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

Winchester Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester holiday 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, (18 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 HK$767
HK$1,522 total
includes taxes & fees
18 Oct - 19 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 HK$727
HK$1,468 total
includes taxes & fees
18 Oct - 19 Oct
Oasis on the Square
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.

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.
The price is HK$728
HK$1,550 total
includes taxes & fees
19 Oct - 20 Oct
Tiny Home w/ RV Hookups
A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

4. 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 HK$78
HK$2,502 total
includes taxes & fees
31 Oct - 1 Nov
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
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 HK$1,028
HK$4,232 total
includes taxes & fees
25 Oct - 26 Oct
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A marina with boats docked, a dock with a covered area, and a sunset over water.

6. 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
The price is HK$2,485
HK$8,146 total
includes taxes & fees
25 Oct - 26 Oct
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
A white RV with 'Campbound' branding parked by a lake with picnic tables and chairs.

7. 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 HK$785
HK$1,426 total
includes taxes & fees
21 Oct - 22 Oct
Stationary tiny camper in Winchester, TN with pond and mountain views.
A log cabin with a porch, outdoor seating, and a welcome sign.

8. "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 HK$1,562
HK$3,313 total
includes taxes & fees
15 Oct - 16 Oct
"The Hawk Nest" cabin on Tims Ford Lake
Living area

9. A quiet getaway.

A quiet getaway.
Winchester
The price is HK$1,570
HK$3,059 total
includes taxes & fees
26 Oct - 27 Oct
A quiet getaway.
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

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, (83 reviews)
"We had a great time! "
United States
Cindy O.
The price is HK$3,532
HK$7,682 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.

11. 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, (27 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 HK$2,747
HK$6,139 total
includes taxes & fees
18 Oct - 19 Oct
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
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".

12. 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 HK$785
HK$1,297 total
includes taxes & fees
16 Oct - 17 Oct
A very rustic converted pole barn unique cozy cabin
Living area

13. 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 HK$735
HK$1,890 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24
Island

14. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great stay "
United States
D K.
The price is HK$618
HK$1,618 total
includes taxes & fees
21 Oct - 22 Oct
Whiskey Trails Cottage
A spacious living room with a grey sofa, a round wicker chair, and large windows offering a view of trees.

15. Lake Life 4 Bedroom, 3 Bath, Sleeps 12.

Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
Estill Springs
9.8 out of 10, Exceptional, (35 reviews)
"Excellent place to stay for a weekend get away with friends or family "
United States
Zack F.
The price is HK$3,002
HK$6,477 total
includes taxes & fees
15 Oct - 16 Oct
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

16. 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 HK$549
HK$2,050 total
includes taxes & fees
26 Oct - 27 Oct
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
A cozy living room with a sofa, armchair, and ottoman, wooden walls, and large windows with curtains.

17. 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, (33 reviews)
"wonderful place to stay right on Sewanee's campus!"
United States
katherine v.
The price is HK$2,394
HK$4,662 total
includes taxes & fees
18 Oct - 19 Oct
On the University of the South campus, Sewanee, TN.
A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

18. 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, (15 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 HK$510
HK$1,502 total
includes taxes & fees
27 Oct - 28 Oct
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A dining area with a wooden table set for four, two grey armchairs, a brick fireplace, and a large window with curtains.

19. Lydia's Lodge in Pelham

Lydia's Lodge in Pelham
Pelham
9.6 out of 10, Exceptional, (15 reviews)
"It was a great p[lace to stay. Very peaceful"
United States
Levi M.
The price is HK$510
HK$1,909 total
includes taxes & fees
18 Oct - 19 Oct
Lydia's Lodge in Pelham
A cozy bedroom with a large bed, a window with a view of greenery, and wooden ceiling beams.

20. Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
9.0 out of 10, Wonderful, (9 reviews)
"This place is amazing! Thank you to the owners and the staff! Also a huge thanks for an amazing fireworks show and the live music was outstanding!"
United States
Kimberly
The price is HK$1,060
HK$1,216 total
includes taxes & fees
15 Oct - 16 Oct
Sasquatch Farm
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

8/10 Good
"Handy access........................."
Gregory 1-night trip
Posted 1 day ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find a holiday rental in Winchester?

Yes, there are holiday rentals in Winchester close to Twin Creeks Marina, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its theme park and lake views. Make sure you have time to check out the university setting and coffee shops during your trip.

What are some of the best holiday rentals that Winchester has to offer?

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!: This highly rated holiday home rental in Winchester 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 that you can cook with friends or family. You can relax into your holiday 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 holiday rentals are there in Winchester?

Expedia has 114 holiday 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 holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.