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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Winchester vacation rentals

Interior

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.4 out of 10, Exceptional, (16 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 SAR 389
SAR 764 total
includes taxes & fees
21 Sep - 22 Sep
Winchester's Premier Downtown Loft!
Coffee/tea maker, fridge, microwave, oven

2. 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 SAR 368
SAR 730 total
includes taxes & fees
21 Sep - 22 Sep
Oasis on the Square
Microwave, oven, stovetop, dishwasher

3. 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 SAR 335
SAR 682 total
includes taxes & fees
25 Aug - 26 Aug
Tiny Home w/ RV Hookups
Outdoor dining

4. "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 SAR 559
SAR 1,256 total
includes taxes & fees
24 Aug - 25 Aug
"The Hawk Nest" cabin on Tims Ford Lake
Interior

5. 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 SAR 1,115
SAR 2,830 total
includes taxes & fees
5 Sep - 6 Sep
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Smart TV, fireplace, stereo

6. 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 SAR 368
SAR 630 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
Outdoor dining

7. 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 SAR 304
SAR 600 total
includes taxes & fees
30 Aug - 31 Aug
Stationary tiny camper in Winchester, TN with pond and mountain views.
Terrace/patio

8. 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 Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Smart TV, table tennis

9. 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 SAR 1,314
SAR 2,729 total
includes taxes & fees
13 Sep - 14 Sep
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Terrace/patio

10. Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (20 reviews)
"This is a fabulous lake house! The view and amenities are perfect! "
United States
Andrea M.
Lakefront Lodge on Tims Ford Lake
Outdoor dining

11. 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, (82 reviews)
"We had a great time! "
United States
Cindy O.
The price is SAR 2,253
SAR 4,036 total
includes taxes & fees
20 Sep - 21 Sep
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
House, 5 Bedrooms | Marina

12. 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 SAR 2,172
SAR 4,703 total
includes taxes & fees
31 Aug - 1 Sep
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Property grounds

13. 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 SAR 1,498
SAR 2,859 total
includes taxes & fees
24 Aug - 25 Aug
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Coffee/tea maker, fridge, microwave, oven

14. 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, (36 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 SAR 263
SAR 992 total
includes taxes & fees
1 Sep - 2 Sep
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Outdoor dining

15. 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, (163 reviews)
"This was a perfect stay for us while we were visiting family! We look forward to staying again when we’re in the area."
United States
Jacquelyne S.
The price is SAR 375
SAR 577 total
includes taxes & fees
24 Aug - 25 Aug
A very rustic converted pole barn unique cozy cabin
Lobby

16. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is SAR 296
SAR 782 total
includes taxes & fees
25 Aug - 26 Aug
Whiskey Trails Cottage
Interior

17. Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns

Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Pelham
10.0 out of 10, Exceptional, (6 reviews)
"This place was absolutely beautiful. Perfect size for my husband and I and close proximity to The Caverns. We had a wonderful stay! We will definitely be returning!"
United States
Kimberley D.
The price is SAR 244
SAR 726 total
includes taxes & fees
24 Aug - 25 Aug
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
WiFi (free), bed sheets

18. Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
9.4 out of 10, Exceptional, (8 reviews)
"Omgoodness this place is absolutely amazing!!! We went for a spiritual journey and it was perfect!! The lake & water fall creek with seats sitting in the water was perfect for my reading and meditating. It is absolutely beautiful!!! They had a concert Saturday night, we didn't go to the actual concert but was right beside it and they were fabulous!! Great place to stay! We will definitely return. Thank you so much for everything!"
United States
Tina
The price is SAR 321
SAR 368 total
includes taxes & fees
26 Aug - 27 Aug
Sasquatch Farm
House (3 Bedrooms) | Interior

19. Lakes, Whiskey & More! Charming Home in Tullahoma

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is SAR 473
SAR 1,363 total
includes taxes & fees
7 Sep - 8 Sep
Lakes, Whiskey & More! Charming Home in Tullahoma
Smart TV, fireplace, DVD player

20. Deciduous Dreams in Deer Lick Falls

Deciduous Dreams in Deer Lick Falls
Monteagle
9.0 out of 10, Wonderful, (14 reviews)
"Loved our stay here - such a cozy little tiny home community, private but not isolated. We loved the hike to the waterfall on the property grounds, as well as the gorgeous Fiery Gizzard North trailhead with several other waterfalls just a short drive away. "
United States
Claire H.
The price is SAR 282
SAR 773 total
includes taxes & fees
1 Sep - 2 Sep
Deciduous Dreams in Deer Lick Falls
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
"This is our third time stopping over at this great place. The staff is incredibly nice and most importantly it’s clean."
Lillie 1-night trip
Posted 1 day ago
The Smokehouse Lodge and Cabins

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 New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks.

How many vacation rentals are there in Winchester?

Expedia has 114 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 Hammers.

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.