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

Winchester Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchester vacation rentals

A modern living room with a built-in aquarium, a leather sofa, and a patterned rug.

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
$167 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
Winchester's Premier Downtown Loft!
A modern living room with a blue sofa, a staircase, a kitchen, and a fireplace.

2. Iconic Winchester home near Tims Ford State Park!

Iconic Winchester home near Tims Ford State Park!
Winchester
$371 nightly
The price is $425
Nov 9 - Nov 10
Total with taxes and fees
Iconic Winchester home near Tims Ford State Park!
A modern kitchen with dark cabinetry, stainless steel appliances, and a light-colored backsplash.

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
$167 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
Oasis on the Square
A kitchen with a coffee machine, a sink, and a window with curtains.

4. *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.
$449 nightly
The price is $464
Nov 8 - Nov 9
Total with taxes and fees
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A spacious kitchen with granite countertops, white cabinetry, and a built-in dishwasher. There are multiple windows providing natural light and a view of the outdoors.

5. 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.
$163 nightly
The price is $189
Nov 16 - Nov 17
Total with taxes and fees
Tiny Home w/ RV Hookups
A marina with boats docked, a dock with a covered area, and a sunset over water.

6. 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
$793 nightly
The price is $907
Nov 10 - Nov 11
Total with taxes and fees
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Dining

7. The Lakeside Getaway

The Lakeside Getaway
Winchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
United States
Jim C.
$349 nightly
The price is $419
Nov 10 - Nov 11
Total with taxes and fees
The Lakeside Getaway
A log cabin with a porch, outdoor seating, and a welcome sign.

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.
$272 nightly
The price is $314
Nov 11 - Nov 12
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
A white RV with 'Campbound' branding parked by a lake with picnic tables and chairs.

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.
$139 nightly
The price is $159
Nov 14 - Nov 15
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
Room

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.
$1,788 nightly
The price is $2,148
Nov 12 - Nov 13
Total with taxes and fees
Luxurious Lakefront Home- Marina, Boats, and Kayaks!
Living area

11. A quiet getaway.

A quiet getaway.
Winchester
$314 nightly
The price is $363
Nov 11 - Nov 12
Total with taxes and fees
A quiet getaway.
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

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.
$744 nightly
The price is $859
Nov 8 - Nov 9
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

13. 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.
$620 nightly
The price is $717
Nov 8 - Nov 9
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A compact RV interior with a kitchenette, a seating area with a sofa and chairs, and a dining table.

14. 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.
$173 nightly
The price is $200
Nov 8 - Nov 9
Total with taxes and fees
Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
A kitchen with a double sink, a microwave, and a window with a view of the outdoors.

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

Cozy camper. Queen bed with bunk beds in tranquil Winchester.
Winchester
$187 nightly
The price is $214
Nov 8 - Nov 9
Total with taxes and fees
Cozy camper. Queen bed with bunk beds in tranquil Winchester.
A compact living space with a kitchenette, a dining area, and a seating area with a sofa.

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

Cozy 2 bed 2 bath camper in Winchester TN.
Winchester
$206 nightly
The price is $236
Nov 8 - Nov 9
Total with taxes and fees
Cozy 2 bed 2 bath camper in Winchester TN.
Living area

17. 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.
$224 nightly
The price is $258
Nov 9 - Nov 10
Total with taxes and fees
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
A red mailbox with "McCormick Farmall" on it, a black barbecue grill, a red metal table and chairs, and a sign that says "Come In We're Open".

18. 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.
$158 nightly
The price is $182
Nov 16 - Nov 17
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin
A spacious interior with wooden beams, a reception desk, and a sign reading "Welcome to the Family."

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.
$170 nightly
The price is $193
Nov 8 - Nov 9
Total with taxes and fees
Whiskey Trails Cottage
A bedroom with a bed, a ceiling fan, a wall-mounted tree decoration, a nightstand with a lamp, and a painting of a sunflower field.

20. SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square

SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square
Lynchburg
9.8 out of 10, Exceptional, (6 reviews)
"Loved are stay here. Great hosts."
United States
Patricia
$109 nightly
The price is $125
Nov 9 - Nov 10
Total with taxes and fees
SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square
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

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

10/10 Excellent
"Clean Room & Great Breakfast"
Barbara Sue 1-night trip
Posted 21 hours ago
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

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 $196 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?

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!: Visitors like this Winchester vacation home rental. It 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 you can cook with friends or family. You can relax into your vacation 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 vacation rentals are there in Winchester?

Expedia has 114 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 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 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.