absolutely perfect!"
3-Br Luxury Home with Hot Tub & Arcade Games
Remodeled Cottage with Sunroom
Fridge, microwave, oven, stovetop

Remodeled Cottage with Sunroom

9.4 out of 10, Exceptional, (14)
"Grandson loved the goats at the neighbors. Plenty of room fou us all."
The price is AU$429
includes taxes & fees
29 Sept - 30 Sept
Remodeled Cottage with Sunroom
Reflection Bay-Dock, Hot Tub, Kayaks
Fridge, microwave, oven, stovetop

Reflection Bay-Dock, Hot Tub, Kayaks

10.0 out of 10, Exceptional, (11)
"Great communication and great location "
Reflection Bay-Dock, Hot Tub, Kayaks
High Point Getaway - Monteagle
Exterior

High Point Getaway - Monteagle

2.0 star property
9.4 out of 10, Exceptional, (8)
"Great property worked well for large group"
The price is AU$520
includes taxes & fees
30 Sept - 1 Oct
High Point Getaway - Monteagle
Mid-Century Estate - Home/Loft - Hot Tub/Game Room
Terrace/patio

Mid-Century Estate - Home/Loft - Hot Tub/Game Room

10.0 out of 10, Exceptional, (7)
"My group really enjoyed our stay. It was perfect for our trip."
The price is AU$1,160
includes taxes & fees
19 Oct - 20 Oct
Mid-Century Estate - Home/Loft - Hot Tub/Game Room
Time Well Wasted on the Lake
Exterior

Time Well Wasted on the Lake

The price is AU$300
includes taxes & fees
28 Sept - 29 Sept
Time Well Wasted on the Lake
Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village
Fridge, microwave, oven, stovetop

Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village

10.0 out of 10, Exceptional, (3)
"Great location, easy in and out. Thanks John!"
Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village
Sewanee Woods Modern Luxe Escape
Smart TV, fireplace, ping pong, books

Sewanee Woods Modern Luxe Escape

9.8 out of 10, Exceptional, (8)
"Lovely home with responsive and helpful host. Perfect location for visiting our kids at Sewanee. We will definitely return! "
The price is AU$879
includes taxes & fees
29 Sept - 30 Sept
Sewanee Woods Modern Luxe Escape
Gorgeous Renovated Home with Open Floor Plan and Large Lot
Interior

Gorgeous Renovated Home with Open Floor Plan and Large Lot

9.0 out of 10, Wonderful, (16)
"We enjoyed the cottages roomie interior and comfortable beds. We saw a deer enjoyed walking the dog around the property and had a peaceful night sleep."
The price is AU$482
includes taxes & fees
29 Sept - 30 Sept
Gorgeous Renovated Home with Open Floor Plan and Large Lot
On the University of the South campus, Sewanee, TN.
Terrace/patio

On the University of the South campus, Sewanee, TN.

9.8 out of 10, Exceptional, (21)
"The home is a perfect cozy retreat and great location on campus! "
The price is AU$812
includes taxes & fees
7 Oct - 8 Oct
On the University of the South campus, Sewanee, TN.
Larger Home in Tracy City, TN Tiny Home Lake & Community-Retreat at Water's Edge
Property grounds

Larger Home in Tracy City, TN Tiny Home Lake & Community-Retreat at Water's Edge

10.0 out of 10, Exceptional, (19)
"We had a great time at your little home "
The price is AU$599
includes taxes & fees
30 Sept - 1 Oct
Larger Home in Tracy City, TN Tiny Home Lake & Community-Retreat at Water's Edge
NEW! Tim's Ford Lakefront Home
Terrace/patio

NEW! Tim's Ford Lakefront Home

10.0 out of 10, Exceptional, (19)
"Beautiful home. Had everything we needed and more. Will be back for sure "
NEW! Tim's Ford Lakefront Home
Tennessee Getaway (near Jack Daniel’s and Nearest Green distilleries)
Terrace/patio

Tennessee Getaway (near Jack Daniel’s and Nearest Green distilleries)

10.0 out of 10, Exceptional, (52)
"Beautiful home , enjoyed sitting outside for coffee in the morning.Really enjoyed our stay!"
The price is AU$491
includes taxes & fees
30 Sept - 1 Oct
Tennessee Getaway (near Jack Daniel’s and Nearest Green distilleries)
Lulu's Place - A Lakeside Tiny Home in Tennessee
Smart TV, fireplace

Lulu's Place - A Lakeside Tiny Home in Tennessee

10.0 out of 10, Exceptional, (11)
"Lovely and very clean tiny home with a beautiful porch in a quiet location."
The price is AU$481
includes taxes & fees
5 Oct - 6 Oct
Lulu's Place - A Lakeside Tiny Home in Tennessee
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"The room was clean the towels were fluffy and the sheets were crisp. Despite the highway being very close it couldn’t be heard. The staff was very nice and had great recommendations for supper. Would stay there again."
Jill 1-night trip
Posted 2 days ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
381
Accommodation
318 Holiday Homes
Lowest Price
AU$293
Highest Price
AU$1,160

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