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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 4 - Oct 5
Total with taxes and fees
Winchester's Premier Downtown Loft!
A living room with a blue door, a television, and a large white wall.

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 lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

3. 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, (39 reviews)
"Great property!"
United States
Greg B.
$273 nightly
The price is $313
Oct 31 - Nov 1
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
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.

4. 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.
$172 nightly
The price is $196
Oct 5 - Oct 6
Total with taxes and fees
Tiny Home w/ RV Hookups
A stainless steel outdoor grill with four burners, a chimney, and a control panel, set against a wooden fence and surrounded by trees.

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
$509 nightly
The price is $526
Oct 4 - Oct 5
Total with taxes and fees
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A white RV with 'Campbound' branding parked by a lake with picnic tables and chairs.

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.
$150 nightly
The price is $170
Oct 11 - Oct 12
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
A log cabin with a porch, outdoor seating, and a welcome sign.

7. "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)
"Super nice, peaceful get-away. Love the private dock and all the sitting areas outside. Feels secluded and I like it. Very easy access as well."
United States
Andrew N.
$369 nightly
The price is $422
Oct 11 - Oct 12
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

8. 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, (83 reviews)
"We had a great time! "
United States
Cindy O.
$857 nightly
The price is $979
Nov 1 - Nov 2
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

9. 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)
"This property conbined with the unit nexf door worked perfectly for our group of 18 people to enjoy a great 4th of july week at the lake."
United States
Timothy W.
$685 nightly
The price is $782
Oct 12 - Oct 13
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Living area

10. 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, (27 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.
$201 nightly
The price is $230
Oct 11 - Oct 12
Total with taxes and fees
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
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, (167 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.
$145 nightly
The price is $165
Oct 4 - Oct 5
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

12. Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!

Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Pelham
9.6 out of 10, Exceptional, (39 reviews)
"House is kept in great condition, beautiful location, and perfect stay when attending the caverns (12 minutes away)"
United States
Antonio M.
$232 nightly
The price is $261
Oct 6 - Oct 7
Total with taxes and fees
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
A spacious living room with a brown leather sofa, a dining table, and a kitchen area.

13. Eagle’s Escape to Sunset Bluff - With OHV Trailer Parking Space

Eagle’s Escape to Sunset Bluff - With OHV Trailer Parking Space
Monteagle
9.4 out of 10, Exceptional, (10 reviews)
"Perfect little cottage with all the necessities. Backyard firepit was great!"
United States
Scott
$170 nightly
The price is $191
Oct 4 - Oct 5
Total with taxes and fees
Eagle’s Escape to Sunset Bluff - With OHV Trailer Parking Space
A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

14. 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, (14 reviews)
"Nice place to stay. Close to the caverns where we saw a show. Property is very clean. Really nice stay."
United States
Dawn
$170 nightly
The price is $191
Oct 4 - Oct 5
Total with taxes and fees
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A building with a sign reading 'THE LEMON FAIR' and a yellow door.

15. 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)
"Fit the needs for a golf trip away from home. Very charming community in the woods. Place was clean with no issues. Nice loft if you have kids. Would recommend!"
United States
John S.
$279 nightly
The price is $308
Oct 26 - Oct 27
Total with taxes and fees
The Woods at The Retreat at Deer Lick Falls
Island

16. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great stay "
United States
D K.
$176 nightly
The price is $198
Oct 4 - Oct 5
Total with taxes and fees
Whiskey Trails Cottage
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

17. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (22 reviews)
"Tiny Haven was exactly as it was described and was a perfect spot for my family to relax after long days hiking and swimming. The beds are super comfortable and we had everything we needed to make the stay perfect. We enjoyed all the deer that stopped through to check us out. We would definitely stay here again if in the area. Highly recommend!"
United States
Kathleen
$170 nightly
The price is $191
Oct 4 - Oct 5
Total with taxes and fees
Tiny Haven at the Retreat
A cozy living room with a fireplace, wooden flooring, a sofa, and a sliding glass door leading to an outdoor area.

18. Cove Sweet Cove - 3BR + 2BR Near the Caverns!

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
10.0 out of 10, Exceptional, (12 reviews)
"The cabin was just as advertised. It was clean and perfect location for the concert at the cavern. I would book again."
United States
Joanne G.
$216 nightly
The price is $243
Oct 4 - Oct 5
Total with taxes and fees
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
A cozy bedroom with a large bed, a window with a view of greenery, and wooden ceiling beams.

19. Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
9.0 out of 10, Wonderful, (9 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
$150 nightly
The price is $172
Oct 4 - Oct 5
Total with taxes and fees
Sasquatch Farm
A log cabin with a deck, large windows, and a table with chairs.

20. 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.
$218 nightly
The price is $233
Oct 4 - Oct 5
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
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
"Comfortable bed! Spacious room. Great breakfast choices. Very friendly staff."
Susie 1-night trip
Posted 3 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 $197 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?

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!: Visitors like this Winchester vacation home rental. It 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Some other top choices in Winchester are Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre and Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation.

How many vacation rentals are there in Winchester?

Expedia has 114 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.