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

Sewanee,Cavern,Waterfalls, Hike:Tiny Basecamp New

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 SAR 394
SAR 776 total
includes taxes & fees
19 Feb - 20 Feb
Sewanee,Cavern,Waterfalls, Hike:Tiny Basecamp New

Summit & Shore House at The Retreat at Deer Lick Falls

9.4 out of 10, Exceptional, (15)
"The home was lovely and perfectly appointed. Beautiful outdoor setting and close to terrific hiking and options in town. Comfortable enough to spend all your time at home!"
The price is SAR 378
SAR 1,020 total
includes taxes & fees
17 Feb - 18 Feb
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 SAR 398
SAR 1,056 total
includes taxes & fees
17 Feb - 18 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 SAR 318
SAR 929 total
includes taxes & fees
17 Feb - 18 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 SAR 338
SAR 785 total
includes taxes & fees
17 Feb - 18 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 SAR 2,250
SAR 4,389 total
includes taxes & fees
17 Feb - 18 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 SAR 330
SAR 823 total
includes taxes & fees
23 Feb - 24 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)
"Beautiful home and accommodations. Check in process very easy and accurate description of the property. Will definitely book this place again. :)"
*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 SAR 318
SAR 929 total
includes taxes & fees
17 Feb - 18 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 SAR 970
SAR 1,797 total
includes taxes & fees
17 Feb - 18 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, (39)
"We stayed in this home with some childhood friends. It was a good house for just hanging out and the communication up to, during and after the stay was great!"
New Home, Dock, Home Theatre, Hot Tub, Fire Pit, Kayaks

Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

2.0 star property
10.0 out of 10, Exceptional, (4)
"We enjoyed the house and particularly the hot tub! It was so cold outside. Plenty of rooms and beds, plenty of room for eating and sleeping. Great weekend "
Paradise Resort-Dock, Pool, Hot Tub, Movie Theatre

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 SAR 378
SAR 1,327 total
includes taxes & fees
17 Feb - 18 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!
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

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

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!
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.