Winchester Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Winchester holiday rentals

Microwave, oven, stovetop, dishwasher

Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups
Winchester
8.8 out of 10, Excellent, (10 reviews)
"The home had everything needed for our three day stay. Location was wonderful as well."
United States
Michael G.
The price is HK$606
HK$1,408 total
includes taxes & fees
20 Apr - 21 Apr
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
9.4 out of 10, Exceptional, (30 reviews)
"Clean, comfortable and 3 bathrooms are a blessing!"
United States
julie c.
The price is HK$862
HK$2,575 total
includes taxes & fees
17 Apr - 18 Apr
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 location on the square with plenty of dining options a short walk away."
United States
possible Amanda H
The price is HK$768
HK$1,515 total
includes taxes & fees
19 Apr - 20 Apr
Oasis on the Square
Interior

Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.8 out of 10, Exceptional, (12 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 HK$811
HK$1,564 total
includes taxes & fees
19 Apr - 20 Apr
Winchester's Premier Downtown Loft!
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 traveller
The price is HK$588
HK$1,494 total
includes taxes & fees
19 Apr - 20 Apr
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.
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
9.4 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 HK$2,154
HK$4,069 total
includes taxes & fees
17 Apr - 18 Apr
"The Hawk Nest" cabin on Tims Ford Lake
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 HK$768
HK$1,414 total
includes taxes & fees
17 Apr - 18 Apr
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 HK$2,341
HK$5,609 total
includes taxes & fees
20 Apr - 21 Apr
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 HK$2,327
HK$6,009 total
includes taxes & fees
17 Apr - 18 Apr
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 HK$2,342
HK$5,458 total
includes taxes & fees
19 Apr - 20 Apr
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Terrace/patio

Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (16 reviews)
"Awesome lake house!! A great retreat. Will come back someday we hope!! "
United States
Tara C.
The price is HK$2,855
HK$5,775 total
includes taxes & fees
20 Apr - 21 Apr
Lakefront Lodge on Tims Ford Lake
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 HK$4,230
HK$8,589 total
includes taxes & fees
19 Apr - 20 Apr
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 price is HK$4,576
HK$8,210 total
includes taxes & fees
7 May - 8 May
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Smart TV, ping pong

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 HK$776
HK$1,907 total
includes taxes & fees
11 May - 12 May
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Smart TV

The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.6 out of 10, Exceptional, (19 reviews)
"Well made cabin, very cute and cozy! Would definitely stay again"
United States
Laura
The price is HK$431
HK$1,253 total
includes taxes & fees
22 Apr - 23 Apr
The Cabin in Tracy City
Terrace/patio

Flat Branch Lodge - Tracy City, TN

Flat Branch Lodge - Tracy City, TN
Tracy City
9.6 out of 10, Exceptional, (18 reviews)
"Just a lovely stay enjoyed every moment "
United States
Justin D.
The price is HK$517
HK$1,457 total
includes taxes & fees
28 Apr - 29 Apr
Flat Branch Lodge - Tracy City, TN
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 HK$564
HK$1,387 total
includes taxes & fees
29 Apr - 30 Apr
Deciduous Dreams in Deer Lick Falls
Exterior

Chic 2BR Cabin D by MHM Luxury Properties

Chic 2BR Cabin D by MHM Luxury Properties
Jasper
9.8 out of 10, Exceptional, (15 reviews)
"Wonderful birthday getaway! The home was lovely along with the nice amenities Jasper Highlands offers its homeowners. Looking forward to staying again!"
United States
Anonymous traveller
The price is HK$535
HK$2,172 total
includes taxes & fees
19 Apr - 20 Apr
Chic 2BR Cabin D by MHM Luxury Properties
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
"It is adequate"
paul 2-night trip
Posted 4 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
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • 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?

Reflection Bay-Dock, Hot Tub, Kayaks: This highly rated holiday home rental in Winchester is located on a lake, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a pool table and 1 hot tub. Some other top choices in Winchester are New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks and Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK.

How many holiday rentals are there in Winchester?

Expedia has 113 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.