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.
The price is ￥17,374
￥48,536 total
includes taxes & fees
Mar 29 - Mar 30
"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.
The price is ￥17,456
￥52,634 total
includes taxes & fees
Apr 15 - Apr 16
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.
The price is ￥15,636
￥30,819 total
includes taxes & fees
Apr 12 - Apr 13
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.
The price is ￥15,939
￥49,610 total
includes taxes & fees
Mar 29 - Mar 30
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.
The price is ￥18,967
￥36,355 total
includes taxes & fees
Apr 11 - Apr 12
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
The price is ￥11,954
￥30,394 total
includes taxes & fees
Mar 29 - Mar 30
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.
The price is ￥16,497
￥31,814 total
includes taxes & fees
Apr 26 - Apr 27
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.
The price is ￥15,636
￥28,778 total
includes taxes & fees
Apr 7 - Apr 8
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.
The price is ￥41,888
￥106,655 total
includes taxes & fees
Mar 30 - Mar 31
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.
The price is ￥47,339
￥122,263 total
includes taxes & fees
Mar 27 - Mar 28
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.
The price is ￥47,658
￥111,060 total
includes taxes & fees
Apr 5 - Apr 6
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.
The price is ￥86,071
￥174,772 total
includes taxes & fees
Mar 27 - Mar 28
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.
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.
The price is ￥92,691
￥166,310 total
includes taxes & fees
Apr 19 - Apr 20
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.
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)
"Nice, relaxing. "
United States
Lissette A.
The price is ￥15,710
￥37,671 total
includes taxes & fees
Apr 21 - Apr 22
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.
The price is ￥9,563
￥28,690 total
includes taxes & fees
Mar 30 - Mar 31
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.
The price is ￥10,188
￥26,884 total
includes taxes & fees
Mar 29 - Mar 30
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, (8 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
The price is ￥12,751
￥29,487 total
includes taxes & fees
Apr 26 - Apr 27
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.
The price is ￥21,119
￥67,655 total
includes taxes & fees
Apr 1 - Apr 2
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

8/10 Good
"Best pricing, great folks. Room was clean. Needs updated, but a good place to stay."
Jeff 1-night trip
Posted 1 day ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

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 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.