Winchester Vacation Rentals

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Check prices for these dates

Tonight
Sep 24 - Sep 25
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Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Vacation Rentals in Winchester

Our top choices for Winchester vacation rentals

"The Hawk Nest" cabin on Tims Ford Lake
Outdoor dining

"The Hawk Nest" cabin on Tims Ford Lake

9.6 out of 10, Exceptional, (18)
"We absolutely loved staying here. The owner was very communicative with us.The view and peacefulness was amazing. Close to Winchester if you want to go into town. We truly enjoyed our stay! "
The price is ￥22,009
￥53,473 total
includes taxes & fees
Sep 25 - Sep 26
"The Hawk Nest" cabin on Tims Ford Lake
Reflection Bay-Dock, Hot Tub, Kayaks
Fridge, microwave, oven, stovetop

Reflection Bay-Dock, Hot Tub, Kayaks

10.0 out of 10, Exceptional, (11)
"Great communication and great location "
Reflection Bay-Dock, Hot Tub, Kayaks
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

10.0 out of 10, Exceptional, (74)
"This was our second time staying in this house and I’m sure we will be back. Love how private the dock is and the whole set up of the house. "
The price is ￥59,782
￥135,884 total
includes taxes & fees
Sep 26 - Sep 27
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs
Fridge, microwave, oven, stovetop

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great stay!! Plenty of space. Clean. Great location. "
Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs
Beautiful Lake Views at Twin Creeks!
Smart TV, fireplace, video games, DVD player

Beautiful Lake Views at Twin Creeks!

10.0 out of 10, Exceptional, (56)
"This house has everything! We enjoyed the screened porch each morning with coffee and the lake view. The neighborhood was great for walking the dog. We enjoyed the Bodega close by and the live music at the marina. The town of Winchester is adorable! "
Beautiful Lake Views at Twin Creeks!
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation
Fridge, microwave, oven, stovetop

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

9.6 out of 10, Exceptional, (34)
"We had a wonderful Memorial Day holiday weekend at the lake. The house and location were superb. We will definitely book again. "
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
Marina

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

10.0 out of 10, Exceptional, (49)
"Our family, my two sisters and their family’s both stayed here during our family reunion in Tullahoma. We had the best time! The dock was a favorite spot for all ages 80 to 2 yrs old. Definitely recommend the luxury golf cart, it was a great way to get around. The house was perfect for our 3 family’s everyone enjoyed themselves. Thank you! Can’t wait to come back!"
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
Outdoor dining

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

2.0 star property
10.0 out of 10, Exceptional, (15)
"Everything was perfect. We really enjoyed our stay. "
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak
Private dock/gazebo on quiet cove. Tims Ford Lake!
Exterior

Private dock/gazebo on quiet cove. Tims Ford Lake!

10.0 out of 10, Exceptional, (38)
"The house was very comfortable and clean and the views were beautiful. Eddie communicated with us often and was available whenever we needed him. "
Private dock/gazebo on quiet cove. Tims Ford Lake!
Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village
Fridge, microwave, oven, stovetop

Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village

10.0 out of 10, Exceptional, (3)
"Great location, easy in and out. Thanks John!"
Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc
Fridge, microwave, oven, stovetop

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

10.0 out of 10, Exceptional, (29)
"We had a wonderful stay. We all loved your place. It was very accommodating and we loved the convenience of being in town."
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
3 bedrooms, desk, travel crib, free WiFi

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

10.0 out of 10, Exceptional, (25)
"We had a wonderful time and will definitely be back!!!"
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
Ambassador Inn And Suites
Private kitchen

Ambassador Inn And Suites

3.5 star property
6.4 out of 10, (275)
"Other then their being cockroach’s on everything. It was an ok stay. "
The price is ￥8,588
￥10,330 total
includes taxes & fees
Oct 10 - Oct 11
Ambassador Inn And Suites
Treehouse Getaway w/ Hot Tub & Views!
Outdoor spa tub

Treehouse Getaway w/ Hot Tub & Views!

9.6 out of 10, Exceptional, (10)
"Very impressed with the amenities. Everything needed for a wonderfully cozy stay. Hottub was very clean and perfect temp. Loved the attic sleeping area - very comfy bed. Perfect stay!"
The price is ￥15,510
￥31,770 total
includes taxes & fees
Sep 30 - Oct 1
Treehouse Getaway w/ Hot Tub & Views!
Hummingbird Treehouse Getaway w/ Hot Tub & Firepit
Pool

Hummingbird Treehouse Getaway w/ Hot Tub & Firepit

10.0 out of 10, Exceptional, (363)
"Property was as described. Easy to access and close to hiking and two towns. Would stay here again. "
The price is ￥27,308
￥45,780 total
includes taxes & fees
Oct 2 - Oct 3
Hummingbird Treehouse Getaway w/ Hot Tub & Firepit
Eagle Treehouse Getaway with Hot Tub, Gas Fireplace, and Outdoor Firepit!
Property grounds

Eagle Treehouse Getaway with Hot Tub, Gas Fireplace, and Outdoor Firepit!

10.0 out of 10, Exceptional, (264)
"Close, quite family getaway. "
The price is ￥25,118
￥43,867 total
includes taxes & fees
Sep 30 - Oct 1
Eagle Treehouse Getaway with Hot Tub, Gas Fireplace, and Outdoor Firepit!
Private Off-Grid Cabin on a Bluff
Outdoor dining

Private Off-Grid Cabin on a Bluff

The price is ￥13,152
￥23,973 total
includes taxes & fees
Sep 28 - Sep 29
Private Off-Grid Cabin on a Bluff
Escape to Banjo Bungalow your cozy 2-bdrm lakefront cabin on 27 private acres
Exterior

Escape to Banjo Bungalow your cozy 2-bdrm lakefront cabin on 27 private acres

9.8 out of 10, Exceptional, (143)
"This cute cabin was a beautiful great-a-way that allows one to enjoy nature. A place to get away from the hussle and bussle of life and just relax. "
Escape to Banjo Bungalow your cozy 2-bdrm lakefront cabin on 27 private acres
Rainbows End River Lodge
Exterior

Rainbows End River Lodge

10.0 out of 10, Exceptional, (2)
"Absolutely gorgeous property and all possible amenities needed. Will definitely rent again! "
Rainbows End River Lodge
The Honeysuckle House - Tiny House, BIG Living!
Terrace/patio

The Honeysuckle House - Tiny House, BIG Living!

10.0 out of 10, Exceptional, (20)
"We loved the cabin! Perfect little weekend getaway. "
The price is ￥19,927
￥50,342 total
includes taxes & fees
Oct 3 - Oct 4
The Honeysuckle House - Tiny House, BIG Living!
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

Best Western Shelbyville Inn and Suites Celebration Inn

Best Western Shelbyville Inn and Suites Celebration Inn

10/10 Excellent
"Very good overall . No complaints . "
William 2-night trip
Posted 4 days ago
Best Western Shelbyville Inn and Suites Celebration Inn

Find out more about Winchester

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 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?

Reflection Bay-Dock, Hot Tub, Kayaks: 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 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a pool table and a hot tub. Some other top choices in Winchester are Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs and Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub.

How many vacation rentals are there in Winchester?

Expedia has 117 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.