A calm lake with autumn foliage, a dock, and houses along the shore.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Winchester vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Oasis on the Square

Oasis on the Square
Winchester
9.8 out of 10, Exceptional, (13 reviews)
"Great location on the square with plenty of dining options a short walk away."
United States
possible Amanda H
The price is ￥12,037
￥26,530 total
includes taxes & fees
Aug 13 - Aug 14
Oasis on the Square
Interior

2. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.4 out of 10, Exceptional, (15 reviews)
"It was wonderful and right in the center of downtown winchester. Very clean and beautiful loft and amazing lighting to have long night talks. Truly amazing"
United States
Gianmarco
The price is ￥14,514
￥29,708 total
includes taxes & fees
Aug 12 - Aug 13
Winchester's Premier Downtown Loft!
Interior

3. Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Winchester
10.0 out of 10, Exceptional, (7 reviews)
"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "
United States
Gwen K.
The price is ￥47,297
￥113,362 total
includes taxes & fees
Aug 12 - Aug 13
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Terrace/patio

4. The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Right on the water and next to the marina, great location! We stayed over Christmas week. We will be returning in the summer so we can enjoy the lake!"
United States
Andy D.
The price is ￥93,018
￥162,279 total
includes taxes & fees
Sep 10 - Sep 11
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Outdoor dining

5. Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Winchester
10.0 out of 10, Exceptional, (81 reviews)
"We had a great time! "
United States
Cindy O.
The price is ￥85,190
￥151,449 total
includes taxes & fees
Aug 16 - Aug 17
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Smart TV, table tennis

6. Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Winchester
10.0 out of 10, Exceptional, (25 reviews)
"What a lovely property and the perfect stay for a large family! We had a great time and the host is very gracious and accommodating. The home was well stocked and had all of the amenities we could have wanted. We had no issues, but the host was very communicative and I'm confident any issue would have been resolved promptly. I highly recommend this home, as well as any other listings from this host!"
United States
Lisa A.
The price is ￥58,213
￥111,378 total
includes taxes & fees
Sep 9 - Sep 10
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Outdoor dining

7. "The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.2 out of 10, Wonderful, (24 reviews)
"Great little, hidden get-away!"
United States
Rich F.
The price is ￥43,384
￥72,727 total
includes taxes & fees
Aug 20 - Aug 21
"The Hawk Nest" cabin on Tims Ford Lake
Microwave, oven, stovetop, dishwasher

8. Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups
Winchester
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay! "
United States
Erica P.
The price is ￥14,333
￥27,232 total
includes taxes & fees
Aug 17 - Aug 18
Tiny Home w/ RV Hookups
Outdoor dining

9. Stationary tiny camper in Winchester, TN with pond and mountain views.

Stationary tiny camper in Winchester, TN with pond and mountain views.
Winchester
10.0 out of 10, Exceptional, (1 review)
"I definitely give this property 5 gold stars in all categories. It was EXACTLY as advertised with the owner taking care to provide little 'extras' on top of that in the form of snacks, coffee, etc... The electric awning is not even mentioned, but it makes a nice outside sitting area with the provided picnic table. The tiny camper is perfect for a night or a few for 1-2 people. Very clean, great communication and all the things you would want."
United States
Jr H.
The price is ￥12,779
￥23,390 total
includes taxes & fees
Sep 9 - Sep 10
Stationary tiny camper in Winchester, TN with pond and mountain views.
Smart TV, fireplace, stereo

10. Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC

Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
Winchester
7.0 out of 10, Good, (6 reviews)
"This property was perfect for our family and is very close to the marina. Would definitely stay again! "
United States
Emily C.
The price is ￥15,476
￥24,942 total
includes taxes & fees
Sep 9 - Sep 10
Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
House, 5 Bedrooms | Marina

11. Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
3.0 star property
Winchester
The price is ￥93,675
￥200,387 total
includes taxes & fees
Sep 7 - Sep 8
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Property grounds

12. Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Winchester
10.0 out of 10, Exceptional, (37 reviews)
"Very nice! "
United States
Adam H.
The price is ￥47,170
￥96,233 total
includes taxes & fees
Sep 9 - Sep 10
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Coffee/tea maker, fridge, microwave, oven

13. Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!

Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Pelham
9.6 out of 10, Exceptional, (35 reviews)
"House is kept in great condition, beautiful location, and perfect stay when attending the caverns (12 minutes away)"
United States
Antonio M.
The price is ￥11,043
￥41,683 total
includes taxes & fees
Sep 9 - Sep 10
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Outdoor dining

14. A very rustic converted pole barn unique cozy cabin

A very rustic converted pole barn unique cozy cabin
Estill Springs
9.8 out of 10, Exceptional, (162 reviews)
"Our stay was comfortable and clean."
United States
George A.
The price is ￥15,776
￥22,875 total
includes taxes & fees
Aug 26 - Aug 27
A very rustic converted pole barn unique cozy cabin
Interior

15. Queen ensuite room in historic railroad inn & town. Continental breakfast.

Queen ensuite room in historic railroad inn & town. Continental breakfast.
Cowan
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful spot!"
United States
Bennett R.
The price is ￥19,720
￥22,875 total
includes taxes & fees
Sep 9 - Sep 10
Queen ensuite room in historic railroad inn & town. Continental breakfast.
Outdoor dining

16. Story-time Stay at Our Rupert Cottage!

Story-time Stay at Our Rupert Cottage!
Monteagle
8.8 out of 10, Excellent, (6 reviews)
"Pet friendly, host communication was excellent. The cottage was tidy and clean. "
United States
Taroub F.
The price is ￥10,128
￥33,743 total
includes taxes & fees
Sep 9 - Sep 10
Story-time Stay at Our Rupert Cottage!
Interior

17. Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
10.0 out of 10, Exceptional, (4 reviews)
"Awesome place"
United States
Casey C.
The price is ￥6,310
￥18,205 total
includes taxes & fees
Aug 19 - Aug 20
Boutique Suite in Historic Tracy City!
TV, fireplace

18. Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.2 out of 10, Wonderful, (13 reviews)
"Super clean, great location and spacious! "
United States
Karen W.
The price is ￥10,728
￥30,890 total
includes taxes & fees
Sep 9 - Sep 10
Hiker's Hangout Monteagle
Terrace/patio

19. Newly Remodled Suite in Monteagle TN!

Newly Remodled Suite in Monteagle TN!
Monteagle
9.4 out of 10, Exceptional, (12 reviews)
"comfy and cute stay!"
United States
Kylee
The price is ￥8,440
￥27,783 total
includes taxes & fees
Sep 3 - Sep 4
Newly Remodled Suite in Monteagle TN!
Lobby

20. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is ￥12,424
￥32,848 total
includes taxes & fees
Aug 12 - Aug 13
Whiskey Trails Cottage
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
"Great place for the value"
Lisa 1-night trip
Posted 9 hours ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we have vacation rentals in Winchester close to Twin Creeks Marina, or you can select a secluded option if you're looking for extra privacy while you relax. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffeehouses during your trip.

What are some of the best vacation home rentals in Winchester?

Private dock/gazebo on quiet cove. Tims Ford Lake!: Visitors like this Winchester vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Winchester are Lakefront w/Private Dock and Walk to Historic Downtown Winchester! and Spacious Family Gem: Golf Cart - 2 Ensuites - Pool.

How many vacation rentals are there in Winchester?

Expedia has 115 vacation rentals for your stay in Winchester.

What can I see and do in Winchester?

Family-friendly attractions include Twin Creeks Marina and Tim's Ford Marina, whereas Tims Ford Lake and Elk River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tims Ford State Park and Franklin County Farmers Market.

What are vacation rentals like in Winchester?

Vacation rentals are private accommodations you can reserve for a short or long stay in Winchester. Vacation rentals feature extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family gatherings.