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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winchester vacation rentals

Fridge, microwave, coffee/tea maker, toaster

Beautifully Renovated Studio 2 miles from the Marina

Beautifully Renovated Studio 2 miles from the Marina
Winchester
9.8 out of 10, Exceptional, (15 reviews)
"The place was exactly as pictured with an easy check-in and out process. Was a perfect little place for us to stay for a long weekend!"
United States
Anonymous traveler
$183 nightly
The price is $194
Jul 20 - Jul 21
Total with taxes and fees
Beautifully Renovated Studio 2 miles from the Marina
Interior

Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.6 out of 10, Exceptional, (14 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
Jul 12 - Jul 13
Total with taxes and fees
Winchester's Premier Downtown Loft!
Smart TV

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
Winchester
8.8 out of 10, Excellent, (21 reviews)
"Peaceful, relaxing and pet friendly great location!"
United States
Holly M.
$319 nightly
The price is $335
Jul 20 - Jul 21
Total with taxes and fees
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
Fridge, microwave, oven, stovetop

Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.

Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.
Winchester
9.6 out of 10, Exceptional, (33 reviews)
"Clean, comfortable and 3 bathrooms are a blessing!"
United States
julie c.
$328 nightly
The price is $344
Jul 27 - Jul 28
Total with taxes and fees
Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.
Microwave, oven, stovetop, dishwasher

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.
$190 nightly
The price is $217
Jul 27 - Jul 28
Total with taxes and fees
Tiny Home w/ RV Hookups
Outdoor dining

Stationary tiny camper in Winchester, TN with pond and mountain views.

Stationary tiny camper in Winchester, TN with pond and mountain views.
Winchester
$141 nightly
The price is $160
Jul 16 - Jul 17
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
Fridge, microwave, oven, stovetop

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
$181 nightly
The price is $196
Jul 12 - Jul 13
Total with taxes and fees
Oasis on the Square
Outdoor dining

"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.2 out of 10, Wonderful, (23 reviews)
"Great little, hidden get-away!"
United States
Rich F.
$286 nightly
The price is $328
Jul 10 - Jul 11
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
Towels, soap, shampoo

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 $767
Jul 10 - Jul 11
Total with taxes and fees
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Smart TV, table tennis

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.
$690 nightly
The price is $788
Aug 5 - Aug 6
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Outdoor dining

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.
$993 nightly
The price is $1,139
Jul 27 - Jul 28
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

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.
$953 nightly
The price is $1,048
Jul 10 - Jul 11
Total with taxes and fees
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Terrace/patio

Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (19 reviews)
"It’s a very beautiful home and the views of the lake are amazing! My husband and I had a small church wedding ceremony in Manchester during our stay, and had our wedding photographer take some pictures of us before the ceremony at this home beforehand! The host is communicative and I would recommend this stay! Would definitely stay again! "
United States
Jenna M.
$1,028 nightly
The price is $1,174
Aug 2 - Aug 3
Total with taxes and fees
Lakefront Lodge on Tims Ford Lake
Property grounds

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, (36 reviews)
"Very nice! "
United States
Adam H.
$725 nightly
The price is $828
Aug 2 - Aug 3
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Smart TV

The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.8 out of 10, Exceptional, (25 reviews)
"The cabin was perfect. Clean with all of the amenities you need for a short stay. Close to The Caverns and great shopping in Monteagle. Highly recommended. "
United States
Leslie G.
$161 nightly
The price is $161
Jul 10 - Jul 11
Total with taxes and fees
The Cabin in Tracy City
Interior

Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, host was very accommodating. Would stay again! Clean accommodations, great location, and very comfortable."
United States
Eric S.
$101 nightly
The price is $101
Jul 12 - Jul 13
Total with taxes and fees
Boutique Suite in Historic Tracy City!
Free WiFi, bed sheets

Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
9.2 out of 10, Wonderful, (7 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
$95 nightly
The price is $109
Jul 12 - Jul 13
Total with taxes and fees
Sasquatch Farm
Smart TV, fireplace, DVD player

Deciduous Dreams in Deer Lick Falls

Deciduous Dreams in Deer Lick Falls
Monteagle
9.4 out of 10, Exceptional, (11 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.
$184 nightly
The price is $184
Jul 12 - Jul 13
Total with taxes and fees
Deciduous Dreams in Deer Lick Falls
Terrace/patio

Flat Branch Lodge - Tracy City, TN

Flat Branch Lodge - Tracy City, TN
Tracy City
9.6 out of 10, Exceptional, (22 reviews)
"Everything was wonderful. Very peaceful setting in the woods which was perfect for my family. We had a great time!"
United States
Samuel
$202 nightly
The price is $202
Jul 29 - Jul 30
Total with taxes and fees
Flat Branch Lodge - Tracy City, TN
Outdoor dining

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.
$195 nightly
The price is $208
Jul 22 - Jul 23
Total with taxes and fees
Story-time Stay at Our Rupert 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

Tim's Ford Lakefront Home

Tim's Ford Lakefront Home

10/10 Excellent
"This home was delightful! The owners were very responsive and kind. The community is precious."
Sherry C. 3-night trip
Posted 9 hours ago
Tim's Ford Lakefront Home

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 $788 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 Spacious Family Gem: Golf Cart - 2 Ensuites - Pool and Private dock/gazebo on quiet cove. Tims Ford Lake!.

How many vacation rentals are there in Winchester?

Expedia has 116 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 Franklin County Farmers Market and Tims Ford State Park.

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.