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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Winchester

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
Winchester Home w/ Views Near Tims Ford Lake!
Exterior

Winchester Home w/ Views Near Tims Ford Lake!

3.0 star property
Winchester Home w/ Views Near Tims Ford Lake!
Cozy Cottage w/ Private Yard: Pet Friendly!
Interior

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!
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!
Modern Tims Ford Lake Home w/ Private Dock & Pool!
Interior

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!
Interior

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!
Cozy Shelbyville Home Near Hiking & Distilleries!
Exterior

Cozy Shelbyville Home Near Hiking & Distilleries!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This home was cozy, Insode was superb, ouside grass could have been cut, but overall it was nice."
Cozy Shelbyville Home Near Hiking & Distilleries!
Tullahoma Vacation Rental < 8 Mi to Lynchburg!
Interior

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!
Charming Tullahoma Stay w/ Great Walkable Location
Interior

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
'valley View Lodge' Rural Home in Bridgeport!
Interior

'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!
Waterfront Oasis On Tims Ford Lake: Pool/kayak!
Interior

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!
Modern Luxury Retreat: Walk to Tims Ford Lake!
Exterior

Modern Luxury Retreat: Walk to Tims Ford Lake!

3.0 star property
Modern Luxury Retreat: Walk to Tims Ford Lake!
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!
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!
Winchester Home w/ Deck < 1 Mi to Tims Ford Lake!
Interior

Winchester Home w/ Deck < 1 Mi to Tims Ford Lake!

3.0 star property
Winchester Home w/ Deck < 1 Mi to Tims Ford Lake!
'paradise Found' Lake House on Waterfront!
Front of property

'paradise Found' Lake House on Waterfront!

3.0 star property
'paradise Found' Lake House on Waterfront!
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

Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

10/10 Excellent
"Musty smell in the room, but clean and comfortable. Basic breakfast. For the price, it was great. "
Katherine 1-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Manchester

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.