Search the Best Cabins in Winchester

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Compare 48 Cabin Rentals in Winchester with updated reviews, rates, and availability.

Exterior
The Sandstone Chalet
10.0 out of 10, Exceptional, (7)
"We fell in love with this property. It was extremely clean and comfortable. If you are looking at booking this property, don't hesitate! You will not be disappointed. It exceeded our expectations."
The price is $225
$460 total
includes taxes & fees
May 19 - May 20
The Sandstone Chalet
3 bedrooms, desk, travel crib, free WiFi
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
10.0 out of 10, Exceptional, (10)
"We had a great time at this house. Loved the log cabin feel, it was very cozy and with great amenities. Great communication from the owner. Visited 3 local distilleries, what a fun trip! Would absolutely come back."
The price is $169
$543 total
includes taxes & fees
May 19 - May 20
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
Property grounds
Escape to Nature @Trailhead Cabins Monteagle.
10.0 out of 10, Exceptional, (8)
"We arrived and there was an outdated code to get in, but Janet was very responsive and fixed the issue right away. The place was clean and had everything we needed for our trip plus more. We would stay here again!"
The price is $79
$226 total
includes taxes & fees
May 20 - May 21
Escape to Nature @Trailhead Cabins Monteagle.
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Terrace/patio
Calming Cabin: Quiet | Peaceful Log Home | Close to Area Activities
10.0 out of 10, Exceptional, (47)
"Very good communication and very clean and peaceful. Had to adjust my schedule and they were very cooperative and communication was outstanding with changes. Went to a concert at caverns and very conveniently located. Definitely recommend and if in area again i definitely will stay again"
The price is $102
$225 total
includes taxes & fees
Jun 10 - Jun 11
Calming Cabin: Quiet | Peaceful Log Home | Close to Area Activities
Exterior
3 miles to Jack Daniels Distillery, 5 miles to Lost Creek Boat ramp
10.0 out of 10, Exceptional, (220)
"Super cute little cabin that was convient to Jack Daniel’s distillery. Also close to Tom’s Ford Lake. Wish we could have stayed longer and relaxed more. "
The price is $125
$220 total
includes taxes & fees
May 19 - May 20
3 miles to Jack Daniels Distillery, 5 miles to Lost Creek Boat ramp
Property grounds
Home away a starting point for your adventures or just to relax.
10.0 out of 10, Exceptional, (2)
"My husband and I were looking for a quiet place to get away for a night. This cabin was perfect! It was clean and nicely furnished and back in the woods so it was nice and quiet. The owner messaged back quickly when we had questions."
The price is $138
$178 total
includes taxes & fees
May 17 - May 18
Home away a starting point for your adventures or just to relax.
Terrace/patio
Elk Riverside Escape
10.0 out of 10, Exceptional, (13)
"Cabin was beautiful, very quiet. "
The price is $95
$186 total
includes taxes & fees
May 20 - May 21
Elk Riverside Escape
Property grounds
Eagle Treehouse Getaway with Hot Tub, Gas Fireplace, and Outdoor Firepit!
10.0 out of 10, Exceptional, (260)
"Such a cute place. Had a great time"
The price is $150
$271 total
includes taxes & fees
May 20 - May 21
Eagle Treehouse Getaway with Hot Tub, Gas Fireplace, and Outdoor Firepit!
Fridge, microwave, oven, stovetop
- NEWLY RENOVATED - cabin in gated, mountain community ~ sleeps 6 ~ wifi
10.0 out of 10, Exceptional, (13)
"Nice, clean, convenient to W&L and VMI. Apartment is just what we needed for visit. Well stocked kitchen, roomy living spaces to hang out. And walkable to downtown and both campuses in Lexington."
- NEWLY RENOVATED - cabin in gated, mountain community ~ sleeps 6 ~ wifi
Property grounds
Private Multi Family Retreat on 5 Acres!
10.0 out of 10, Exceptional, (1)
"This property is so awesome! Not only is it beautiful and aesthetically pleasing, it was equipped with everything we could possibly need. Rachel and Steph really thought of everything, and were so helpful and communicative. Spent the weekend here with friends, cooked tasty meals, enjoyed the beautiful view of trees from our bedroom, relaxed in the sauna, hot tub and pool. The only complaint I have is that we didn’t book a longer stay. 🙂 Definitely will be rebooking this home in the future."
The price is $380
$887 total
includes taxes & fees
May 19 - May 20
Private Multi Family Retreat on 5 Acres!
Fridge, microwave, stovetop, coffee/tea maker
Cozy Tennessee Cabin w/ Deck, Grill & Fire Pit!
10.0 out of 10, Exceptional, (2)
"Great long weekend get away with my sons. Perfect setup for a family guys weekend. Enjoyed this super comfortable cabin that supplied the perfect mix of privacy and community for my grown sons to spend some quality family time."
Cozy Tennessee Cabin w/ Deck, Grill & Fire Pit!
Pool
Hummingbird Treehouse Getaway w/ Hot Tub & Firepit
10.0 out of 10, Exceptional, (357)
"Very nice facility! Very private but accessible to other tourist locations!"
The price is $185
$316 total
includes taxes & fees
Jun 6 - Jun 7
Hummingbird Treehouse Getaway w/ Hot Tub & Firepit
Interior
Monteagle Cabin, Views! Hot Tub!
10.0 out of 10, Exceptional, (25)
"We rented this little gem while picking our daughter up from college and absolutely loved it! The house is a treat, but the cherry on top is the view from the back porch!"
Monteagle Cabin, Views! Hot Tub!
View from property
The Honeysuckle House - Tiny House, BIG Living!
10.0 out of 10, Exceptional, (1)
"Perfect"
The price is $150
$366 total
includes taxes & fees
May 18 - May 19
The Honeysuckle House - Tiny House, BIG Living!
Exterior
Cozy in the woods, your starting point for adventure or relaxation.
10.0 out of 10, Exceptional, (2)
"Ron repeatedly went out of his way to help us and be kind. Truly a great person and great. host"
The price is $138
$178 total
includes taxes & fees
May 20 - May 21
Cozy in the woods, your starting point for adventure or relaxation.
Outdoor spa tub
Water's Edge-Water Views, Dock/Slip, Hot Tub, Fire Pit, SUPs
10.0 out of 10, Exceptional, (6)
"Thoroughly enjoyed our stay. Terrific, quiet location. Better than average appliances/cookware. Outdoor spaces unbeatable. Very attentive property managers."
Water's Edge-Water Views, Dock/Slip, Hot Tub, Fire Pit, SUPs
Property grounds
Mossy Falls Cabin | Outdoor Hot Tub & Fire Pit!
10.0 out of 10, Exceptional, (4)
"Everything was perfect couldn’t have been better"
Mossy Falls Cabin | Outdoor Hot Tub & Fire Pit!
Exterior
"The Hawk Nest" cabin on Tims Ford Lake
10.0 out of 10, Exceptional, (4)
"It was beautiful and my 2 grandchildren loved the swing set. It was clean and quaint and a beautiful view."
The price is $275
$500 total
includes taxes & fees
May 23 - May 24
"The Hawk Nest" cabin on Tims Ford Lake
Property grounds
Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau
9.8 out of 10, Exceptional, (15)
"Quaint and cozy cabin, perfect for a 2 night stay. We loved the loft and how intimate the area felt. Great location only a few minutes from fiery gizzard and not too far off the interstate. Would definitely return!"
The price is $79
$186 total
includes taxes & fees
May 20 - May 21
Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau
Shower, hair dryer, towels, soap
our very rusticbarn converted-unique cozy cabin
9.8 out of 10, Exceptional, (106)
"The hosts were gracious, and never intrusive. We rented the property for our 10 year anniversary and for the relaxation and quiet that the area offered. Ray and Deb were so kind to let us bring our 3 fur babies 2 that are seniors. The bed was AMAZING..So comfortable. All and all we had a great relaxing time, and I have to say the smell of honeysuckle will linger in my memory for a long time!!"
The price is $94
$158 total
includes taxes & fees
May 20 - May 21
our very rusticbarn converted-unique cozy cabin
Don't see what you're looking for?
See all available properties in Winchester
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.

Other property types in Winchester

Property grounds
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10.0 out of 10, Exceptional, (16)
"We stayed here for a staff retreat and comfortably had 10 people stay. It's spacious, beautiful, and clean, and the layout is awesome. There's a grocery store nearby for quick runs and close to pickleball courts and hiking. It's right on the lake with an awesome back yard and deck to make mornings and evenings extra great."
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Interior
Luxurious Waterfront Oasis on Tims Ford Lake!
10.0 out of 10, Exceptional, (37)
"We have stayed at quite a few homes and this was by far one of our favorites. Linda was an amazing host and went above and beyond to make our stay memorable."
Luxurious Waterfront Oasis on Tims Ford Lake!
Property grounds
Million Dollar Views: Lakefront, Dock, Kayaks+More
10.0 out of 10, Exceptional, (30)
"We had an amazing stay. The property was perfect for our family. Even though the water was cold, the younger bunch enjoyed the kayaks. Thanks for a great time with family."
The price is $249
$684 total
includes taxes & fees
May 22 - May 23
Million Dollar Views: Lakefront, Dock, Kayaks+More
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.

Winchester Cabin Rentals information

Number of reviews
1,349
Accommodation
48 Cabin Rentals
Lowest Price
$79
Highest Price
$380

Frequently asked questions

What are the best cabins near Winchester?
Ranging from cozy and quaint to large and luxurious, there are 477 cabins to take your pick of in and around Winchester. Some popular options include Newly Remodeled Log Cabin Near Desoto State Park And Historic Downtown Mentone and Cabin - Quails Nest With Hot Tub - Another Day In Paradise.
Are there cheap cabins in Winchester?
For an unforgettable escape in the great outdoors, you can’t beat our cheap cabins in Winchester. Wake up to the sounds of birds and wildlife from one of our cozy retreats priced from $79 to $380 per night.These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best luxury cabins near Winchester?
Our Winchester luxury cabins offer the ultimate in comfort while staying in nature. You’ll love the plush touches at Cabin In The Sky · Poolhot Tub Rock Climb Slide Chatt Tn 21 Miles. A spa tub and a swimming pool help make this property a popular choice. Alternatively, put your feet up in luxury at Lookout Mtn. Tiny Cabin Close To Rock City And Downtown With Private Hot Tub, which comes with a spa tub and a deck.
What are the best river cabins near Winchester?
Spend your waking hours relaxing around the water and your nights listening to it streaming past at a river cabin near Winchester. Leading the list is Cabin - Natures Tiny Riverside Hideaway. This riverside option offers pet-friendly facilities and a firepit. Alternatively, make yourself at home at Cabin - Cheerful Riverfront Retreat. Along with its idyllic location, highlights here include pet-friendly facilities and on-site watersports.
What are the best cabins with pools near Winchester?
Hop into your swimsuit and splash about whenever your heart desires when you book one of our cabin rentals with a pool. Renovated Cabin In Gated is a favorite. A firepit and a patio are among the other amenities you can take advantage of here. Or you can catch up on some “me time” at Cabin - Get Intents · Get Intentsindoor Poolhot Tub Chatt Tn 21 Miles. Along with its pool, this cabin offers a barbecue grill and a spa tub.
What are some great Winchester cabins?
From deluxe pads with all the perks to rustic retreats that won’t break your budget, Expedia has cabin rentals to suit every kind of adventurer. Spend a few days relaxing in nature at Cabin - Great For Family Vacations, Weddings. Conveniences here include a fireplace and a swimming pool. Another attractive option is Cabin - Chattanooga Outdoor Dining Fireplace Hot. It comes with nearby museums, a barbecue grill and more.
What are the best weekend cabin rentals in Winchester?
If you’d love to spend two or so relaxing days surrounded by nature, Cabin - Great For Family Vacations, Weddings is the perfect place. Get comfy here for a long weekend and enjoy access to conveniences including a fireplace and a swimming pool. Another favorite choice is Cabin - Chattanooga Outdoor Dining Fireplace Hot. Offering a patio, a barbecue grill and rare peace and quiet, you’ll go home feeling refreshed and energized.
What are the best cabin prices in Winchester?
Whether you’re traveling on a tiny budget or want to splurge on your next getaway, you’ll find what you’re after on Expedia. At the moment, you can score a Winchester cabin from just $79 per night.This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Can I find log cabins in Winchester?
For lots of nature lovers, the perfect outdoor vacation just isn’t complete without bunking down in a log cabin filled with character. Get out and active or just switch off and unwind at Vacation At Deer Creek Cabin - It Has It All 4b. Activities such as zip-lining and swimming are on your doorstep here. Another enticing log cabin getaway is Secluded Log Cabin With Mountain Views. Hot Tub And seasonal Heated Pool. Canoeing and wake boarding will keep you occupied when you’re not chilling in your rustic abode.
What are the highest-rated cabins in Winchester?
Expedia travelers keep coming back to Cabin - Great For Family Vacations, Weddings. This standout features plenty of amenities like a fireplace and a swimming pool. It’s not hard to understand why Cabin - Chattanooga Outdoor Dining Fireplace Hot is also popular with vacationers. Conveniences such as a patio and a barbecue grill will help make your stay more comfortable.
What are the top things to see and do in Winchester?
Any memorable cabin break just has to involve some sightseeing. For instance, Hammers. It’s one of the leading attractions around Winchester. If you’d like to venture beyond the immediate area, grab a rental car and make your way to Tims Ford Marina.
Why should I book a cabin in Winchester?
For a vacation in nature that won’t cost a fortune, nothing tops a cabin. Picture yourself waking up to the sounds of wildlife and drinking coffee on a private deck surrounded by idyllic views. Rent a cabin in Winchester and say goodbye to the hectic routine of modern life. Whether they’re in the mountains, by the beach or someplace else, cabins offer a rustic and relaxing experience for those who need a break.

Recent reviews of Winchester hotels
Expedia verified reviews

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

5/5 Excellent
Excellent Trip! - Visited local distilleries
"We had a great time at this house. Loved the log cabin feel, it was very cozy and with great amenities. Great communication from the owner. Visited 3 local distilleries, what a fun trip! Would absolutely come back."
A verified traveler stayed at Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
Posted 10 days ago
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks