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

Winchester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winchester holiday 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 HK$811
HK$1,596 total
includes taxes & fees
7 Sept - 8 Sept
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 HK$769
HK$1,540 total
includes taxes & fees
31 Aug - 1 Sept
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 HK$776
HK$1,606 total
includes taxes & fees
31 Aug - 1 Sept
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 HK$1,168
HK$2,815 total
includes taxes & fees
31 Aug - 1 Sept
"The Hawk Nest" cabin on Tims Ford Lake
Marina

5. 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 HK$4,824
HK$10,152 total
includes taxes & fees
31 Aug - 1 Sept
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Outdoor dining

6. 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 HK$635
HK$1,253 total
includes taxes & fees
5 Sept - 6 Sept
Stationary tiny camper in Winchester, TN with pond and mountain views.
Interior

7. 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 HK$2,329
HK$6,342 total
includes taxes & fees
1 Sept - 2 Sept
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Smart TV, ping pong

8. 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)
The price is HK$2,744
HK$6,134 total
includes taxes & fees
13 Sept - 14 Sept
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Terrace/patio

9. 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 HK$5,042
HK$8,817 total
includes taxes & fees
10 Sept - 11 Sept
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Outdoor dining

10. 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 HK$4,234
HK$8,597 total
includes taxes & fees
31 Aug - 1 Sept
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

11. 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.
The price is HK$5,488
HK$9,167 total
includes taxes & fees
9 Sept - 10 Sept
Lakefront Lodge on Tims Ford Lake
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, (38 reviews)
"Very nice! "
United States
Adam H.
The price is HK$3,128
HK$6,492 total
includes taxes & fees
31 Aug - 1 Sept
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Outdoor dining

13. 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, (164 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 HK$784
HK$1,296 total
includes taxes & fees
31 Aug - 1 Sept
A very rustic converted pole barn unique cozy cabin
Interior

14. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is HK$617
HK$1,632 total
includes taxes & fees
31 Aug - 1 Sept
Whiskey Trails Cottage
Interior

15. 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, (10 reviews)
"Nice place to stay. Close to the caverns where we saw a show. Property is very clean. Really nice stay."
United States
Dawn
The price is HK$517
HK$1,525 total
includes taxes & fees
31 Aug - 1 Sept
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Free WiFi, bed sheets

16. 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 HK$670
HK$769 total
includes taxes & fees
31 Aug - 1 Sept
Sasquatch Farm
Interior

17. Cove Sweet Cove - 3BR + 2BR Near the Caverns!

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
9.8 out of 10, Exceptional, (8 reviews)
"The cabin was just as advertised. It was clean and perfect location for the concert at the cavern. I would book again."
United States
Joanne G.
The price is HK$557
HK$1,984 total
includes taxes & fees
31 Aug - 1 Sept
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
1 bedroom, Internet, bed sheets

18. Snuggle Up in our Teddy Cottage! *New Listing*

Snuggle Up in our Teddy Cottage! *New Listing*
Monteagle
10.0 out of 10, Exceptional, (7 reviews)
"I really enjoyed my stay here with my girlfriend and our two dogs. The cottage & surrounding area is super cute and cozy. There is also a nice walking trail right outside the entrance of the lodging area that we got to use. This is for sure a place I would stay at again!"
United States
Samantha B.
The price is HK$503
HK$1,585 total
includes taxes & fees
31 Aug - 1 Sept
Snuggle Up in our Teddy Cottage! *New Listing*
Smart TV

19. The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.6 out of 10, Exceptional, (29 reviews)
"I love this little cabin! Will definitely book again in the future."
United States
Brian M.
The price is HK$431
HK$1,411 total
includes taxes & fees
13 Sept - 14 Sept
The Cabin in Tracy City
Coffee/tea maker, fridge, microwave, oven

20. With Trailhead to One of TN's Tallest Waterfalls

With Trailhead to One of TN's Tallest Waterfalls
Monteagle
9.4 out of 10, Exceptional, (10 reviews)
"Lovely - so enjoyed our stay! So peaceful. "
United States
Elizabeth
The price is HK$619
HK$1,657 total
includes taxes & fees
31 Aug - 1 Sept
With Trailhead to One of TN's Tallest Waterfalls
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

10/10 Excellent
"This is our 3rd time to stay here. We love the location."
Cheri J. 3-night trip
Posted 10 days ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

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:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

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

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Twin Creeks Marina, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffee shops during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Private dock/gazebo on quiet cove. Tims Ford Lake!: This highly rated holiday home rental in Winchester is located on a lake, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 holiday rentals are there in Winchester?

Expedia has 113 holiday 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.