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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Winchester cabin rentals

Outdoor dining

"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.4 out of 10, Exceptional, (21 reviews)
"We loved the cabin and we want to stay again soon. "
United States
crystal F.
The price is AED 1,010
AED 1,934 total
includes taxes & fees
27 May - 28 May
"The Hawk Nest" cabin on Tims Ford Lake
Exterior

Sasquatch Farm

Sasquatch Farm
3.0 star property
South Pittsburg
8.8 out of 10, Excellent, (3 reviews)
"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 AED 311
AED 356 total
includes taxes & fees
27 May - 28 May
Sasquatch Farm
Exterior

Deciduous Dreams in Deer Lick Falls

Deciduous Dreams in Deer Lick Falls
Monteagle
9.2 out of 10, Wonderful, (9 reviews)
"This property was everything and more. Our fur baby loved this trip, there is information about what to do around the area and on the property in a binder inside. This came in handy to locate the trails and amazing waterfall on the grounds. There is a super cute pavilion with outdoor fireplace and fire pit, along with rocking chairs for when the nights start to warm up. Definitely plan on returning. "
United States
Pamela
The price is AED 275
AED 661 total
includes taxes & fees
28 May - 29 May
Deciduous Dreams in Deer Lick Falls
Exterior

Flat Branch Lodge - Tracy City, TN

Flat Branch Lodge - Tracy City, TN
Tracy City
9.6 out of 10, Exceptional, (19 reviews)
"Just a lovely stay enjoyed every moment "
United States
Justin D.
The price is AED 239
AED 680 total
includes taxes & fees
28 May - 29 May
Flat Branch Lodge - Tracy City, TN
Exterior

The Cabin in Tracy City

The Cabin in Tracy City
Tracy City
9.8 out of 10, Exceptional, (21 reviews)
"Well made cabin, very cute and cozy! Would definitely stay again"
United States
Laura
The price is AED 202
AED 588 total
includes taxes & fees
27 May - 28 May
The Cabin in Tracy City
Exterior

The Woods at The Retreat at Deer Lick Falls

The Woods at The Retreat at Deer Lick Falls
Monteagle
9.8 out of 10, Exceptional, (39 reviews)
"Loved the little village and house! "
United States
Stephanie S.
The price is AED 350
AED 1,205 total
includes taxes & fees
16 Jun - 17 Jun
The Woods at The Retreat at Deer Lick Falls
Fridge, microwave, oven, stovetop

With Trailhead to One of TN's Tallest Waterfalls

With Trailhead to One of TN's Tallest Waterfalls
Monteagle
9.4 out of 10, Exceptional, (6 reviews)
"Lovely - so enjoyed our stay! So peaceful. "
United States
Elizabeth
The price is AED 287
AED 680 total
includes taxes & fees
15 Jun - 16 Jun
With Trailhead to One of TN's Tallest Waterfalls
Exterior

Chic 2BR Cabin D by MHM Luxury Properties

Chic 2BR Cabin D by MHM Luxury Properties
Jasper
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful birthday getaway! The home was lovely along with the nice amenities Jasper Highlands offers its homeowners. Looking forward to staying again!"
United States
Anonymous traveler
The price is AED 505
AED 1,379 total
includes taxes & fees
3 Jun - 4 Jun
Chic 2BR Cabin D by MHM Luxury Properties
Exterior detail

Private Off-Grid Cabin on a Bluff

Private Off-Grid Cabin on a Bluff
Sequatchie
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful"
United States
Brian M.
The price is AED 327
AED 597 total
includes taxes & fees
9 Jun - 10 Jun
Private Off-Grid Cabin on a Bluff
Exterior

Adventurer at The Retreat at Water's Edge

Adventurer at The Retreat at Water's Edge
Tracy City
9.6 out of 10, Exceptional, (8 reviews)
"The place was very nice. Couldn't ask for a better place. Just wish you had piles of firewood to us at the fire pits"
United States
Amanda L.
The price is AED 350
AED 1,245 total
includes taxes & fees
27 May - 28 May
Adventurer at The Retreat at Water's Edge
Property grounds

The Little Village at The Retreat at Water's Edge

The Little Village at The Retreat at Water's Edge
Tracy City
9.6 out of 10, Exceptional, (9 reviews)
"Very nice spot. We would definitely stay again.Our Host was great!"
United States
Kim C.
The price is AED 331
AED 1,209 total
includes taxes & fees
31 May - 1 Jun
The Little Village at The Retreat at Water's Edge
Exterior

Tiny Home in Deer Lick Falls Community

Tiny Home in Deer Lick Falls Community
Monteagle
9.6 out of 10, Exceptional, (8 reviews)
"Clean and cozy! Awesome waterfall!"
United States
Heather B.
The price is AED 279
AED 672 total
includes taxes & fees
27 May - 28 May
Tiny Home in Deer Lick Falls Community
Exterior

Moonshine Runners Cabin

Moonshine Runners Cabin
Tracy City
10.0 out of 10, Exceptional, (11 reviews)
"This cabin is SO COZY! And the hosts were so responsive and nice. We’ll definitely be staying again."
United States
Abigail O.
The price is AED 347
AED 685 total
includes taxes & fees
27 May - 28 May
Moonshine Runners Cabin
Exterior

The Mountaineer at The Retreat at Deer Lick Falls II

The Mountaineer at The Retreat at Deer Lick Falls II
Monteagle
10.0 out of 10, Exceptional, (11 reviews)
"This was an awesome property! Super cute, comfy, hot tub, fire pit and good location. Really enjoyed our stay here!"
United States
Steve and Shannon B.
The price is AED 389
AED 1,327 total
includes taxes & fees
27 May - 28 May
The Mountaineer at The Retreat at Deer Lick Falls II
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 reviews)
"The property was well maintained. We had a very relaxing and peaceful stay. Will make plans to stay here again."
United States
Danny D.
The price is AED 350
AED 1,202 total
includes taxes & fees
30 May - 31 May
Cozy Cottage at The Retreat at Deer Lick Falls
Exterior

Mini Manor on the Mountain at The Retreat at Water's Edge

Mini Manor on the Mountain at The Retreat at Water's Edge
Tracy City
10.0 out of 10, Exceptional, (15 reviews)
"Very clean and neat cabin. Loved it and will definitely come back. "
United States
Mike M.
The price is AED 428
AED 1,435 total
includes taxes & fees
27 May - 28 May
Mini Manor on the Mountain at The Retreat at Water's Edge
Exterior

A Restful, Modern Tiny B’nB Nestled into the Cumberland Plateau

A Restful, Modern Tiny B’nB Nestled into the Cumberland Plateau
Tracy City
10.0 out of 10, Exceptional, (5 reviews)
"Lovely, bright and clean home w/ all amenities you need and in the center of many outdoor recreational options. Great mix of indoor, screened, outdoor deck and fire pit areas."
United States
Yale M.
The price is AED 422
AED 1,465 total
includes taxes & fees
27 May - 28 May
A Restful, Modern Tiny B’nB Nestled into the Cumberland Plateau
Exterior detail

Lakeview Oasis at The Retreat at Water's Edge

Lakeview Oasis at The Retreat at Water's Edge
Tracy City
9.4 out of 10, Exceptional, (16 reviews)
"We had the best time closing out 2025 at this property. Everything was so nice and provided a great getaway for my husband and me. The view of the lake is beautiful and so peaceful. The house is cozy and welcoming and just what we were looking for."
United States
Christy A.
The price is AED 370
AED 1,262 total
includes taxes & fees
1 Jun - 2 Jun
Lakeview Oasis at The Retreat at Water's Edge
Exterior

Bungalow by the Falls at The Retreat at Deer Lick Falls

Bungalow by the Falls at The Retreat at Deer Lick Falls
Monteagle
9.6 out of 10, Exceptional, (26 reviews)
"Loved staying at the Bungalows by the Falls! Highly recommend!! Loved the private hiking trails and falls!!"
United States
Tonya G.
The price is AED 389
AED 1,327 total
includes taxes & fees
27 May - 28 May
Bungalow by the Falls at The Retreat at Deer Lick Falls
Property grounds

Shore Beats Work at The Retreat at Water's Edge

Shore Beats Work at The Retreat at Water's Edge
Tracy City
9.6 out of 10, Exceptional, (9 reviews)
"A beautiful , charming area with lovely homes In the community. It makes for a nice vacation or retreat. The insides of the Holmes are cozy and efficient"
United States
Paul W.
The price is AED 456
AED 1,392 total
includes taxes & fees
27 May - 28 May
Shore Beats Work 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

Quality Inn Monteagle

Quality Inn Monteagle

10/10 Excellent
"Very well, rounded, and enjoyable breakfast"
Karen 1-night trip
Posted 1 hour ago
Quality Inn Monteagle