Find Romantic Hotels in Winchester, TN

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Check availability on Winchester Romantic Hotels

Our top choices for Winchester romantic hotels

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The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

3.0 star property
Monteagle
8.6 out of 10, Excellent, (1148)
"We always stop here in our way to Kentucky. Nice and quiet and staff is nice"
United States
Kevin
The price is ￥7,328
￥8,408 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Smokehouse Lodge and Cabins
Lobby
Hampton Inn Kimball

Hampton Inn Kimball

2.5 star property
Jasper
9.0 out of 10, Wonderful, (631)
"Nice breakfast., friendly staff, large clean room. "
United States
Kathy
The price is ￥14,804
￥16,987 total
includes taxes & fees
Dec 28 - Dec 29
Hampton Inn Kimball
Property grounds
A very rustic converted pole barn unique cozy cabin

A very rustic converted pole barn unique cozy cabin

Estill Springs
10.0 out of 10, Exceptional, (145)
"Relaxing get away...quiet and peaceful you cant get any better than that for a vacation"
United States
Cheryl W.
The price is ￥14,800
￥24,848 total
includes taxes & fees
Dec 11 - Dec 12
A very rustic converted pole barn unique cozy cabin
Exterior
The Sewanee Inn

The Sewanee Inn

4.0 star property
Sewanee
9.8 out of 10, Exceptional, (391)
"Resort is so beautiful. Staff were awesome."
United States
Tanya
The price is ￥31,390
￥36,490 total
includes taxes & fees
Dec 16 - Dec 17
The Sewanee Inn
Terrace/patio
Calming Cabin — Peaceful, Cozy, & Close to Hikes, Waterfalls, The Caverns

Calming Cabin — Peaceful, Cozy, & Close to Hikes, Waterfalls, The Caverns

Tracy City
10.0 out of 10, Exceptional, (62)
"Everything we needed for a quick weekend visit with family in the area!"
United States
Julie S.
Calming Cabin — Peaceful, Cozy, & Close to Hikes, Waterfalls, The Caverns
Property grounds
Cozy Cottage at The Retreat at Deer Lick Falls

Cozy Cottage at The Retreat at Deer Lick Falls

Monteagle
10.0 out of 10, Exceptional, (17)
"Had an awesome time staying at this location. Perfect for a concert at the Caverns and hiking the the South Cumberland. "
United States
Jason Q.
The price is ￥14,862
￥41,072 total
includes taxes & fees
Dec 14 - Dec 15
Cozy Cottage at The Retreat at Deer Lick Falls
Couples treatment rooms, hot stone massages, deep-tissue massages
Sasquatch Farm

Sasquatch Farm

3.0 star property
South Pittsburg
8.0 out of 10, Very Good, (2)
"loved the place and area, only issue was it did seem like it wasn’t properly cleaned before we arrived and found someone’s socks under the pull out couch. But overall everything else was great! "
United States
Mayumi
The price is ￥27,263
￥31,285 total
includes taxes & fees
Dec 11 - Dec 12
Sasquatch Farm
Property grounds
Shore Beats Work at The Retreat at Water's Edge

Shore Beats Work at The Retreat at Water's Edge

Tracy City
9.8 out of 10, Exceptional, (8)
"The house was very nice! I love the comfy back patio. Very peaceful neighborhood."
United States
Patti L.
The price is ￥15,688
￥44,198 total
includes taxes & fees
Dec 18 - Dec 19
Shore Beats Work at The Retreat at Water's Edge
Exterior
Petite Retreat at The Retreat at Water's Edge

Petite Retreat at The Retreat at Water's Edge

Tracy City
9.6 out of 10, Exceptional, (22)
"Such a cute place, just what I needed. Place was clean and fully stocked. Would definitely stay again."
United States
NICOLE C.
The price is ￥15,688
￥43,730 total
includes taxes & fees
Dec 12 - Dec 13
Petite Retreat at The Retreat at Water's Edge
Terrace/patio
Lakeview Oasis at The Retreat at Water's Edge

Lakeview Oasis at The Retreat at Water's Edge

Tracy City
9.6 out of 10, Exceptional, (14)
"The home and the area were great ! Would love to stay again when we have more than one night ! "
United States
Robin M.
The price is ￥15,792
￥44,020 total
includes taxes & fees
Dec 13 - Dec 14
Lakeview Oasis at The Retreat at Water's Edge
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

10/10 Excellent
"The room was spotless. It was the perfect atmosphere before a day on the trails at Coalmont. ONLY suggestion Id have is put a fluffy comforter on the bed. Thank you! Ps. We loved it."
Tambra 1-night trip
Posted 17 hours ago
The Smokehouse Lodge and Cabins

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Frequently asked questions

Searching for romantic hotels in Winchester?
Are you in need of a romantic getaway? You might consider checking out some of the nearby sights and attractions such as Twin Creeks Marina, Tim's Ford Marina, or Tims Ford State Park. If you'd like to stay close to a particular destination, you can sort by neighborhood or distance to top landmarks, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Winchester?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Winchester: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Winchester is 64 inches.
What is there to do in Winchester?
There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Winchester has to offer. A visit to Twin Creeks Marina, Tim's Ford Marina, or Tims Ford State Park might be just the ticket when you're checking out the sights.
What's the best way to get to Winchester and around town during my romantic getaway?
This information about transportation options in Winchester might help your romantic trip go off without a hitch: The closest major airport is Chattanooga Metropolitan Airport (CHA), located 52.8 mi (85 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.