Find Romantic Hotels in Winchester, TN from $55

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Our top choices for Winchester romantic hotels

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
$47 nightly
The price is $55
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Smokehouse Lodge and Cabins

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
$94 nightly
The price is $108
Dec 28 - Dec 29
Total with taxes and fees
Hampton Inn Kimball

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.
$140 nightly
The price is $160
Dec 11 - Dec 12
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin

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
$201 nightly
The price is $234
Dec 17 - Dec 18
Total with taxes and fees
The Sewanee Inn

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

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.
$234 nightly
The price is $264
Dec 12 - Dec 13
Total with taxes and fees
Cozy Cottage at The Retreat at Deer Lick Falls

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
$175 nightly
The price is $201
Dec 11 - Dec 12
Total with taxes and fees
Sasquatch Farm

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.
$241 nightly
The price is $282
Dec 11 - Dec 12
Total with taxes and fees
Shore Beats Work at The Retreat at Water's Edge

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.
$241 nightly
The price is $282
Dec 12 - Dec 13
Total with taxes and fees
Petite Retreat at The Retreat at Water's Edge

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.
$241 nightly
The price is $282
Dec 13 - Dec 14
Total with taxes and fees
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.

Find out more about Winchester

Winchester attractions for couples

Winchester, Tennessee, offers a delightful mix of outdoor adventures and cultural experiences that will engage families and alike. Start your exploration at the beautiful Tims Ford State Park, where you can enjoy hiking trails, picnicking spots, and stunning views of the shimmering Tims Ford Lake. For a taste of local history, visit the Old Jail Museum, a fascinating site that allows you to step back in time and learn about the region’s intriguing past through its well-preserved artifacts. If you’re looking for family fun, take the kids to the Winchester City Park, which features playgrounds, walking trails, and a serene lake perfect for a family outing or a peaceful afternoon. Don’t miss the chance to explore the Franklin County Arts Guild, where you can find unique local artwork and maybe even participate in a workshop. For accommodations, consider staying in the charming downtown area, where you’ll find hotels offering comfortable amenities and easy access to shops and restaurants, ensuring you feel pampered after a day of exploration. With a mix of comfort, quality, and convenience, Winchester is sure to provide a memorable getaway for your family.

Find the best romantic hotels in Winchester

For couples seeking a romantic getaway in Winchester, Tennessee, these charming hotels offer serene settings and intimate amenities for a memorable stay.

Best Western Inn

  • Why it's great for a couples retreat: The Best Western Inn is an ideal choice for travelers looking to enjoy a cozy and romantic escape without breaking the bank, an excellent guest review rating of 8.8. With a private hot tub available for relaxation, couples can unwind together after a day of exploring the area, making it a perfect retreat for romance.
  • Other amenities: Guests also benefit from a range of amenities designed for comfort, including a 24-hour fitness center and a seasonal outdoor pool for refreshing dips. Enjoy a complimentary full breakfast each morning to start your day right, and take advantage of the kitchenette facilities in your room for intimate in-room dining. Other features include daily housekeeping, free parking, and convenient contactless check-in to enhance your stay.
  • Nearby attractions: County Plaza Shopping Center - 0.73 miles, Franklin County Farmers Market - 0.79 miles, Tims Ford Lake - 1.28 miles

Top Winchester Hotel Reviews

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.

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