A calm lake with autumn foliage, a dock, and houses along the shore.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Winchester vacation rentals

Interior

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.4 out of 10, Exceptional, (15 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
$185 nightly
The price is $201
Aug 9 - Aug 10
Total with taxes and fees
Winchester's Premier Downtown Loft!
Coffee/tea maker, fridge, microwave, oven

2. 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
$179 nightly
The price is $194
Aug 9 - Aug 10
Total with taxes and fees
Oasis on the Square
Microwave, oven, stovetop, dishwasher

3. 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.
$176 nightly
The price is $176
Aug 11 - Aug 12
Total with taxes and fees
Tiny Home w/ RV Hookups
Interior

4. 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, (7 reviews)
"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "
United States
Gwen K.
$682 nightly
The price is $712
Aug 7 - Aug 8
Total with taxes and fees
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Smart TV, fireplace, stereo

5. Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC

Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
Winchester
7.0 out of 10, Good, (6 reviews)
"This property was perfect for our family and is very close to the marina. Would definitely stay again! "
United States
Emily C.
$162 nightly
The price is $162
Aug 18 - Aug 19
Total with taxes and fees
Cozy 2 BR RV near Tims Ford Lake in Winchester with WiFi, AC
Outdoor dining

6. Stationary tiny camper in Winchester, TN with pond and mountain views.

Stationary tiny camper in Winchester, TN with pond and mountain views.
Winchester
10.0 out of 10, Exceptional, (1 review)
"I definitely give this property 5 gold stars in all categories. It was EXACTLY as advertised with the owner taking care to provide little 'extras' on top of that in the form of snacks, coffee, etc... The electric awning is not even mentioned, but it makes a nice outside sitting area with the provided picnic table. The tiny camper is perfect for a night or a few for 1-2 people. Very clean, great communication and all the things you would want."
United States
Jr H.
$141 nightly
The price is $148
Aug 31 - Sep 1
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
Outdoor dining

7. "The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.2 out of 10, Wonderful, (24 reviews)
"Great little, hidden get-away!"
United States
Rich F.
$458 nightly
The price is $458
Aug 20 - Aug 21
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
Smart TV, table tennis

8. 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, (25 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.
$706 nightly
The price is $706
Aug 12 - Aug 13
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Terrace/patio

9. 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.
$953 nightly
The price is $1,048
Aug 20 - Aug 21
Total with taxes and fees
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Outdoor dining

10. 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
10.0 out of 10, Exceptional, (81 reviews)
"We had a great time! "
United States
Cindy O.
$960 nightly
The price is $960
Aug 9 - Aug 10
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

11. Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (20 reviews)
"This is a fabulous lake house! The view and amenities are perfect! "
United States
Andrea M.
$1,028 nightly
The price is $1,028
Aug 9 - Aug 10
Total with taxes and fees
Lakefront Lodge on Tims Ford Lake
House, 5 Bedrooms | Marina

12. Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
3.0 star property
Winchester
$1,133 nightly
The price is $1,295
Aug 31 - Sep 1
Total with taxes and fees
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Property grounds

13. 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, (37 reviews)
"Very nice! "
United States
Adam H.
$725 nightly
The price is $725
Aug 9 - Aug 10
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Outdoor dining

14. A very rustic converted pole barn unique cozy cabin

A very rustic converted pole barn unique cozy cabin
Estill Springs
9.8 out of 10, Exceptional, (162 reviews)
"Our stay was comfortable and clean."
United States
George A.
$145 nightly
The price is $145
Aug 17 - Aug 18
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin
Interior

15. Queen ensuite room in historic railroad inn & town. Continental breakfast.

Queen ensuite room in historic railroad inn & town. Continental breakfast.
Cowan
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful spot!"
United States
Bennett R.
$145 nightly
The price is $145
Aug 9 - Aug 10
Total with taxes and fees
Queen ensuite room in historic railroad inn & town. Continental breakfast.
Smart TV, fireplace, DVD player

16. Deciduous Dreams in Deer Lick Falls

Deciduous Dreams in Deer Lick Falls
Monteagle
9.0 out of 10, Wonderful, (14 reviews)
"Loved our stay here - such a cozy little tiny home community, private but not isolated. We loved the hike to the waterfall on the property grounds, as well as the gorgeous Fiery Gizzard North trailhead with several other waterfalls just a short drive away. "
United States
Claire H.
$182 nightly
The price is $205
Aug 9 - Aug 10
Total with taxes and fees
Deciduous Dreams in Deer Lick Falls
WiFi (free), bed sheets

17. Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
9.4 out of 10, Exceptional, (8 reviews)
"Omgoodness this place is absolutely amazing!!! We went for a spiritual journey and it was perfect!! The lake & water fall creek with seats sitting in the water was perfect for my reading and meditating. It is absolutely beautiful!!! They had a concert Saturday night, we didn't go to the actual concert but was right beside it and they were fabulous!! Great place to stay! We will definitely return. Thank you so much for everything!"
United States
Tina
$86 nightly
The price is $98
Aug 30 - Aug 31
Total with taxes and fees
Sasquatch Farm
Smart TV

18. The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.6 out of 10, Exceptional, (27 reviews)
"Beautifully decorated, clean cabin. Very comfortable on a beautiful piece of land. Very relaxing and only 15 minute drive to the Caverns!"
United States
Kalindi M.
$161 nightly
The price is $181
Aug 7 - Aug 8
Total with taxes and fees
The Cabin in Tracy City
Lobby

19. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
$182 nightly
The price is $205
Aug 8 - Aug 9
Total with taxes and fees
Whiskey Trails Cottage
Interior

20. Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns

Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Pelham
10.0 out of 10, Exceptional, (6 reviews)
$171 nightly
The price is $193
Aug 25 - Aug 26
Total with taxes and fees
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
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

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

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

10/10 Excellent
"This place is gorgeous. Yes there are a lot of steps, but it’s totally worth it. We could’ve rented a boat or jet, skis, and use the dock - but we ended up just jumping off the dock and swimming. They have a ladder and stairs to get back on the dock and the water is very swimmable - very clean. It’s tucked back into a quiet cove and perfect for a lake getaway.If you like deer, you’ll love this place. There are tons of deer running around everywhere.We actually made a drone footage video of it. We loved it so much. You can see that in the photos."
Garth N. 3-night trip
Posted 2 days ago
Private dock/gazebo on quiet cove. Tims Ford Lake!

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 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?

Private dock/gazebo on quiet cove. Tims Ford Lake!: 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 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Winchester are Lakefront w/Private Dock and Walk to Historic Downtown Winchester! and Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation.

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 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.