Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winchester vacation rentals

Outdoor dining

"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.4 out of 10, Exceptional, (19 reviews)
"Very cozy and great lake location. We definitely plan to go back."
United States
Jason G.
$268 nightly
The price is $307
Mar 24 - Mar 25
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
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
9.4 out of 10, Exceptional, (30 reviews)
"Clean, comfortable and 3 bathrooms are a blessing!"
United States
julie c.
$307 nightly
The price is $323
Mar 25 - Mar 26
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.
Fridge, microwave, oven, stovetop

Oasis on the Square

Oasis on the Square
Winchester
9.8 out of 10, Exceptional, (12 reviews)
"Great love the location "
United States
Zita L.
$173 nightly
The price is $187
Mar 26 - Mar 27
Total with taxes and fees
Oasis on the Square
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)
"Great place - quite and relaxing, close to town. The hosts were wonderful, very responsive to any messages and questions! Will definitely return!!"
United States
Theresa A.
$298 nightly
The price is $312
Mar 24 - Mar 25
Total with taxes and fees
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
Microwave, oven, stovetop, dishwasher

Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups
Winchester
9.0 out of 10, Wonderful, (9 reviews)
"Great place to stay! "
United States
Erica P.
$187 nightly
The price is $214
Apr 19 - Apr 20
Total with taxes and fees
Tiny Home w/ RV Hookups
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
$180 nightly
The price is $191
Mar 25 - Mar 26
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
9.8 out of 10, Exceptional, (11 reviews)
"We thoroughly enjoyed our stay in this comfortable and beautiful apartment, right in the heart of Winchester. It’s walkable to several restaurants and a great ice cream shop. Check-in and communication were smooth. "
United States
Jennifer M.
$154 nightly
The price is $166
Mar 24 - Mar 25
Total with taxes and fees
Winchester's Premier Downtown Loft!
Smart TV, fireplace

Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
Winchester
8.0 out of 10, Very Good, (2 reviews)
"This property was perfect for our family and is very close to the marina. Would definitely stay again! "
United States
Emily C.
$158 nightly
The price is $181
Mar 24 - Mar 25
Total with taxes and fees
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
Terrace/patio

Gather at Tims Ford Lake

Gather at Tims Ford Lake
Winchester
9.6 out of 10, Exceptional, (19 reviews)
"Great house for our family. We enjoyed our week at the lake!"
United States
Debra G.
$593 nightly
The price is $679
Mar 24 - Mar 25
Total with taxes and fees
Gather at Tims Ford Lake
Interior

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, (5 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
Mar 24 - Mar 25
Total with taxes and fees
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
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, (35 reviews)
"Great property!"
United States
Greg B.
$610 nightly
The price is $697
Mar 24 - Mar 25
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
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
9.8 out of 10, Exceptional, (78 reviews)
"Excellent host as always...this is our 3rd year spending Thanksgiving at this property...excellent property, well furnished home and excellent host!"
United States
Amy F.
$960 nightly
The price is $1,097
Mar 24 - Mar 25
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (14 reviews)
"Awesome lake house!! A great retreat. Will come back someday we hope!! "
United States
Tara C.
$752 nightly
The price is $859
Mar 28 - Mar 29
Total with taxes and fees
Lakefront Lodge on Tims Ford Lake
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
Apr 2 - Apr 3
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, (23 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.
$839 nightly
The price is $958
Mar 30 - Mar 31
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Smart TV, books

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, (20 reviews)
"To be honest, i was a little uncertain when i booked but a fenced yard was needed. We were all pleasantly surprised. Super cute with excellent amenities. Efficient use of space with everything we could need. Very clean and comfortable. The large fenced yard was a perfect too. "
United States
Connie K.
$207 nightly
The price is $237
Apr 14 - Apr 15
Total with taxes and fees
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Terrace/patio

Flat Branch Lodge - Tracy City, TN

Flat Branch Lodge - Tracy City, TN
Tracy City
9.8 out of 10, Exceptional, (16 reviews)
"Just a lovely stay enjoyed every moment "
United States
Justin D.
$179 nightly
The price is $179
Mar 24 - Mar 25
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.
$156 nightly
The price is $169
Mar 24 - Mar 25
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
Smart TV, fireplace, DVD player

Deciduous Dreams in Deer Lick Falls

Deciduous Dreams in Deer Lick Falls
Monteagle
9.0 out of 10, Wonderful, (7 reviews)
"The cabin had a gorgeous outdoor space making the tiny house seem bigger. Nice kitchen and washer dryer. Super cozy. Clean. Would stay again. "
United States
Victoria W.
$169 nightly
The price is $169
Mar 24 - Mar 25
Total with taxes and fees
Deciduous Dreams in Deer Lick Falls
Interior

Blue Ridge Retreat at The Retreat at Deer Lick Falls

Blue Ridge Retreat at The Retreat at Deer Lick Falls
Monteagle
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful and very comfortable house!!!"
United States
Marie E.
$375 nightly
The price is $422
Mar 24 - Mar 25
Total with taxes and fees
Blue Ridge Retreat 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

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

10/10 Excellent
"Hotel was wonderful. Very clean rooms. Breakfast was excellent. "
Toni 1-night trip
Posted 5 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 $66 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?

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak: Visitors like this Winchester vacation home rental. It is located on a lake and has a fireplace, an arcade game room, 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. Some other top choices in Winchester are Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks, and New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks.

How many vacation rentals are there in Winchester?

Expedia has 111 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 Bear Trace Golf Course.

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.