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

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Our top choices for Winchester holiday rentals

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.6 out of 10, Exceptional, (19 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 £141
includes taxes & fees
9 Nov - 10 Nov
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 £140
includes taxes & fees
9 Nov - 10 Nov
Oasis on the Square

3. Iconic Winchester home near Tims Ford State Park!

Iconic Winchester home near Tims Ford State Park!
Winchester
The price is £349
includes taxes & fees
18 Nov - 19 Nov
Iconic Winchester home near Tims Ford State Park!

4. 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 £680
includes taxes & fees
11 Nov - 12 Nov
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

5. *NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
10.0 out of 10, Exceptional, (1 review)
"This was the perfect place for our family of five to use while visiting University of the South!! We weren’t able to take advantage of the hot tub or kayaks but we did wander the property and take advantage of the beautiful water views.Make sure to visit the Sunrise Cafe while you are there! Order a plate of cinnamon role pancakes for the table!! Delicious."
United States
Vonda R.
The price is £353
includes taxes & fees
8 Nov - 9 Nov
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub

6. 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 £143
includes taxes & fees
19 Nov - 20 Nov
Tiny Home w/ RV Hookups

7. The Lakefront Getaway

The Lakefront Getaway
Winchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
United States
Jim C.
The price is £323
includes taxes & fees
18 Nov - 19 Nov
The Lakefront Getaway

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

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.0 out of 10, Wonderful, (27 reviews)
"Great little, hidden get-away!"
United States
Rich F.
The price is £239
includes taxes & fees
9 Nov - 10 Nov
"The Hawk Nest" cabin on Tims Ford Lake

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 £122
includes taxes & fees
12 Nov - 13 Nov
Stationary tiny camper in Winchester, TN with pond and mountain views.

10. Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Luxurious Lakefront Home- Marina, Boats, and Kayaks!
Winchester
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our stay. The home was great! Everything you need. Love the location. Close to Winchester and the lake. Highly recommend. Already planning to stay there again."
United States
Gary W.
The price is £1,590
includes taxes & fees
19 Nov - 20 Nov
Luxurious Lakefront Home- Marina, Boats, and Kayaks!

11. 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, (27 reviews)
"This property conbined with the unit nexf door worked perfectly for our group of 18 people to enjoy a great 4th of july week at the lake."
United States
Timothy W.
The price is £535
includes taxes & fees
8 Nov - 9 Nov
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

12. 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, (83 reviews)
"We had a great time! "
United States
Cindy O.
The price is £651
includes taxes & fees
11 Nov - 12 Nov
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

13. A quiet getaway.

A quiet getaway.
Winchester
The price is £280
includes taxes & fees
19 Nov - 20 Nov
A quiet getaway.

14. Cozy camper. Queen bed with bunk beds in tranquil Winchester.

Cozy camper. Queen bed with bunk beds in tranquil Winchester.
Winchester
The price is £162
includes taxes & fees
7 Nov - 8 Nov
Cozy camper. Queen bed with bunk beds in tranquil Winchester.

15. Cozy 2 bed 2 bath camper in Winchester TN.

Cozy 2 bed 2 bath camper in Winchester TN.
Winchester
The price is £182
includes taxes & fees
7 Nov - 8 Nov
Cozy 2 bed 2 bath camper in Winchester TN.

16. Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24

Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Sewanee
9.8 out of 10, Exceptional, (28 reviews)
"A great deal and a great location- nice and secluded and close to the caverns where we did a couple shows while visiting. Comfortable spot and wonderful hosts. "
United States
Ryan B.
The price is £184
includes taxes & fees
9 Nov - 10 Nov
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24

17. 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, (169 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 £140
includes taxes & fees
16 Nov - 17 Nov
A very rustic converted pole barn unique cozy cabin

18. 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, (17 reviews)
"This is going to be my go to spot for all Caverns shows. Comfy, spacious and perfect for my crew of 4. The cafe attached was a nice bonus!"
United States
Andrea
The price is £162
includes taxes & fees
9 Nov - 10 Nov
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns

19. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. Had everything we needed. Great location."
United States
Jennifer T.
The price is £150
includes taxes & fees
8 Nov - 9 Nov
Whiskey Trails Cottage

20. The Woods at The Retreat at Deer Lick Falls

The Woods at The Retreat at Deer Lick Falls
Monteagle
9.8 out of 10, Exceptional, (42 reviews)
"Fit the needs for a golf trip away from home. Very charming community in the woods. Place was clean with no issues. Nice loft if you have kids. Would recommend!"
United States
John S.
The price is £216
includes taxes & fees
10 Nov - 11 Nov
The Woods at The Retreat at 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

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, apart-hotels, 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 £151 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?

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!: This highly rated holiday home rental in Winchester is located on a lake, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Some other top choices in Winchester are Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre and Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation.

How many holiday rentals are there in Winchester?

Expedia has 114 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.