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Compare 318 Vacation Homes in Winchester with updated reviews, rates, and availability.

Sewanee,Cavern,Waterfalls, Hike:New Tiny Basecamp

10.0 out of 10, Exceptional, (26)
"Nestled back in the trees, Tiny Mojo was stunning! Somsamay exceeded our expectations by thinking of everything we could possibly need. We felt cozy & at home & pampered. We can’t wait to return & see Tiny Mojo in the Spring & Fall. Thank you for a beautiful getaway."
The price is AED 411
AED 779 total
includes taxes & fees
27 Feb - 28 Feb
Sewanee,Cavern,Waterfalls, Hike:New Tiny Basecamp

Summit & Shore House at The Retreat at Deer Lick Falls

9.4 out of 10, Exceptional, (15)
"My only complaint is it was very hard to control the A/C temperature and the bathroom shower did not drain well. Communication between with the property manager through VRBO when trying to check in two days early was difficult. The property manager was not receiving my messages through VEBO. It was clean and peaceful."
The price is AED 370
AED 1,003 total
includes taxes & fees
3 Mar - 4 Mar
Summit & Shore House at The Retreat at Deer Lick Falls

Million Dollar Views: Lakefront, Dock, Kayaks+More

10.0 out of 10, Exceptional, (40)
"The house is clean, updated and the views are amazing! We were there in January, so we didn't use the dock, but the house was perfect. The living space and kitchen is large and open, the bedrooms are spacious, and the movie screen set up downstairs was perfect to watch a game and a movie. Will be back!"
Million Dollar Views: Lakefront, Dock, Kayaks+More

Charming 120 Year Old Sewanee Home on Campus- Walk Everywhere!

9.6 out of 10, Exceptional, (115)
"Scott was excellent at communication when a problem occurred. He even let us arrive a night early with no charge to beat the snow. We enjoyed a snowy weekend! The campus was beautiful blanketed in snow and my boys enjoyed burgers on the grill when Clurg and restaurants were closed. Thank you Scott!"
Charming 120 Year Old Sewanee Home on Campus- Walk Everywhere!

The Ascent at The Retreat at Deer Lick Falls II

10.0 out of 10, Exceptional, (2)
"Was only able to stay for one night, but definitely plan to come back for a longer visit. Seems like it would be a great place to hang out outside in nice weather "
The price is AED 389
AED 1,027 total
includes taxes & fees
24 Feb - 25 Feb
The Ascent at The Retreat at Deer Lick Falls II

Spacious Lakefront Retreat w/ Hot Tub + Dock!

10.0 out of 10, Exceptional, (19)
"Our stay was very nice overall. House was clean and host was very communicative. Great views from the kitchen and the porch. My only complaint is that the lake was drawn down when visited (January), so the dock was sitting on dirt. The only critters within casting distance of the dock were squirrels. Probably a lovely place in the Spring and Summer."
Spacious Lakefront Retreat w/ Hot Tub + Dock!

On the Edge at The Retreat at Deer Lick Falls

10.0 out of 10, Exceptional, (12)
"We stayed here attending a concert at The Caverns. Perfect place to stay! Exactly as described! We would love to come back!"
The price is AED 311
AED 899 total
includes taxes & fees
24 Feb - 25 Feb
On the Edge at The Retreat at Deer Lick Falls

Mountain Memories to provide a cozy retreat on your vacation!

10.0 out of 10, Exceptional, (15)
"Clean nice place no problems."
The price is AED 331
AED 769 total
includes taxes & fees
24 Feb - 25 Feb
Mountain Memories to provide a cozy retreat on your vacation!

Whiskey Trails Cottage

10.0 out of 10, Exceptional, (2)
"The property itself is in a quiet neighborhood. It was neat and clean and was the perfect situation for my coworker and I for a week of I service training. Daniel was very communicative and did everything possible to make sure we had a good stay, down to snacks and water in the fridge! We loved staying here and will definitely rebook next time we have training. "
Whiskey Trails Cottage

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

10.0 out of 10, Exceptional, (67)
"Perfect"
The price is AED 2,204
AED 4,298 total
includes taxes & fees
24 Feb - 25 Feb
NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub

The Loft - Lounge with Grill and Hot Tub!

10.0 out of 10, Exceptional, (4)
"The home and property are exactly as the listing states. The hot tub had not been cleaned or we would have rated 5 stars in all the categories. We notified the owner and he had someone there the next day. Overall, we enjoyed our stay!! "
The price is AED 323
AED 813 total
includes taxes & fees
26 Feb - 27 Feb
The Loft - Lounge with Grill and Hot Tub!

*Rare Find* Best Lot with Dock and Views on Lake

2.0 star property
10.0 out of 10, Exceptional, (2)
*Rare Find* Best Lot with Dock and Views on Lake

Riverside Getaway - Enjoy Quiet Life Right on the Duck River

9.2 out of 10, Wonderful, (9)
"Rooms were clean. Beautiful house."
Riverside Getaway - Enjoy Quiet Life Right on the Duck River

Deciduous Dreams at The Retreat at Deer Lick Falls

9.6 out of 10, Exceptional, (11)
"We stayed for the weekend and it happened to snow overnight. This house was great for relaxing but we didn’t get to enjoy the outdoors because of the cold and snow which was unfortunate. We had looked forward to sitting on the porch and by the fire pit as well as walking the trails. The house was warm and cozy with everything you could need. "
The price is AED 311
AED 899 total
includes taxes & fees
26 Feb - 27 Feb
Deciduous Dreams at The Retreat at Deer Lick Falls

Miss Elizabeth's Place | Downtown Lynchburg

10.0 out of 10, Exceptional, (3)
"The owners were very responsive and accommodating and the house was situated perfectly between the distillery and the Mrs Mary Bobos. The house was quite charming and in good shape and the beds were very comfortable. We would definitely stay again and recommend it!"
The price is AED 950
AED 1,771 total
includes taxes & fees
24 Feb - 25 Feb
Miss Elizabeth's Place | Downtown Lynchburg

Trillium Ranch located Central to Campus 2 blocks from All Saints!

9.6 out of 10, Exceptional, (32)
"This is a very comfortable and well appointed house that is close to everything on the Sewanee campus. It sleeps 6 easily and would be great for a group or family visiting campus for a tour or big weekend. While the weather was snowy this trip, the outdoor area would be great in nice weather. We’ll definitely check availability when we are headed to visit again. "
Trillium Ranch located Central to Campus 2 blocks from All Saints!

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

10.0 out of 10, Exceptional, (40)
"The house was great! We had lots of room for everyone and our kids really enjoyed the hot tub and ping pong table. We enjoyed our stay and would definitely stay again in the future! "
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Luxe Nest at The Retreat at Sunset Bluff

10.0 out of 10, Exceptional, (14)
"A very efficient place that comfortably slept 6 of us. The bunk beds are especially useful, though the lack of outlets in each bunk is a big miss.Only underwhelming part was the cleanliness when we arrived. Cleaners missed trash in the loft and fire pit. And we had to rewash many of the dishes in the cabinets because they were either not washed or not washed well."
The price is AED 370
AED 1,285 total
includes taxes & fees
24 Feb - 25 Feb
Luxe Nest at The Retreat at Sunset Bluff

Modern Tims Ford Lake Home w/ Private Dock & Pool!

9.8 out of 10, Exceptional, (9)
"Highly recommended if you are visiting Lynchurg and looking for a place to stay that is close. The only issue we ran into was the code not working when we arrived. The owner picked up immediately when we called and we happy to assist. It turns out we were just a littler early. But he opened it anyway and was extremely friendly. It gave us are real peace of mind knowing someone was reachable that fast. But the house was perfect and no other assistance needed."
Modern Tims Ford Lake Home w/ Private Dock & Pool!

Eagle's Point - Sleeps 12 with an incredible view!

9.8 out of 10, Exceptional, (100)
"very comfortable and clean property. wonderful setting. Host Gary was very accommodating and quick to respond to any inquiries. had a great time. would recommend."
Eagle's Point - Sleeps 12 with an incredible view!
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

"The Hawk Nest" cabin on Tims Ford Lake

9.0 out of 10, Wonderful, (10)
"This is a clean, comfortable and well-appointed cabin and a well-maintained property. It was perfectly simple and had everything we needed…even a flashlight, which we forgot. Our host generously accommodated our special request. Access to water with a kayak was easy. We would love to rent this again! Leslie November 2024"
The price is AED 364
AED 1,072 total
includes taxes & fees
1 Mar - 2 Mar
"The Hawk Nest" cabin on Tims Ford Lake

Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks,

10.0 out of 10, Exceptional, (5)
"A get together for high school friends after many years and we all turned 60. "
Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks,
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.