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

Winchester Vacation Rentals

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Dates

November 2026

December 2026

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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

Gianmarco

SAR 698 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a blue sofa, a staircase, a kitchen, and a fireplace.

2. Iconic Winchester home near Tims Ford State Park!

Winchester

SAR 1,622 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with dark cabinetry, stainless steel appliances, and a light-colored backsplash.

3. Oasis on the Square

Winchester

possible Amanda H

SAR 611 total

includes taxes & fees

11 Nov - 12 Nov

A kitchen with a coffee machine, a sink, and a window with curtains.

4. NEW Shoreline Escape: Lakefront Retreat w/ Hot Tub

Winchester

Vonda R.

SAR 2,055 total

includes taxes & fees

24 Nov - 25 Nov

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

Winchester

Erica P.

SAR 711 total

includes taxes & fees

16 Nov - 17 Nov

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

Winchester

SAR 3,439 total

includes taxes & fees

11 Nov - 12 Nov

7. The Lakeside Getaway

Winchester

Jim C.

SAR 1,597 total

includes taxes & fees

11 Nov - 12 Nov

A log cabin with a porch, outdoor seating, and a welcome sign.

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

Winchester

Rich F.

SAR 1,196 total

includes taxes & fees

11 Nov - 12 Nov

A white RV with 'Campbound' branding parked by a lake with picnic tables and chairs.

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

Winchester

"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."

Jr H.

SAR 609 total

includes taxes & fees

17 Nov - 18 Nov

10. Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Winchester

Gary W.

SAR 8,404 total

includes taxes & fees

29 Nov - 30 Nov

11. A quiet getaway.

Winchester

SAR 1,395 total

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

12. Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

Winchester

Cindy O.

SAR 3,305 total

includes taxes & fees

11 Nov - 12 Nov

A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

13. Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

Winchester

Timothy W.

SAR 2,809 total

includes taxes & fees

15 Nov - 16 Nov

A compact RV interior with a kitchenette, a seating area with a sofa and chairs, and a dining table.

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

Winchester

Emily C.

SAR 769 total

includes taxes & fees

11 Nov - 12 Nov

A kitchen with a double sink, a microwave, and a window with a view of the outdoors.

15. Cozy camper. Queen bed with bunk beds in tranquil Winchester.

Winchester

SAR 824 total

includes taxes & fees

11 Dec - 12 Dec

A compact living space with a kitchenette, a dining area, and a seating area with a sofa.

16. Cozy 2 bed 2 bath camper in Winchester TN.

Winchester

SAR 909 total

includes taxes & fees

11 Dec - 12 Dec

17. Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24

Sewanee

Ryan B.

SAR 991 total

includes taxes & fees

11 Nov - 12 Nov

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".

18. A very rustic converted pole barn unique cozy cabin

Estill Springs

Jacquelyne S.

SAR 703 total

includes taxes & fees

16 Nov - 17 Nov

A spacious interior with wooden beams, a reception desk, and a sign reading "Welcome to the Family."

19. Whiskey Trails Cottage

Tullahoma

Jennifer T.

SAR 676 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a bed, a ceiling fan, a wall-mounted tree decoration, a nightstand with a lamp, and a painting of a sunflower field.

20. SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square

Lynchburg

Patricia

SAR 479 total

includes taxes & fees

12 Nov - 13 Nov

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Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Best Western Inn

Winchester

10/10 Excellent

Cindy

A modern hotel building with a sign reading "LivSmart Studios by Hilton".

LivSmart Studios by Hilton Tullahoma

Tullahoma

10/10 Excellent

Michael

A hotel with a brick facade, a covered entrance, and a parking lot.

Holiday Inn Express Hotel & Suites Tullahoma by IHG

Tullahoma

10/10 Excellent

Penny

A hotel entrance with a stone facade, large glass doors, and a well-lit outdoor area with plants and seating.

Lx Hotel, SureStay Collection by Best Western, Manchester, near Arnold AFB

Manchester

10/10 Excellent

Very clean and spacious room, comfortable bed, thick towels. Communication from the owners was excellent prior to and during our stay. Called in our breakfast order the night before, and were then served our hot homemade breakfast in the lobby dining area in the morning. Would definitely recommend staying at this property again. Extra thoughtful owners also provided a complimentary happy hour and snack in the evening.

Carole

A spacious room with a stone fireplace, a flat-screen TV mounted above it, and a green upholstered sofa.

Quality Inn Monteagle

Downtown Monteagle

10/10 Excellent

Darci

A stone building with a covered patio area, stone pillars, and outdoor seating.

The Sewanee Inn

Sewanee

10/10 Excellent

I had the pleasure of staying at the Sewanee Inn with 3 friends, as our daughters stayed on campus overnight and attended a class the next morning. We had a beautiful evening sitting on the back patio by the golf course, with heat lamps that resembled torches adding to the ambiance. The next morning, we enjoyed a delicious breakfast in the dining room with a friendly, accomodating staff and delicious food! I LOVE it that the Inn has bicycles for guests to use , as the "Green lookout" as well...

Michelle

A lodge with a large wooden overhang, stone pillars, and a stone entrance.

The Smokehouse Lodge and Cabins

Monteagle

10/10 Excellent

Catelyn

A Holiday Inn Express & Suites hotel with a covered entrance, brick facade, and illuminated signage.

Holiday Inn Express & Suites Manchester by IHG

Manchester

10/10 Excellent

Kelly

A modern reception area with a herringbone-patterned carpet, two reception desks, and a wooden partition with a grid design.

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

Manchester

10/10 Excellent

Steve

A modern hotel lobby with a bar area, seating arrangements, and a large window providing natural light.

Microtel Inn & Suites by Wyndham Manchester

Manchester

10/10 Excellent

Erika

A spacious lobby with a reception desk, a seating area, and a view of the outside through a glass door.

Sleep Inn & Suites Manchester near Arnold AFB

Manchester

10/10 Excellent

Leonard

A two-story house with a front porch, stone steps, and two lion statues.

Tolley House

Lynchburg

10/10 Excellent

Ashley

Quality Inn Tullahoma

Tullahoma

10/10 Excellent

Mary M.

A reception desk with wooden barrels, a computer, a clock, and a television on the wall.

Lynchburg Country Inn

Lynchburg

10/10 Excellent

Donald

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.

Winchester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winchester vacation rentals

1. Winchester's Premier Downtown Loft!

2. Iconic Winchester home near Tims Ford State Park!

3. Oasis on the Square

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

5. Tiny Home w/ RV Hookups

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

7. The Lakeside Getaway

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

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

10. Luxurious Lakefront Home- Marina, Boats, and Kayaks!

11. A quiet getaway.

12. Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

13. Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

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

15. Cozy camper. Queen bed with bunk beds in tranquil Winchester.

16. Cozy 2 bed 2 bath camper in Winchester TN.

17. Cozy Pet Friendly Home Away From Home w/ Fenced in Yard & Full Kitchen near I-24

18. A very rustic converted pole barn unique cozy cabin

19. Whiskey Trails Cottage

20. SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Best Western Inn

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Winchester?

What are some of the best vacation home rentals in Winchester?

How many vacation rentals are there in Winchester?

What can I see and do in Winchester?

What are vacation rentals like in Winchester?

4. NEW Shoreline Escape: Lakefront Retreat w/ Hot Tub