Winchester Vacation Rentals

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Nov 13 - Nov 14
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Nov 14 - Nov 15
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Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Winchester

Smart TV, fireplace
Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Winchester
10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay. The home was great! Everything you need. Love the location. Close to Winchester and the lake. Highly recommend. Already planning to stay there again."
United States
Gary W.
$413 nightly
The price is $464
Nov 18 - Nov 19
Total with taxes and fees
Luxurious Lakefront Home- Marina, Boats, and Kayaks!
Dining
Oasis on the Square

Oasis on the Square

Winchester
9.6 out of 10, Exceptional, (9)
"Great accommodations in downtown Winchester! "
United States
LeBron F.
$135 nightly
The price is $143
Nov 16 - Nov 17
Total with taxes and fees
Oasis on the Square
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)
"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
$181 nightly
The price is $192
Nov 14 - Nov 15
Total with taxes and fees
Beautifully Renovated Studio 2 miles from the Marina
TV, fireplace
Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!

Winchester
9.6 out of 10, Exceptional, (9)
"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.
$135 nightly
The price is $143
Nov 16 - Nov 17
Total with taxes and fees
Winchester's Premier Downtown Loft!
Exterior
Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups

Winchester
8.8 out of 10, Excellent, (8)
"Very clean highly recommend if you are looking to get away and relax "
United States
Jeffrey
$219 nightly
The price is $251
Nov 15 - Nov 16
Total with taxes and fees
Tiny Home w/ RV Hookups
Fridge, microwave, oven, stovetop
Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!

Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!

Winchester
9.8 out of 10, Exceptional, (12)
"Property was just as stated. Owners were very accommodating. Great peaceful wooded area. Everything you could possibly want!"
United States
Chris
$305 nightly
The price is $349
Nov 16 - Nov 17
Total with taxes and fees
Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!
Interior
Beautiful And Spacious Fully Renovated Farmhouse

Beautiful And Spacious Fully Renovated Farmhouse

Winchester
9.4 out of 10, Exceptional, (29)
"It was spacious and great for a family event. It really just needed a better cleaning job between guests or maybe it sat empty awhile. We had to wash sheets and towels before we used. Other than that it was very nice. "
United States
Marguerite
$333 nightly
The price is $350
Nov 20 - Nov 21
Total with taxes and fees
Beautiful And Spacious Fully Renovated Farmhouse
Interior
Gorgeous Renovated Home with Open Floor Plan and Large Lot

Gorgeous Renovated Home with Open Floor Plan and Large Lot

Winchester
9.0 out of 10, Wonderful, (16)
"Great potential for outside features (firepits, grills, yard games)."
United States
Darrin S.
$327 nightly
The price is $343
Nov 15 - Nov 16
Total with taxes and fees
Gorgeous Renovated Home with Open Floor Plan and Large Lot
Smart TV, fireplace
The Lakeside Getaway

The Lakeside Getaway

2.0 star property
Winchester
9.6 out of 10, Exceptional, (5)
"We had a great time and the home provided plenty of room for our large group. The only thing I would say would be to rename the property and change a few photos. The impression was given that the property is lakeside, which it is not."
United States
angela s.
$405 nightly
The price is $456
Dec 1 - Dec 2
Total with taxes and fees
The Lakeside Getaway
Terrace/patio
Lakeview Luxe - Lake Access + Pool

Lakeview Luxe - Lake Access + Pool

2.0 star property
Winchester
10.0 out of 10, Exceptional, (3)
"Beautiful home. Very well kept. Hosts were very helpful. Short distance from restaurants and town square. "
United States
Tressa K.
$514 nightly
The price is $581
Nov 16 - Nov 17
Total with taxes and fees
Lakeview Luxe - Lake Access + Pool
Outdoor dining
"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake

Winchester
9.6 out of 10, Exceptional, (18)
"This was a nice and very unique place to stay. We really appreciated that we had a place to dock the boat. "
United States
Dawn D. C.
$455 nightly
The price is $520
Nov 14 - Nov 15
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
Outdoor dining
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

Winchester
$158 nightly
The price is $181
Nov 14 - Nov 15
Total with taxes and fees
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
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

2.0 star property
Winchester
10.0 out of 10, Exceptional, (4)
"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "
United States
Gwen K.
$623 nightly
The price is $701
Nov 14 - Nov 15
Total with taxes and fees
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Terrace/patio
Gather at Tims Ford Lake

Gather at Tims Ford Lake

Winchester
9.6 out of 10, Exceptional, (19)
"Great time nice and quiet"
United States
David C.
$1,829 nightly
The price is $2,090
Nov 17 - Nov 18
Total with taxes and fees
Gather at Tims Ford Lake
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, (34)
"We had a great time gathering for my sister's birthday with family! Love this place will come back again!"
United States
Merideth H.
$546 nightly
The price is $625
Nov 19 - Nov 20
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Property grounds
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

2.0 star property
Winchester
10.0 out of 10, Exceptional, (1)
"Very clean, many extras in the house. Nice location, close to Winchester and the marina. We all enjoyed it from 11 years old, teenagers to adults."
United States
Greg S.
$434 nightly
The price is $488
Nov 16 - Nov 17
Total with taxes and fees
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.
Terrace/patio
Lakefront Luxury on Tims Ford Lake

Lakefront Luxury on Tims Ford Lake

Winchester
10.0 out of 10, Exceptional, (10)
"Very relaxing stay in a quiet neighborhood on the lake. The house is very nice and as advertised. Owner is very communicative and helpful."
United States
Clay W.
$714 nightly
The price is $815
Nov 16 - Nov 17
Total with taxes and fees
Lakefront Luxury on Tims Ford Lake
Marina
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)
"We had our three kids who all brought a friend and this house worked perfectly. The teenage boys took the downstairs as their sleeping and handout spot. We loved the porch and covered deck over looking the water. It’s a further walk than we had thought to the marina but that was fine for us. We will be back!"
United States
Ann Marie S.
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Property grounds
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,

Lake View Prime Location, Community Dock w swim ladders, covered boat slip,

Winchester
10.0 out of 10, Exceptional, (22)
"We were mesmerized when we walked through the doors of the beautiful home! There were 3 different levels of living areas, perfect for our family Thanksgiving! The owner was very attentive and responsive. I don’t think I’ve ever had a better time!"
United States
Cindy L.
$518 nightly
The price is $593
Nov 18 - Nov 19
Total with taxes and fees
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,
Smart TV
The Cabin in Tracy City

The Cabin in Tracy City

Tracy City
10.0 out of 10, Exceptional, (11)
"This is a great cabin for a couple, or a couple with one or two children. The cabin is very clean, well stocked, and everything seems new. We loved hanging out on the back porch swing. It sits back off the road, and you have a lot of privacy. The kitchen was well stocked. No complaints. It fully met our needs for a weekend of hiking and the outdoors. "
United States
Stephen F.
$171 nightly
The price is $171
Nov 14 - Nov 15
Total with taxes and fees
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

Best Western Shelbyville Inn and Suites Celebration Inn

Best Western Shelbyville Inn and Suites Celebration Inn

10/10 Excellent
"Check in was easy & fast. Very courteous. "
Rhonda 2-night trip
Posted 21 hours ago
Best Western Shelbyville Inn and Suites Celebration Inn

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

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

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Hook, Wine, & Sinker-Sleeps 28, Dock, Hot Tub, Kayaks/SUPs: Visitors like this Winchester vacation home rental. It is located on a lake and has a balcony, an arcade game room, and a barbecue grill to put you at ease in your new surroundings. It has 6 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 hot tub in this rental home to help you unwind. Some other top choices in Winchester are Beautiful Lake Views at Twin Creeks! and Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak.

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 Harvey's Garden and Tims Ford are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tims Ford State Park and Tims Ford Lake.

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.