Winchester Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Winchester Vacation Homes

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

10.0 out of 10, Exceptional, (13)
"Loved the home and creek. "
The price is CA $191
CA $421 total
includes taxes & fees
Aug 11 - Aug 12
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

High Point Getaway - Monteagle

2.0 star property
9.4 out of 10, Exceptional, (6)
"Good house for a large group. Great location with easy access to local attractions including the Caverns at Pelham, TN."
The price is CA $158
CA $449 total
includes taxes & fees
Aug 10 - Aug 11
High Point Getaway - Monteagle

Mountain Memories to provide a cozy retreat on your vacation!

9.4 out of 10, Exceptional, (26)
"Really enjoyed my few days there the place was clean and roomy checking in and communication with property owner was nice and easy would definitely recommend this place. "
The price is CA $111
CA $273 total
includes taxes & fees
Aug 18 - Aug 19
Mountain Memories to provide a cozy retreat on your vacation!

Mountain Point of View Cottage

9.8 out of 10, Exceptional, (21)
"Delightful stay"
The price is CA $109
CA $265 total
includes taxes & fees
Aug 13 - Aug 14
Mountain Point of View Cottage

Shea's Chalet - Cozy home in Monteagle, TN

2.0 star property
9.6 out of 10, Exceptional, (10)
"Good location "
The price is CA $137
CA $381 total
includes taxes & fees
Aug 8 - Aug 9
Shea's Chalet - Cozy home in Monteagle, TN

Beautiful Rustic Cabin On Lincoln Lake Is A Sportsman paradise.

9.8 out of 10, Exceptional, (116)
"We really enjoyed the cabin. It’s perfectly located near Lynchburg and Tim fords lake. The bass were hitting and the catfish we caught were big. Looking forward to going back in the summer. "
Beautiful Rustic Cabin On Lincoln Lake Is A Sportsman paradise.

Private dock/gazebo on quiet cove. Tims Ford Lake!

10.0 out of 10, Exceptional, (36)
"The house was very comfortable and clean and the views were beautiful. Eddie communicated with us often and was available whenever we needed him. "
Private dock/gazebo on quiet cove. Tims Ford Lake!

Lake Side Retreat at The Reserve w/ Golf Cart

10.0 out of 10, Exceptional, (32)
"I booked this property for a lake weekend with my family. The location was great for lake access and the house was super clean and stocked with essentials. Matthew was a great host and helped us work through a booking issue on our part and was communicative as needed. Would stay again!"
Lake Side Retreat at The Reserve w/ Golf Cart

Bluff House — Beyond Belief View | Renovated Luxé | Waterfalls, Hikes & Caverns Near By

10.0 out of 10, Exceptional, (118)
"Ben and Tori are excellent hosts and the place is so peaceful and relaxing. "
The price is CA $258
CA $511 total
includes taxes & fees
Sep 7 - Sep 8
Bluff House — Beyond Belief View | Renovated Luxé | Waterfalls, Hikes & Caverns Near By

Lynchburg cottage across from Jack Daniels Barrel Houses, come smell the mash!!

9.8 out of 10, Exceptional, (21)
"The place was very quaint and had everything we needed. It was very close to downtown Lynchburg and the Jack Daniels Distillery. "
Lynchburg cottage across from Jack Daniels Barrel Houses, come smell the mash!!

Enjoy the lake & mountain retreat at The Water & Woods Tiny Home

10.0 out of 10, Exceptional, (23)
"We really enjoyed our stay! The area is very peaceful and quiet. Our accommodations didn’t feel anything like tiny. The home was tidy and thoughtfully supplied with everything that you would expect and more. Loved the movie choices! Thank you for offering up this wonderful place to stay."
Enjoy the lake & mountain retreat at The Water & Woods Tiny Home

Reflection Bay-Dock, Hot Tub, Kayaks

10.0 out of 10, Exceptional, (9)
"Place was great"
Reflection Bay-Dock, Hot Tub, Kayaks

New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

10.0 out of 10, Exceptional, (46)
"Golf cart is a plus"
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Cozy basecamp minutes from waterfalls, hiking and climbing

9.8 out of 10, Exceptional, (22)
"We stayed at the house in front and it was great. Plenty of room, clean and cool eclectic decor. Would book again!"
The price is CA $153
CA $269 total
includes taxes & fees
Aug 11 - Aug 12
Cozy basecamp minutes from waterfalls, hiking and climbing

Dock, Water Views, Kayaks, Fire Pit, Game Room

10.0 out of 10, Exceptional, (22)
"Great time was had, place was clean and just what we needed."
Dock, Water Views, Kayaks, Fire Pit, Game Room

Clementine Cottage- Quiet Charming Cottage on Lincoln Lake

10.0 out of 10, Exceptional, (94)
"I kind host and a beautiful clean homey place to stay. Bring binoculars great bird watching"
Clementine Cottage- Quiet Charming Cottage on Lincoln Lake

NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub

10.0 out of 10, Exceptional, (72)
"Owners of this property are great, gave us extra days without cost due to bad weather during our stay. We will be back."
The price is CA $618
CA $1,345 total
includes taxes & fees
Sep 1 - Sep 2
NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub

Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall

10.0 out of 10, Exceptional, (10)
"Had a great stay! We’ve stayed in tiny homesbefore & were surprised by how roomy it was. Enjoyed the outdoor area… will definitely be back!"
The price is CA $124
CA $333 total
includes taxes & fees
Aug 10 - Aug 11
Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall

Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!

9.6 out of 10, Exceptional, (131)
"House was conveniently located and very clean. Provided the "
Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!

Beautiful Monteagle Bluff Mountain Home Sleeps 12

10.0 out of 10, Exceptional, (100)
"our party had such a wonderful time here!! breathtaking view especially at sunset. We made wonderful memories here and would love to return!"
Beautiful Monteagle Bluff Mountain Home Sleeps 12
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews