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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation rentals

Interior

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.6 out of 10, Exceptional, (17 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
$172 nightly
The price is $186
Oct 12 - Oct 13
Total with taxes and fees
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
$167 nightly
The price is $181
Oct 11 - Oct 12
Total with taxes and fees
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.
$181 nightly
The price is $207
Sep 15 - Sep 16
Total with taxes and fees
Tiny Home w/ RV Hookups
TV

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
$600 nightly
The price is $628
Sep 14 - Sep 15
Total with taxes and fees
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Outdoor dining

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

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.4 out of 10, Exceptional, (26 reviews)
"Great little, hidden get-away!"
United States
Rich F.
$455 nightly
The price is $520
Sep 14 - Sep 15
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
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.
$159 nightly
The price is $181
Sep 20 - Sep 21
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
Smart TV

7. 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.
$685 nightly
The price is $782
Sep 14 - Sep 15
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Outdoor dining

8. 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.
$960 nightly
The price is $1,097
Sep 14 - Sep 15
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

9. 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.
$1,028 nightly
The price is $1,174
Sep 16 - Sep 17
Total with taxes and fees
Lakefront Lodge on Tims Ford Lake
Private kitchen

10. Cove Sweet Cove! Fire pit, Fishing, Lake Fun!

Cove Sweet Cove! Fire pit, Fishing, Lake Fun!
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Loved our stay, the place was great and super clean. Host was very responsive, would definitely stay here again."
United States
Taylor K.
$931 nightly
The price is $1,063
Sep 15 - Sep 16
Total with taxes and fees
Cove Sweet Cove! Fire pit, Fishing, Lake Fun!
Property grounds

11. 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.
$721 nightly
The price is $824
Sep 14 - Sep 15
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Smart TV, books

12. 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, (25 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.
$192 nightly
The price is $221
Sep 14 - Sep 15
Total with taxes and fees
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
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, (166 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.
$149 nightly
The price is $170
Oct 14 - Oct 15
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin
Children's area

14. 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, (41 reviews)
"The home was cute, clean and quiet. Would be great for a family but I also enjoyed my stay alone. Love the tiny home neighborhood surrounded by nature."
United States
Skip E.
$275 nightly
The price is $304
Sep 15 - Sep 16
Total with taxes and fees
The Woods at The Retreat at Deer Lick Falls
WiFi (free), bed sheets

15. 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
$150 nightly
The price is $172
Sep 14 - Sep 15
Total with taxes and fees
Sasquatch Farm
Smart TV

16. The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.6 out of 10, Exceptional, (30 reviews)
"Great place, clean and quiet!!"
United States
Jose
$160 nightly
The price is $180
Sep 14 - Sep 15
Total with taxes and fees
The Cabin in Tracy City
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, (11 reviews)
"Nice place to stay. Close to the caverns where we saw a show. Property is very clean. Really nice stay."
United States
Dawn
$170 nightly
The price is $191
Sep 14 - Sep 15
Total with taxes and fees
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Coffee/tea maker, fridge, microwave, oven

18. 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, (38 reviews)
"House is kept in great condition, beautiful location, and perfect stay when attending the caverns (12 minutes away)"
United States
Antonio M.
$232 nightly
The price is $261
Sep 14 - Sep 15
Total with taxes and fees
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Outdoor dining

19. 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.
$199 nightly
The price is $213
Sep 15 - Sep 16
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
Exterior detail

20. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
$183 nightly
The price is $206
Sep 14 - Sep 15
Total with taxes and fees
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

Best Western Inn

Best Western Inn

10/10 Excellent
"Great spot for our weekend getaway"
Justin 3-night trip
Posted 6 days ago
Best Western Inn

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $201 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Reflection Bay-Dock, Hot Tub, Kayaks: 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 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a pool table and a hot tub. Some other top choices in Winchester are Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation and Enjoy Your Vacation on Tims Ford Lake.

How many vacation rentals are there in Winchester?

Expedia has 113 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.