Winchester Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Winchester holiday rentals

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.
Tiny Home w/ RV Hookups
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 traveller
The price is HK$588
HK$1,494 total
includes taxes & fees
7 Jun - 8 Jun
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, (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 HK$811
HK$1,588 total
includes taxes & fees
8 Jun - 9 Jun
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
7.2 out of 10, Good, (5 reviews)
"Our host did not contact us with instructions. We got there and didnt know where our unit was, how to enter, where the keys were. We were able to get a contact number from the visitor center, but she didnt answer. Poor communication from host. No creamer or sugar to make cofee. Thankfully there was a very nice bath house on premise as ours was very small and the when we flushed the toulet the smell ran us out."
United States
Delon W.
The price is HK$769
HK$1,415 total
includes taxes & fees
8 Jun - 9 Jun
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
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
The price is HK$769
HK$1,515 total
includes taxes & fees
15 Jun - 16 Jun
Oasis on the Square
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.
The price is HK$1,152
HK$3,017 total
includes taxes & fees
30 Jun - 1 Jul
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.
The price is HK$1,089
HK$2,883 total
includes taxes & fees
30 Jun - 1 Jul
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
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)
"Very nice! "
United States
Adam H.
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
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)
"We loved the cabin and we want to stay again soon. "
United States
crystal F.
The price is HK$2,155
HK$4,071 total
includes taxes & fees
20 Jun - 21 Jun
"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, (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.
The price is HK$2,328
HK$6,011 total
includes taxes & fees
7 Jun - 8 Jun
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Dining

The Lakefront Getaway

The Lakefront Getaway
Winchester
9.6 out of 10, Exceptional, (5 reviews)
"Incredible "
United States
Jim C.
The price is HK$1,728
HK$4,885 total
includes taxes & fees
7 Jun - 8 Jun
The Lakefront Getaway
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 HK$3,407
HK$6,323 total
includes taxes & fees
16 Jun - 17 Jun
Lakefront Lodge on Tims Ford Lake
Smart TV, fireplace

Water's Edge - Lakeside retreat

Water's Edge - Lakeside retreat
Winchester
The price is HK$2,298
HK$6,375 total
includes taxes & fees
18 Jun - 19 Jun
Water's Edge - Lakeside retreat
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 HK$5,502
HK$9,421 total
includes taxes & fees
29 Jun - 30 Jun
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
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)
"Host was great. The place is perfect location to Sewanee. "
United States
Emery B.
The price is HK$698
HK$1,786 total
includes taxes & fees
9 Jun - 10 Jun
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 HK$882
HK$1,012 total
includes taxes & fees
5 Jun - 6 Jun
Sasquatch Farm
Fridge, microwave, oven, stovetop

With Trailhead to One of TN's Tallest Waterfalls

With Trailhead to One of TN's Tallest Waterfalls
Monteagle
9.4 out of 10, Exceptional, (6 reviews)
"Lovely - so enjoyed our stay! So peaceful. "
United States
Elizabeth
The price is HK$611
HK$1,434 total
includes taxes & fees
7 Jun - 8 Jun
With Trailhead to One of TN's Tallest Waterfalls
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 HK$588
HK$1,411 total
includes taxes & fees
7 Jun - 8 Jun
Deciduous Dreams in Deer Lick Falls
Terrace/patio

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 HK$503
HK$1,498 total
includes taxes & fees
29 Jun - 30 Jun
Smarter than the Average Stay at the Yogi Cottage!
Smart TV

The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.8 out of 10, Exceptional, (22 reviews)
"Well made cabin, very cute and cozy! Would definitely stay again"
United States
Laura
The price is HK$431
HK$1,254 total
includes taxes & fees
7 Jun - 8 Jun
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"Nice clean room. Close to pool. Enjoyed the corn hole court. Easy to find."
James 1-night trip
Posted 2 hours 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 holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Twin Creeks Marina, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffee shops during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!: This highly rated holiday home rental in Winchester 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Some other top choices in Winchester are Reflection Bay-Dock, Hot Tub, Kayaks and Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family.

How many holiday rentals are there in Winchester?

Expedia has 116 holiday 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.