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

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
The price is AED 338
AED 684 total
includes taxes & fees
4 Oct - 5 Oct
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
The price is AED 320
AED 664 total
includes taxes & fees
11 Oct - 12 Oct
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.
The price is AED 1,466
AED 3,041 total
includes taxes & fees
6 Oct - 7 Oct
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.
The price is AED 337
AED 722 total
includes taxes & fees
5 Oct - 6 Oct
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
The price is AED 441
AED 1,931 total
includes taxes & fees
4 Oct - 5 Oct
*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.
The price is AED 331
AED 625 total
includes taxes & fees
11 Oct - 12 Oct
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.
The price is AED 731
AED 1,551 total
includes taxes & fees
11 Oct - 12 Oct
"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.
The price is AED 1,653
AED 3,595 total
includes taxes & fees
1 Nov - 2 Nov
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.
The price is AED 1,286
AED 2,874 total
includes taxes & fees
12 Oct - 13 Oct
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.
The price is AED 327
AED 844 total
includes taxes & fees
11 Oct - 12 Oct
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.
The price is AED 367
AED 607 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 257
AED 959 total
includes taxes & fees
4 Oct - 5 Oct
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
The price is AED 239
AED 703 total
includes taxes & fees
4 Oct - 5 Oct
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
The price is AED 239
AED 703 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 311
AED 1,131 total
includes taxes & fees
26 Oct - 27 Oct
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.
The price is AED 267
AED 729 total
includes taxes & fees
4 Oct - 5 Oct
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)
"We loved it."
United States
Todd
The price is AED 239
AED 703 total
includes taxes & fees
4 Oct - 5 Oct
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.
The price is AED 239
AED 893 total
includes taxes & fees
4 Oct - 5 Oct
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
The price is AED 481
AED 552 total
includes taxes & fees
1 Nov - 2 Nov
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.
The price is AED 295
AED 856 total
includes taxes & fees
4 Oct - 5 Oct
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

Quality Inn Monteagle

Quality Inn Monteagle

8/10 Good
"Average hotel, no elevator, friendly staff. Room size was big. Coffee was great. Mold in shower"
MARTA 1-night trip
Posted 8 hours ago
Quality Inn Monteagle

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.