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 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
$188 nightly
The price is $204
Sep 7 - Sep 8
Total with taxes and fees
Winchester's Premier Downtown Loft!
Interior

2. 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.
$682 nightly
The price is $809
Sep 7 - Sep 8
Total with taxes and fees
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Private kitchen

3. 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
$180 nightly
The price is $195
Sep 7 - Sep 8
Total with taxes and fees
Oasis on the Square
Living area

4. 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 13 - Sep 14
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Outdoor dining

5. "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.
$454 nightly
The price is $519
Sep 6 - Sep 7
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
Exterior

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
$600 nightly
The price is $628
Sep 7 - Sep 8
Total with taxes and fees
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Outdoor dining

7. 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 13 - Sep 14
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

8. 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 9 - Sep 10
Total with taxes and fees
Lakefront Lodge on Tims Ford Lake
Private kitchen

9. 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.
$184 nightly
The price is $210
Sep 8 - Sep 9
Total with taxes and fees
Tiny Home w/ RV Hookups
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 14 - Sep 15
Total with taxes and fees
Cove Sweet Cove! Fire pit, Fishing, Lake Fun!
Outdoor dining

11. 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.
$141 nightly
The price is $160
Sep 20 - Sep 21
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
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.
$725 nightly
The price is $828
Sep 8 - Sep 9
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Living area

13. 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.
$199 nightly
The price is $228
Sep 6 - Sep 7
Total with taxes and fees
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Outdoor dining

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, (165 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.
$145 nightly
The price is $165
Sep 7 - Sep 8
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin
Living area

15. On the University of the South campus, Sewanee, TN.

On the University of the South campus, Sewanee, TN.
Sewanee
9.8 out of 10, Exceptional, (32 reviews)
"wonderful place to stay right on Sewanee's campus!"
United States
katherine v.
$559 nightly
The price is $638
Sep 9 - Sep 10
Total with taxes and fees
On the University of the South campus, Sewanee, TN.
Room

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
$150 nightly
The price is $172
Sep 7 - Sep 8
Total with taxes and fees
Sasquatch Farm
Property grounds

17. Private Multi Family Retreat on 5 Acres!

Private Multi Family Retreat on 5 Acres!
Sewanee
10.0 out of 10, Exceptional, (14 reviews)
"This was a beautiful and very clean house for several generations to stay during Sewanee graduation. It is in a beautiful wooded location very close to Sewanee. The kitchen is well stocked and there are lots of spots to relax on porches. The property is divided up into several separate suite areas, so everyone had their privacy."
United States
Ann K.
$1,108 nightly
The price is $1,193
Sep 7 - Sep 8
Total with taxes and fees
Private Multi Family Retreat on 5 Acres!
Property grounds

18. 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.
$276 nightly
The price is $305
Sep 11 - Sep 12
Total with taxes and fees
The Woods at The Retreat at Deer Lick Falls
Living area

19. Settle Down on the Lake – Your Waterfront Escape in Tracy City

Settle Down on the Lake – Your Waterfront Escape in Tracy City
Tracy City
10.0 out of 10, Exceptional, (13 reviews)
"Quiet and beautiful setting for a girls weekend"
United States
Meaghan D.
$366 nightly
The price is $429
Sep 6 - Sep 7
Total with taxes and fees
Settle Down on the Lake – Your Waterfront Escape in Tracy City
Exterior

20. Hillside Haven at The Retreat at Water's Edge

Hillside Haven at The Retreat at Water's Edge
Tracy City
10.0 out of 10, Exceptional, (39 reviews)
"Great place and location"
United States
Ajit K.
$361 nightly
The price is $414
Sep 13 - Sep 14
Total with taxes and fees
Hillside Haven at The Retreat at Water's Edge
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

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 2 weeks ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

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 $1,097 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?

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 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.