Top Villas in Winchester in 2026

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Recommended hotels in Winchester

A gazebo with a caution sign, a brick wall, and a house in the background.

1. Best Western Inn

Winchester

kenneth

Rp2.087.315 total

includes taxes & fees

15 Nov - 16 Nov

A building with a sign for FILO'S TAVERN and another sign for OLDH's BLACK ADVENTURE.

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

Winchester

Rp16.592.862 total

includes taxes & fees

16 Nov - 17 Nov

A two-story motel with a green awning labeled "Quality Inn," featuring a central entrance with a bench and potted plants.

3. Quality Inn Decherd - Winchester

Decherd

Valerie

Rp1.590.765 total

includes taxes & fees

13 Dec - 14 Dec

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

4. Holiday Inn Express Hotel & Suites Tullahoma by IHG

Tullahoma

Kim

Rp1.872.613 total

includes taxes & fees

11 Dec - 12 Dec

A Quality Inn with a covered entrance, stone pillars, and a clear sky.

5. Quality Inn Monteagle

Downtown Monteagle

Gloria

Rp1.499.542 total

includes taxes & fees

13 Dec - 14 Dec

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Learn more about Winchester

Nestled between rolling hills, this charming town offers visitors the crystal-clear waters of Tims Ford Lake for boating and fishing. Explore downtown's historic courthouse square where local shops serve up Southern hospitality alongside the famous Winchester Swamp Festival each September.

See all hotels in Winchester

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

Top reviews in Winchester

Best Western Inn

Winchester

10/10 Excellent

J

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

The Sewanee Inn

Sewanee

10/10 Excellent

Malcolm

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

LivSmart Studios by Hilton Tullahoma

Tullahoma

10/10 Excellent

Daniel

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

Ryan

Holiday Inn Express Hotel & Suites Tullahoma by IHG

Tullahoma

10/10 Excellent

David

A multi-story hotel with a parking lot, marked handicapped parking spaces, and a building illuminated with purple lights.

Microtel Inn & Suites by Wyndham Manchester

Manchester

8/10 Good

Rachel

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

Tolley House

Lynchburg

10/10 Excellent

This was by far the most comfortable bed we slept in! The whole property was wonderful! In the evening we sat on the rocking chair with bottle of Jack and watched fireflies! Very quiet and relaxing! The only confusing bit was the breakfast, the booking it says it was included but there was no breakfast... unless it was make your own as there was some food in the fridge. No staff present at the property or an information page left In the room. We did find some baked goods on arrival in our...

MONIKA

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

The Smokehouse Lodge and Cabins

Monteagle

10/10 Excellent

Charlie

A hotel with a prominent sign for Sleep Inn & Suites, featuring a two-story building with a flat roof and a covered entrance.

Sleep Inn & Suites Manchester near Arnold AFB

Manchester

10/10 Excellent

Very warm and friendly welcome, property being renovated so hard to be critical of some mess but overall disruption was minimal and did not cause us any issues and property will benefit and I am sure will look very nice when finished. Breakfast choice was reasonable and overall good value for money, beds very comfy with nice linen. NOTE if you show room card at Logans or Jeffersons the adjacent restaurants you will get a discount😁👍

Ian

A two-story house with a gabled roof, surrounded by a well-maintained garden with lavender plants.

Mulberry Lavender Farm and B&B

Mulberry

10/10 Excellent

Phil

Room 1

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Recommended hotels in Winchester

1. Best Western Inn

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

3. Quality Inn Decherd - Winchester

4. Holiday Inn Express Hotel & Suites Tullahoma by IHG

5. Quality Inn Monteagle

Learn more about Winchester

Top reviews in Winchester

Best Western Inn

10/10 Excellent

The Sewanee Inn

10/10 Excellent

LivSmart Studios by Hilton Tullahoma

10/10 Excellent

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

10/10 Excellent

Holiday Inn Express Hotel & Suites Tullahoma by IHG

10/10 Excellent

Microtel Inn & Suites by Wyndham Manchester

8/10 Good

Tolley House

10/10 Excellent

The Smokehouse Lodge and Cabins

10/10 Excellent

Sleep Inn & Suites Manchester near Arnold AFB

10/10 Excellent

Mulberry Lavender Farm and B&B

10/10 Excellent

Lynchburg Country Inn

10/10 Excellent

Search Villas in Winchester

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Recommended hotels in Winchester

1. Best Western Inn

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

3. Quality Inn Decherd - Winchester

4. Holiday Inn Express Hotel & Suites Tullahoma by IHG

5. Quality Inn Monteagle

Learn more about Winchester

Top reviews in Winchester

Best Western Inn

10/10 Excellent