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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Featured Cottages in Winchester

On-site Trails + Furnished Deck: Monteagle Escape!
Interior

On-site Trails + Furnished Deck: Monteagle Escape!

3.0 star property
On-site Trails + Furnished Deck: Monteagle Escape!
Tracy City Home Near South Cumberland State Park!
Exterior

Tracy City Home Near South Cumberland State Park!

3.0 star property
Tracy City Home Near South Cumberland State Park!
Winchester Home w/ Views Near Tims Ford Lake!
Interior

Winchester Home w/ Views Near Tims Ford Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The property was clean and well maintained in an area that was relatively quiet. "
Winchester Home w/ Views Near Tims Ford Lake!
Modern Luxury Retreat: Walk to Tims Ford Lake!
Interior

Modern Luxury Retreat: Walk to Tims Ford Lake!

3.0 star property
Modern Luxury Retreat: Walk to Tims Ford Lake!
Modern Tims Ford Lake Home w/ Private Dock & Pool!
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Modern Tims Ford Lake Home w/ Private Dock & Pool!

3.0 star property
Modern Tims Ford Lake Home w/ Private Dock & Pool!
Cozy Tennessee Cabin w/ Deck, Grill & Fire Pit!
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Cozy Tennessee Cabin w/ Deck, Grill & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Well kept small cabin near the Holiday Marina at Tims Ford Lake. Not on the water but close to the boat launch and marina with a restaurant and bar. Everything works and the property was clean and well stocked. The house is small but there are plenty of beds with three bedrooms, two loft areas and three full baths. "
Cozy Tennessee Cabin w/ Deck, Grill & Fire Pit!
'valley View Lodge' Rural Home in Bridgeport!
Front of property

'valley View Lodge' Rural Home in Bridgeport!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place"
'valley View Lodge' Rural Home in Bridgeport!
Cozy Tennessee Abode w/ Private Hot Tub & Fire Pit
Front of property

Cozy Tennessee Abode w/ Private Hot Tub & Fire Pit

3.0 star property
Cozy Tennessee Abode w/ Private Hot Tub & Fire Pit
Tullahoma Vacation Rental < 8 Mi to Lynchburg!
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Tullahoma Vacation Rental < 8 Mi to Lynchburg!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The size of the property easily accommodated the 8 of us. Beds are comfy, plenty of seating room in the living areas. Plenty of parking as well as a nice outdoor seating arrangement "
Tullahoma Vacation Rental < 8 Mi to Lynchburg!
Cozy Cottage w/ Private Yard: Pet Friendly!
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Cozy Cottage w/ Private Yard: Pet Friendly!

3.0 star property
9.0 out of 10, Wonderful, (2)
"We had a wonderful stay. Everything was renovated and clean. We will definitely come back!"
Cozy Cottage w/ Private Yard: Pet Friendly!
Charming Tullahoma Stay w/ Great Walkable Location
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Charming Tullahoma Stay w/ Great Walkable Location

3.0 star property
Charming Tullahoma Stay w/ Great Walkable Location
Normandy Home w/ Yard ~ 2 Mi to Lake
Interior

Normandy Home w/ Yard ~ 2 Mi to Lake

3.0 star property
9.0 out of 10, Wonderful, (2)
"Everything was perfect for our group! And the owner was very communicative. "
Normandy Home w/ Yard ~ 2 Mi to Lake
Waterfront Oasis On Tims Ford Lake: Pool/kayak!
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Waterfront Oasis On Tims Ford Lake: Pool/kayak!

3.0 star property
Waterfront Oasis On Tims Ford Lake: Pool/kayak!
Serene Cabin w/ Riverfront Views & Access!
Interior

Serene Cabin w/ Riverfront Views & Access!

3.0 star property
Serene Cabin w/ Riverfront Views & Access!
Twin Creeks Resort Cottages
Terrace/patio

Twin Creeks Resort Cottages

3.0 star property
Twin Creeks Resort Cottages
Spacious Lakefront Retreat w/ Hot Tub + Dock!
Interior

Spacious Lakefront Retreat w/ Hot Tub + Dock!

3.0 star property
Spacious Lakefront Retreat w/ Hot Tub + Dock!
Historic Hawkins House Located on Sewanee Campus
Front of property

Historic Hawkins House Located on Sewanee Campus

3.0 star property
Historic Hawkins House Located on Sewanee Campus
Winchester Home w/ Deck < 1 Mi to Tims Ford Lake!
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Winchester Home w/ Deck < 1 Mi to Tims Ford Lake!

3.0 star property
Winchester Home w/ Deck < 1 Mi to Tims Ford Lake!
Lak Haus: Resort-style Home on Tims Ford Lake!
Interior

Lak Haus: Resort-style Home on Tims Ford Lake!

3.0 star property
Lak Haus: Resort-style Home on Tims Ford Lake!
Group Getaway: Lakefront Retreat in Fayetteville!
Interior

Group Getaway: Lakefront Retreat in Fayetteville!

3.0 star property
Group Getaway: Lakefront Retreat in Fayetteville!
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

Quality Inn Monteagle

Quality Inn Monteagle

10/10 Excellent
"Was very clean, staff were super friendly, highly recommend "
Payton 1-night trip
Posted 6 days ago
Quality Inn Monteagle

Find out more about Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
7
Accommodation
26 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Winchester with Expedia?
Expedia has some excellent cottages in Winchester, so start packing for an unforgettable stay on nature's doorstep. If you have a fixed budget, select how much you're willing to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We'll help you find the right place whatever your bank balance or plans.
How can I find cheap cottages in Winchester?
An excellent way to find cheap cottages in Winchester is with Expedia's user-friendly filter tool. Narrow your search by budget, star rating and amenities to take advantage of unbeatable rates in just a few keystrokes.
What is there to do in Winchester near my cottage?
The most useful travel accessory is a well-planned itinerary. Tim's Ford Marina is a terrific place to start your exploration of Winchester.

Explore a world of travel with Expedia

Explore a world of travel with Expedia