Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

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 AU$286
includes taxes & fees
28 June - 29 June
Winchester's Premier Downtown Loft!

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 AU$280
includes taxes & fees
5 July - 6 July
Oasis on the Square

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)
"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 AU$315
includes taxes & fees
6 July - 7 July
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

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 AU$518
includes taxes & fees
29 June - 30 June
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.

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 AU$277
includes taxes & fees
16 June - 17 June
Beautifully Renovated Studio 2 miles from the Marina

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 AU$510
includes taxes & fees
16 June - 17 June
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

"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 AU$737
includes taxes & fees
20 June - 21 June
"The Hawk Nest" cabin on Tims Ford Lake

The Lakefront Getaway

The Lakefront Getaway
Winchester
9.6 out of 10, Exceptional, (5 reviews)
"Incredible "
United States
Jim C.
The price is AU$664
includes taxes & fees
17 June - 18 June
The Lakefront Getaway

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 AU$1,088
includes taxes & fees
10 June - 11 June
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

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 AU$1,990
includes taxes & fees
15 June - 16 June
Lakefront Lodge on Tims Ford Lake

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 AU$1,675
includes taxes & fees
29 June - 30 June
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

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, (80 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 AU$1,559
includes taxes & fees
13 June - 14 June
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

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 AU$330
includes taxes & fees
15 June - 16 June
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24

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 AU$178
includes taxes & fees
14 June - 15 June
Sasquatch Farm

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 AU$298
includes taxes & fees
17 June - 18 June
Story-time Stay at Our Rupert Cottage!

Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.0 out of 10, Wonderful, (10 reviews)
"Super clean, great location and spacious! "
United States
Karen W.
The price is AU$250
includes taxes & fees
15 June - 16 June
Hiker's Hangout Monteagle

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 AU$231
includes taxes & fees
15 June - 16 June
The Cabin in Tracy City

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 AU$266
includes taxes & fees
10 June - 11 June
With Trailhead to One of TN's Tallest Waterfalls

Lakes, Whiskey & More! Charming Home in Tullahoma

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is AU$484
includes taxes & fees
17 June - 18 June
Lakes, Whiskey & More! Charming Home in Tullahoma

Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
10.0 out of 10, Exceptional, (2 reviews)
"Clean room and a nice quick getaway "
United States
Shaletia T.
The price is AU$145
includes taxes & fees
10 June - 11 June
Boutique Suite in Historic 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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Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$510 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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. 

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.