High resolution aerial view panorama of lakefront homes, boat docks and beautiful autumn colorful foliage on Tims Ford Lake in Winchester Tennessee USA.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Winchester vacation rentals

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
$178 nightly
The price is $193
Jun 29 - Jun 30
Total with taxes and fees
Oasis on the Square
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
$186 nightly
The price is $202
Jun 28 - Jun 29
Total with taxes and fees
Winchester's Premier Downtown Loft!
1 bedroom, iron/ironing board, WiFi, bed sheets

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
Jun 29 - Jun 30
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
Hair dryer, towels

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
$180 nightly
The price is $191
Jun 23 - Jun 24
Total with taxes and fees
Beautifully Renovated Studio 2 miles from the Marina
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.
$358 nightly
The price is $377
Jul 7 - Jul 8
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.
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, (19 reviews)
"Peaceful, relaxing and pet friendly great location!"
United States
Holly M.
$349 nightly
The price is $368
Jul 7 - Jul 8
Total with taxes and fees
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
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.
$461 nightly
The price is $526
Jun 25 - Jun 26
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
Dining

The Lakeside Getaway

The Lakeside Getaway
Winchester
9.6 out of 10, Exceptional, (5 reviews)
"Incredible "
United States
Jim C.
$399 nightly
The price is $448
Jun 23 - Jun 24
Total with taxes and fees
The Lakeside Getaway
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, (6 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
Jun 23 - Jun 24
Total with taxes and fees
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
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.
$1,088 nightly
The price is $1,202
Jun 29 - Jun 30
Total with taxes and fees
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
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, (24 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.
$944 nightly
The price is $1,080
Jul 1 - Jul 2
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Smart TV

The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.8 out of 10, Exceptional, (22 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.
$160 nightly
The price is $160
Jun 23 - Jun 24
Total with taxes and fees
The Cabin in Tracy City
Free WiFi, bed sheets

Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
9.0 out of 10, Wonderful, (6 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 9 - Jul 10
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
9.2 out of 10, Wonderful, (9 reviews)
"This property was everything and more. Our fur baby loved this trip, there is information about what to do around the area and on the property in a binder inside. This came in handy to locate the trails and amazing waterfall on the grounds. There is a super cute pavilion with outdoor fireplace and fire pit, along with rocking chairs for when the nights start to warm up. Definitely plan on returning. "
United States
Pamela
$180 nightly
The price is $180
Jul 20 - Jul 21
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
$185 nightly
The price is $185
Jun 23 - Jun 24
Total with taxes and fees
Flat Branch Lodge - Tracy City, TN
House (3 Bedrooms) | Interior

Lakes, Whiskey & More! Charming Home in Tullahoma

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
$291 nightly
The price is $341
Jun 27 - Jun 28
Total with taxes and fees
Lakes, Whiskey & More! Charming Home in Tullahoma
Smart TV, fireplace

Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV

Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Monteagle
9.6 out of 10, Exceptional, (9 reviews)
$172 nightly
The price is $172
Jun 29 - Jun 30
Total with taxes and fees
Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Fridge, microwave, oven, stovetop

With Trailhead to One of TN's Tallest Waterfalls

With Trailhead to One of TN's Tallest Waterfalls
Monteagle
9.6 out of 10, Exceptional, (7 reviews)
"Lovely - so enjoyed our stay! So peaceful. "
United States
Elizabeth
$183 nightly
The price is $183
Jun 23 - Jun 24
Total with taxes and fees
With Trailhead to One of TN's Tallest Waterfalls
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.
$192 nightly
The price is $205
Jun 23 - Jun 24
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
Exterior

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.
$291 nightly
The price is $327
Jun 25 - Jun 26
Total with taxes and fees
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

Best Western Inn

Best Western Inn

10/10 Excellent
"Tyler was super helpful!"
Christopher 2-night trip
Posted 3 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 $368 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 Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family.

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 Tims Ford State Park and Franklin County Farmers Market.

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.