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Featured Cabin Rentals in Winchester

Escape to your cozy 2-bedroom cabin near Greater Falls

9.8 out of 10, Exceptional, (128)
"Gorgeous and very private setting on a little lake in rural Tennessee. The cabin itself was clean, except for the loads of dead ladybug bodies all over the floor, kitchen counters, and table. Bed was comfortable, kitchen was very well-equipped, and host responded quickly when contacted about issue with water heater. All in all, we enjoyed our stay. "
Escape to your cozy 2-bedroom cabin near Greater Falls

- NEWLY RENOVATED - cabin in gated, mountain community ~ sleeps 6 ~ wifi

10.0 out of 10, Exceptional, (20)
"Wonderful! Will definitely be back. "
- NEWLY RENOVATED - cabin in gated, mountain community ~ sleeps 6 ~ wifi

Relaxing Getaway Cabin in Winchester, TN

9.4 out of 10, Exceptional, (11)
"Super clean property near the lake. Suggest a revision of the door access instructions - took us a few minutes to figure out how to unlock the door. Also, the unit number was not easy to see after dark. Since one of us is sensitive to scents, we removed some of the air wick stations while we were there. Other than those things, it was a great visit with lots of nice amenities from our hosts."
Relaxing Getaway Cabin in Winchester, TN

Escape to Nature @Trailhead Cabins Monteagle.

10.0 out of 10, Exceptional, (18)
"Booked the cabin only a few days in advance, just to get out of Nashville. We could not have asked for a better place to stay. The cabin was spacious, adorable, and CLEAN! The property had great little trails and connected to the Mountain Goat Trail. All of the info for our trip was clear and helpful, sent well before our check-in time. We can’t wait to come back when it isn’t raining to take advantage of the fire pit and peacefulness! "
The price is NZ$387
includes taxes & fees
1 Dec - 2 Dec
Escape to Nature @Trailhead Cabins Monteagle.

"The Hawk Nest" cabin on Tims Ford Lake

9.0 out of 10, Wonderful, (9)
"We love being out in the trees and spending time with nature. This is the perfect spot to just sit back and relax surrounded by trees. "
The price is NZ$507
includes taxes & fees
2 Dec - 3 Dec
"The Hawk Nest" cabin on Tims Ford Lake

Hemlock Falls LLC Mins. From Chattanooga. 2 miles from Foster Falls State Park

10.0 out of 10, Exceptional, (152)
"The accommodations were great and everything worked out great."
Hemlock Falls LLC Mins. From Chattanooga. 2 miles from Foster Falls State Park

Private Multi Family Retreat on 5 Acres!

10.0 out of 10, Exceptional, (8)
"We had a great stay with lots of room and amenities. All the small details add up to a fantastic weekend in the woods!"
The price is NZ$1,997
includes taxes & fees
2 Dec - 3 Dec
Private Multi Family Retreat on 5 Acres!

Calming Cabin: Peaceful & Relaxing | Private, Park-Like | Close to Area Activities

10.0 out of 10, Exceptional, (53)
"We stayed for a long weekend to visit our daughter at Sewanee. The cabin was very nice, the owners easy to contact and talk to, and overall a great stay. Recommended! "
Calming Cabin: Peaceful & Relaxing | Private, Park-Like | Close to Area Activities

3 miles to Jack Daniels Distillery, 5 miles to Lost Creek Boat ramp

10.0 out of 10, Exceptional, (243)
"Loved the location and the cabin!"
The price is NZ$542
includes taxes & fees
3 Dec - 4 Dec
3 miles to Jack Daniels Distillery, 5 miles to Lost Creek Boat ramp

Cozy Tennessee Cabin w/ Deck, Grill & Fire Pit!

9.8 out of 10, Exceptional, (11)
"We had a great time grilling, sitting, playing games, and relaxing! "
Cozy Tennessee Cabin w/ Deck, Grill & Fire Pit!

The Honeysuckle House - Tiny House, BIG Living!

10.0 out of 10, Exceptional, (5)
"The house was wonderful and had everything we needed! Will be recommending to friends and family."
The price is NZ$629
includes taxes & fees
30 Nov - 1 Dec
The Honeysuckle House - Tiny House, BIG Living!

Sunset Hillside Cabin "C" on Horse Farm w/ Hiking

9.2 out of 10, Wonderful, (12)
"Beautiful farm and cabins! I love that it’s pet friendly and has lots of animals around to visit. Ms. Laurie is a great host that went above and beyond. Highly recommend "
Sunset Hillside Cabin "C" on Horse Farm w/ Hiking

Water's Edge-Water Views, Dock/Slip, Hot Tub, Fire Pit, SUPs

9.8 out of 10, Exceptional, (10)
"We had a fantastic stay! The house was stocked with plenty of towels and necessities for our visit and several amenities for us to enjoy throughout the weekend. This was the perfect place for a family gathering. We will be back!"
Water's Edge-Water Views, Dock/Slip, Hot Tub, Fire Pit, SUPs

Treehouse Getaway w/ Hot Tub & Views!

9.4 out of 10, Exceptional, (3)
"The property and views were amazing! Super quiet, as long as your neighbors are quiet. The new Treehouses are cute, but SMALL. Nice bathroom, but sink is ridiculously small. Overall - the new Treehouses are great for two! "
The price is NZ$432
includes taxes & fees
3 Dec - 4 Dec
Treehouse Getaway w/ Hot Tub & Views!

Modern 2-bedroom A-frame with WiFi, AC and hot tub in fabulous Monteagle

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had the best time at this a frame cabin! The inside was immaculate and we enjoyed the hot tub and fire pit! Super clean and had everything we needed. Would highly recommend!"
The price is NZ$507
includes taxes & fees
8 Dec - 9 Dec
Modern 2-bedroom A-frame with WiFi, AC and hot tub in fabulous Monteagle

Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau

10.0 out of 10, Exceptional, (21)
"We wanted to enjoy the fall beauty and take in a few hiked. Great spot to rest your head. "
The price is NZ$318
includes taxes & fees
2 Dec - 3 Dec
Cozy Tiny House Cabin @ Trailhead Cabins. South Cumberland Plateau

our very rusticbarn converted-unique cozy cabin

10.0 out of 10, Exceptional, (120)
"Nice place to relax"
The price is NZ$254
includes taxes & fees
1 Dec - 2 Dec
our very rusticbarn converted-unique cozy cabin

Elk Riverside Escape

10.0 out of 10, Exceptional, (15)
"I stayed here while doing some antiquing nearby. It was nicely suited to my needs, which was basically just a place to crash at night and have coffee in the morning! The river nearby is really lovely and the sound of the waterfall is so nice. You will also hear some road noise, just FYI. It's a cozy space but fairly utilitarian. The bed is super comfy but if you like a full pillow, pack your own. Would likely stay again -- it's a solid value. "
The price is NZ$316
includes taxes & fees
26 Nov - 27 Nov
Elk Riverside Escape

Dove Treehouse Getaway w/ Hot Tub & Firepit!

10.0 out of 10, Exceptional, (271)
"The Dove more than met our expectations! It was well appointed and cozy. It had everything we needed for a weekend visiting our daughter at Sewanee. "
The price is NZ$506
includes taxes & fees
2 Dec - 3 Dec
Dove Treehouse Getaway w/ Hot Tub & Firepit!

Cheerful Riverfront Retreat

9.8 out of 10, Exceptional, (20)
"It was a quick weekend get away and the property was secluded and quiet. It had everything we needed, properly stocked, and a great location for a fall getaway. The property was clean and the check in and check out process was very simple. We would go back if we are in the area again. Thank You Kaleob !!!"
The price is NZ$379
includes taxes & fees
26 Nov - 27 Nov
Cheerful Riverfront Retreat
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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Other property types in Winchester

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

10.0 out of 10, Exceptional, (23)
"We enjoyed spending special family time. The kitchen is perfect for a multi family gathering. Liked having multiple spaces to eat, play games, a do crafts. Having the kayaks (adult and kid size) was wonderful. Realized we were one kayak short late in the week and could have used all that were stated in the description. The kids loved fishing off the dock! Having kids fishing poles was a huge hit! We had to borrow another little kid life jacket from a friend. We rented a boat for the day and the...
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

Family friendly lake front home with private dock in a cove

10.0 out of 10, Exceptional, (22)
"Nice location, easy instructions in the binder to reference information about the stay. Prior guests left some lovely floats by the dock. Friendly neighbors as well."
Family friendly lake front home with private dock in a cove

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

10.0 out of 10, Exceptional, (45)
"My family recently stayed at this immaculate house with incredible views. The house was beautiful and had every amenity you can imagine. The host left us a stocked fridge with some treats for the trip. Everything was spotless and organized so we could walk in and start relaxing immediately. We will definitely return and stay longer so we can enjoy more of the lake in the future. "
Waterfront Oasis On Tims Ford Lake: Pool/Kayak!
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

What are the best cabins near Winchester?
Holiday in one of our 649 cabins in Winchester and be rewarded with picturesque scenery, outdoor fun and memories you’ll never forget. Newly remodeled log cabin near DeSoto State Park & Historic Downtown Mentone is one place where the rhythms of life seem to slow down. Cabin - 3 Miles To Jack Daniels Distillery is another popular option if you need time out in nature.
Are there cheap cabins in Winchester?
Priced between NZ$254 and NZ$1,997 per night, getting away from it all is affordable and easy. Snap up one of our cheap cabins in Winchester and enjoy an adventure-filled holiday without draining your bank account.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 luxury cabins near Winchester offer the ultimate comforts while staying in the great outdoors. You’ll appreciate the quality touches at Lookout Mtn. Tiny cabin close to Rock City & downtown with private hot tub. A spa tub and a deck help make this getaway a top choice. Alternatively, relax and unwind in luxury at Peggers Cabin | Luxury Rustic Tiny Cabin| Spa, which features a spa tub and a deck.
What are the best river cabins near Winchester?
If you’re seeking a character-filled escape near the water, a Winchester river cabin is a terrific choice. Recharge your batteries at Cosy, Riverfront ENTIRE Cabin and let all your troubles scurry away downstream. Handy amenities here include on-site watersports and a wood stove. Another popular riverside getaway is Cheerful Riverfront Retreat. Guests have use of pet-friendly facilities, a firepit and more.
What are the best cabins with pools near Winchester?
Staying in a cabin home with a pool adds even more fun to your holiday. If you’re searching for one near Winchester, - NEWLY RENOVATED - cabin in gated, mountain community ~ sleeps 6 ~ wifi comes with useful amenities like a swimming pool and a barbecue grill to make your poolside escape even more perfect. Tennessee River Gorge® Island Cabins® Swimming Pool is another great pick and features on-site watersports and a swimming pool.
What are some great Winchester cabins?
From upmarket pads with all the nice touches to basic escapes that won’t put a dent in your budget, Expedia has cabin homes to suit every taste and budget. Spend a few days reconnecting with nature at Cabin - Great For Family Holidays, Weddings. Conveniences here include a swimming pool and a barbecue grill. Another attractive option is Cabin - Chattanooga Outdoor Dining Fireplace Hot. It features nearby museums, a barbecue grill and more.
What are the best weekend cabin homes in Winchester?
If you can’t wait to spend two or so carefree days immersed in nature, Cabin - Great For Family Holidays, Weddings awaits. Kick back here for a weekend and enjoy access to amenities including a swimming pool and a barbecue grill. Another favourite retreat is Cabin - Chattanooga Outdoor Dining Fireplace Hot. Offering windsurfing, a spa tub and plenty of peaceful vibes, you’ll go home feeling like a new person.
What are the best cabin prices in Winchester?
With prices from only NZ$254 a night for a cabin home in Winchester, there’s no need to bother with that impossible-to-pitch tent.
Can I find log cabins in Winchester?
If you’re pining for a more relaxed pace of life, you’ll discover it at one of our log cabins in Winchester. For instance, Secluded Log Cabin With Mountain Views. Hot Tub And ‘seasonal’ Heated Pool. Spend your days here hiking and wake boarding and then come home to enjoy its many comforts. Time also seems to pass slowly at Luxurious Log Cabin With Breathtaking Bluff View And Hot Tub. When you’re ready to roam beyond your cosy hideout, cycling and mountain biking opportunities are nearby.
What are the highest-rated cabins in Winchester?
There are some properties that tick just about every box. Cabin - Great For Family Holidays, Weddings is a great example. With an impressive rating, it comes with amenities like a swimming pool, a barbecue grill and much more. Another top option is Cabin - Chattanooga Outdoor Dining Fireplace Hot. Windsurfing and a spa tub are a few of the conveniences you’ll find here.
What are the top things to see and do in Winchester?
Any great cabin getaway just has to include visiting the local sights. For example, Hammers. It’s one of the most popular things to see and do in Winchester. If you’d like to explore beyond the immediate area, rent some wheels and make your way to Tims Ford Marina.
Why should I book a cabin in Winchester?
For a travel experience that’s big on charm, comfort and affordability, it’s hard to top a cabin. Lose your city blues in the greenery of the wilderness. From action-packed days to restful nights cuddled up with your sweetheart, cabins promise both excitement and relaxation. You’ll find all the best Winchester options on Expedia.