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

Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

1. 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 NZ$341
includes taxes & fees
9 Aug - 10 Aug
Winchester's Premier Downtown Loft!

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 NZ$329
includes taxes & fees
9 Aug - 10 Aug
Oasis on the Square

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 NZ$298
includes taxes & fees
18 Aug - 19 Aug
Tiny Home w/ RV Hookups

4. 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 NZ$1,185
includes taxes & fees
7 Aug - 8 Aug
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

5. 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 NZ$275
includes taxes & fees
18 Aug - 19 Aug
Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC

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 NZ$252
includes taxes & fees
31 Aug - 1 Sept
Stationary tiny camper in Winchester, TN with pond and mountain views.

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 NZ$756
includes taxes & fees
20 Aug - 21 Aug
"The Hawk Nest" cabin on Tims Ford Lake

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)
"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 NZ$1,177
includes taxes & fees
12 Aug - 13 Aug
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

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 NZ$1,770
includes taxes & fees
3 Sept - 4 Sept
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

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, (81 reviews)
"We had a great time! "
United States
Cindy O.
The price is NZ$1,619
includes taxes & fees
9 Aug - 10 Aug
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

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 NZ$1,734
includes taxes & fees
9 Aug - 10 Aug
Lakefront Lodge on Tims Ford Lake

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 NZ$2,199
includes taxes & fees
31 Aug - 1 Sept
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

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 NZ$1,191
includes taxes & fees
17 Aug - 18 Aug
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

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 NZ$246
includes taxes & fees
1 Sept - 2 Sept
A very rustic converted pole barn unique cozy cabin

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 NZ$246
includes taxes & fees
3 Sept - 4 Sept
Queen ensuite room in historic railroad inn & town. Continental breakfast.

16. 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 NZ$346
includes taxes & fees
26 Aug - 27 Aug
Deciduous Dreams in Deer Lick Falls

17. 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 NZ$167
includes taxes & fees
3 Sept - 4 Sept
Sasquatch Farm

18. The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.6 out of 10, Exceptional, (27 reviews)
"Beautifully decorated, clean cabin. Very comfortable on a beautiful piece of land. Very relaxing and only 15 minute drive to the Caverns!"
United States
Kalindi M.
The price is NZ$308
includes taxes & fees
2 Sept - 3 Sept
The Cabin in Tracy City

19. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is NZ$349
includes taxes & fees
12 Aug - 13 Aug
Whiskey Trails Cottage

20. 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)
The price is NZ$327
includes taxes & fees
25 Aug - 26 Aug
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
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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Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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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 Spacious Family Gem: Golf Cart - 2 Ensuites - Pool.

How many holiday rentals are there in Winchester?

Expedia has 118 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 and Tims Ford Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tims Ford State Park and Elk River.

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.