Winchester Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

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, (12 reviews)
"Great location on the square with plenty of dining options a short walk away."
United States
possible Amanda H
The price is ￥14,707
￥29,852 total
includes taxes & fees
May 19 - May 20
Oasis on the Square
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.
The price is ￥15,965
￥32,775 total
includes taxes & fees
May 26 - May 27
Tiny Home w/ RV Hookups
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, (31 reviews)
"Clean, comfortable and 3 bathrooms are a blessing!"
United States
julie c.
The price is ￥17,422
￥55,699 total
includes taxes & fees
May 17 - May 18
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.
Interior

Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.8 out of 10, Exceptional, (13 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
The price is ￥16,392
￥32,087 total
includes taxes & fees
Jun 8 - Jun 9
Winchester's Premier Downtown Loft!
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, (21 reviews)
"Very cozy and great lake location. We definitely plan to go back."
United States
Jason G.
The price is ￥43,555
￥82,911 total
includes taxes & fees
May 17 - May 18
"The Hawk Nest" cabin on Tims Ford Lake
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 ￥11,879
￥30,519 total
includes taxes & fees
May 17 - May 18
Beautifully Renovated Studio 2 miles from the Marina
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 ￥15,838
￥50,880 total
includes taxes & fees
May 21 - May 22
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
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 ￥51,030
￥118,337 total
includes taxes & fees
May 18 - May 19
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 ￥47,039
￥120,538 total
includes taxes & fees
May 17 - May 18
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 ￥47,463
￥109,972 total
includes taxes & fees
May 17 - May 18
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, (79 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 ￥85,525
￥173,663 total
includes taxes & fees
May 17 - May 18
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.
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, (17 reviews)
"Awesome lake house!! A great retreat. Will come back someday we hope!! "
United States
Tara C.
The price is ￥129,238
￥209,077 total
includes taxes & fees
Jun 7 - Jun 8
Lakefront Lodge on Tims Ford Lake
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.
The price is ￥55,433
￥121,012 total
includes taxes & fees
Jun 3 - Jun 4
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, (21 reviews)
"Nice, relaxing. "
United States
Lissette A.
The price is ￥14,112
￥36,250 total
includes taxes & fees
May 24 - May 25
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Free WiFi, bed sheets

Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
8.8 out of 10, Excellent, (3 reviews)
"loved the place and area, only issue was it did seem like it wasn’t properly cleaned before we arrived and found someone’s socks under the pull out couch. But overall everything else was great! "
United States
Mayumi
The price is ￥14,745
￥16,920 total
includes taxes & fees
May 17 - May 18
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
The price is ￥11,879
￥28,509 total
includes taxes & fees
May 18 - May 19
Deciduous Dreams in Deer Lick Falls
Exterior

Smarter than the Average Stay at the Yogi Cottage!

Smarter than the Average Stay at the Yogi Cottage!
Monteagle
9.0 out of 10, Wonderful, (7 reviews)
"We had the best time. The place was really nice. We loved the bear statues that decorated the establishment. Communication was good. Interior was visually appealing."
United States
Shanna R.
The price is ￥10,168
￥30,430 total
includes taxes & fees
May 17 - May 18
Smarter than the Average Stay at the Yogi Cottage!
Fireplace

The Little Village at The Retreat at Water's Edge

The Little Village at The Retreat at Water's Edge
Tracy City
9.6 out of 10, Exceptional, (9 reviews)
"Very nice spot. We would definitely stay again.Our Host was great!"
United States
Kim C.
The price is ￥14,270
￥52,615 total
includes taxes & fees
May 19 - May 20
The Little Village at The Retreat at Water's Edge
Fridge, microwave, oven, stovetop

The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.8 out of 10, Exceptional, (21 reviews)
"Well made cabin, very cute and cozy! Would definitely stay again"
United States
Laura
The price is ￥8,711
￥25,341 total
includes taxes & fees
May 27 - May 28
The Cabin in Tracy City
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

Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

4/10 Poor
"I thought the place was excellent but did not check the sheets. This morning flipped the sheets back and there was dried blood on the sheets!!!! Not mine at all. Almost made me vomit."
Kathryn 1-night trip
Posted 6 hours ago
Microtel Inn & Suites by Wyndham Manchester

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?

Lg lakefront family home with a covered dock and jet-ski port! Nicely remodeled!: Visitors like this Winchester vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Some other top choices in Winchester are Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK and New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks.

How many vacation rentals are there in Winchester?

Expedia has 118 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.