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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation rentals

A modern living room with a built-in aquarium, a leather sofa, and a patterned rug.

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.6 out of 10, Exceptional, (17 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
$172 nightly
The price is $186
Oct 12 - Oct 13
Total with taxes and fees
Winchester's Premier Downtown Loft!
A modern kitchen with dark cabinetry, stainless steel appliances, and a light-colored backsplash.

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
$167 nightly
The price is $181
Oct 11 - Oct 12
Total with taxes and fees
Oasis on the Square
A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

3. 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.
$678 nightly
The price is $775
Sep 13 - Sep 14
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A log cabin with a porch, outdoor seating, and a welcome sign.

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

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.4 out of 10, Exceptional, (26 reviews)
"Great little, hidden get-away!"
United States
Rich F.
$455 nightly
The price is $520
Sep 12 - Sep 13
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
A spacious kitchen with granite countertops, white cabinetry, and a built-in dishwasher. There are multiple windows providing natural light and a view of the outdoors.

5. 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.
$184 nightly
The price is $210
Sep 14 - Sep 15
Total with taxes and fees
Tiny Home w/ RV Hookups
A living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a small table and chairs.

6. *NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
$596 nightly
The price is $624
Sep 13 - Sep 14
Total with taxes and fees
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

7. 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, (82 reviews)
"We had a great time! "
United States
Cindy O.
$960 nightly
The price is $1,097
Sep 13 - Sep 14
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
A modern kitchen with white cabinets, a black countertop, and a central island with chairs.

8. Cove Sweet Cove! Fire pit, Fishing, Lake Fun!

Cove Sweet Cove! Fire pit, Fishing, Lake Fun!
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Loved our stay, the place was great and super clean. Host was very responsive, would definitely stay here again."
United States
Taylor K.
$931 nightly
The price is $1,063
Sep 14 - Sep 15
Total with taxes and fees
Cove Sweet Cove! Fire pit, Fishing, Lake Fun!
A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

9. 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, (38 reviews)
"Very nice! "
United States
Adam H.
$717 nightly
The price is $820
Sep 13 - Sep 14
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A white RV with 'Campbound' branding parked by a lake with picnic tables and chairs.

10. 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.
$159 nightly
The price is $181
Sep 18 - Sep 19
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
A red mailbox with "McCormick Farmall" on it, a black barbecue grill, a red metal table and chairs, and a sign that says "Come In We're Open".

11. 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, (166 reviews)
"This was a perfect stay for us while we were visiting family! We look forward to staying again when we’re in the area."
United States
Jacquelyne S.
$156 nightly
The price is $178
Oct 4 - Oct 5
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin
A cozy bedroom with a large bed, a window with a view of greenery, and wooden ceiling beams.

12. 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
$147 nightly
The price is $169
Sep 16 - Sep 17
Total with taxes and fees
Sasquatch Farm
A cozy living room with a sofa, armchair, and ottoman, wooden walls, and large windows with curtains.

13. On the University of the South campus, Sewanee, TN.

On the University of the South campus, Sewanee, TN.
Sewanee
9.8 out of 10, Exceptional, (32 reviews)
"wonderful place to stay right on Sewanee's campus!"
United States
katherine v.
$555 nightly
The price is $634
Sep 15 - Sep 16
Total with taxes and fees
On the University of the South campus, Sewanee, TN.
A wooden cabin with a circular window, a Harvia sauna, and a wooden bench.

14. Private Multi Family Retreat on 5 Acres!

Private Multi Family Retreat on 5 Acres!
Sewanee
10.0 out of 10, Exceptional, (14 reviews)
"This was a beautiful and very clean house for several generations to stay during Sewanee graduation. It is in a beautiful wooded location very close to Sewanee. The kitchen is well stocked and there are lots of spots to relax on porches. The property is divided up into several separate suite areas, so everyone had their privacy."
United States
Ann K.
$1,050 nightly
The price is $1,135
Sep 14 - Sep 15
Total with taxes and fees
Private Multi Family Retreat on 5 Acres!
A spacious living room with a large window, a flat-screen TV, and a dining area with a wooden table.

15. Settle Down on the Lake – Your Waterfront Escape in Tracy City

Settle Down on the Lake – Your Waterfront Escape in Tracy City
Tracy City
10.0 out of 10, Exceptional, (13 reviews)
"Quiet and beautiful setting for a girls weekend"
United States
Meaghan D.
$368 nightly
The price is $431
Sep 12 - Sep 13
Total with taxes and fees
Settle Down on the Lake – Your Waterfront Escape in Tracy City
A stone fire pit with two chairs, a wooden swing set, and a cabin in a forest.

16. Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
Monteagle
10.0 out of 10, Exceptional, (58 reviews)
"This was a beautiful stay close to all amenities + wonderful hiking trails!"
Canada
Leah
$291 nightly
The price is $327
Sep 13 - Sep 14
Total with taxes and fees
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
A wooden play structure with a slide and swings in a grassy park area.

17. The Woods at The Retreat at Deer Lick Falls

The Woods at The Retreat at Deer Lick Falls
Monteagle
9.8 out of 10, Exceptional, (41 reviews)
"The home was cute, clean and quiet. Would be great for a family but I also enjoyed my stay alone. Love the tiny home neighborhood surrounded by nature."
United States
Skip E.
$275 nightly
The price is $304
Sep 13 - Sep 14
Total with taxes and fees
The Woods at The Retreat at Deer Lick Falls
A cozy living room with a sofa, armchair, and a television on a wooden stand.

18. Llama No Drama Lodge at The Retreat at Deer Lick Falls

Llama No Drama Lodge at The Retreat at Deer Lick Falls
Monteagle
9.6 out of 10, Exceptional, (25 reviews)
"The property was charming, extremely clean, and cozy. The house had all the amenities you would want or need during a short or extended stay. The outdoor spaces were serene with a beautiful wooded scenery a quiet screened in porch with comfy seating. I would definitely stay in that sweet house again.!"
United States
CHRISTEL
$360 nightly
The price is $398
Sep 21 - Sep 22
Total with taxes and fees
Llama No Drama Lodge at The Retreat at Deer Lick Falls
A rooftop terrace with a fire feature, covered seating areas, and a view of a lake and distant landscape.

19. Large cabin-Game Room,Hot tub,Kid Friendly

Large cabin-Game Room,Hot tub,Kid Friendly
Monteagle
10.0 out of 10, Exceptional, (8 reviews)
"Great place to stay!!"
United States
Laura M.
$667 nightly
The price is $752
Sep 14 - Sep 15
Total with taxes and fees
Large cabin-Game Room,Hot tub,Kid Friendly

20. 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, (25 reviews)
"A great deal and a great location- nice and secluded and close to the caverns where we did a couple shows while visiting. Comfortable spot and wonderful hosts. "
United States
Ryan B.
$200 nightly
The price is $229
Sep 13 - Sep 14
Total with taxes and fees
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
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

Comfort Suites Manchester near Arnold AFB

Comfort Suites Manchester near Arnold AFB

10/10 Excellent
"Great place to stay just of the interstate. Polite staff and clean rooms."
Tara L 1-night trip
Posted 14 hours ago
Comfort Suites Manchester near Arnold AFB

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 $185 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?

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 Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation and Enjoy Your Vacation on Tims Ford Lake.

How many vacation rentals are there in Winchester?

Expedia has 113 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 Lake and Elk River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Tims Ford State Park and Hammers.

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.