Search Vacation Homes in Winchester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 308 Vacation Homes in Winchester with updated reviews, rates, and availability.

Isolated wooded home safe and quiet. Perfect for getting away from it all!

8.6 out of 10, Excellent, (4)
"quite and relaxing"
Isolated wooded home safe and quiet. Perfect for getting away from it all!

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

9.6 out of 10, Exceptional, (115)
"Amazing property to stay in. Walking distance to all campus activities"
Charming 120 Year Old Sewanee Home on Campus- Walk Everywhere!

Bluff House: Renovated Lux | Incredible View | Area Activities & The Caverns Close By

10.0 out of 10, Exceptional, (108)
"My brother and I purchased our mom tickets to a Christmas concert in the Caverns and found this gem when planning the trip. The Caverns were only a quick 15 minute drive so it seemed like a perfect fit. We flew into Knoxville and enjoyed the scenic 2.5 hour drive down to Pelham and were ecstatic once we arrived. The hosts met us at the property to explain everything at check-in and couldn't have been more hospitable. We arrived around 9pm and were blown away that you could see EVERY star in...
The price is AED 488
AED 1,107 total
includes taxes & fees
24 Dec - 25 Dec
Bluff House: Renovated Lux | Incredible View | Area Activities & The Caverns Close By

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

9.6 out of 10, Exceptional, (30)
"We loved this house. It’s so cute, well decorated and stocked. It felt like being a guest in someone’s home. Bed were comfy as well. Loved the location. All around pleasant. "
Trillium Ranch located Central to Campus 2 blocks from All Saints!

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 Loft - Lounge with Grill and Hot Tub!

High Point Getaway - Monteagle

2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent large house "
The price is AED 567
AED 1,433 total
includes taxes & fees
3 Jan - 4 January 2025
High Point Getaway - Monteagle

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

Cozy basecamp minutes from waterfalls, hiking and climbing

10.0 out of 10, Exceptional, (14)
"Rustic clean property. No frills. Met our needs perfectly."
The price is AED 455
AED 747 total
includes taxes & fees
6 Jan - 7 January 2025
Cozy basecamp minutes from waterfalls, hiking and climbing

Beautiful Rustic Cabin On Lincoln Lake Is A Sportsman paradise.

9.8 out of 10, Exceptional, (104)
"Clean and everything had a place and easy to find what I needed - great location - Really good host! Very helpful!"
Beautiful Rustic Cabin On Lincoln Lake Is A Sportsman paradise.

Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!

10.0 out of 10, Exceptional, (46)
"It is so adorable!! So cozy and welcoming!! Its was the perfect little get away for my little family!! Thank you for sharing your tiny home with us!"
The price is AED 364
AED 971 total
includes taxes & fees
23 Dec - 24 Dec
Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!

Piney House at The Retreat at Sunset Bluff

10.0 out of 10, Exceptional, (3)
"Beautifully designed glamping like cabin, surrounded by nature but with all the comforts of luxury—plush bedding, modern amenities, and a cozy fire pit for evenings under the stars. It was the perfect blend of rustic charm and modern elegance, offering both tranquility and comfort. "
The price is AED 448
AED 1,412 total
includes taxes & fees
23 Dec - 24 Dec
Piney House at The Retreat at Sunset Bluff

The Yellow Cottage by Tims Ford Lake

8.8 out of 10, Excellent, (18)
"Very Nice!"
The price is AED 294
AED 945 total
includes taxes & fees
6 Jan - 7 January 2025
The Yellow Cottage by Tims Ford Lake

Luxe Nest at The Retreat at Sunset Bluff

10.0 out of 10, Exceptional, (12)
"The cabin was very clean"
The price is AED 389
AED 1,334 total
includes taxes & fees
23 Dec - 24 Dec
Luxe Nest at The Retreat at Sunset Bluff

The Woods at The Retreat at Deer Lick Falls

9.8 out of 10, Exceptional, (26)
"We stayed there for 2 nights seeing our son play with Pigeons Playing Ping Pong at the Caverns. Awesome home, close to the Caverns. Has everything you need and great area with hiking trails. 5 Stars!!"
The price is AED 311
AED 925 total
includes taxes & fees
23 Dec - 24 Dec
The Woods at The Retreat at Deer Lick Falls

Rooster's Roost of Bells Cove

9.6 out of 10, Exceptional, (17)
"Great place and cozy, country home we stayed at four nights. Quiet setting, views, little charming location. Home was nice, large eat in kitchen, plenty of room for 5 adults. Location near Monteagle"
The price is AED 420
AED 1,170 total
includes taxes & fees
26 Dec - 27 Dec
Rooster's Roost of Bells Cove

Cozy Lake Cottage W/ Hot Tub, Kayaks, SUPs, Pool & Firepit

9.4 out of 10, Exceptional, (9)
"Great communication and very clean. Inside a gated community making for a safe and quiet get away! Will definitely stay again when in town!!"
Cozy Lake Cottage W/ Hot Tub, Kayaks, SUPs, Pool & Firepit

Tims Ford Lake Retreat - The Got-Away

10.0 out of 10, Exceptional, (18)
"Super clean, plenty of room and extremely well appointed. Every thing was thought of. Our favorite was coffee on the deck during the chilly mornings with the fireplace."
Tims Ford Lake Retreat - The Got-Away

Hillside Haven at The Retreat at Water's Edge

10.0 out of 10, Exceptional, (14)
"Hillside Have provided us with perfect place to relax just after our 50th wedding anniversary and celebration. The nicely furnished , well decorated abode in the midst of natural surroundings and incredible landscaping plus abundant amenities was quite enjoyable! A soft breeze while sitting in the swing at sunset was the prefect setting for planning some future trips. We are sure Hillside Haven will be a return spot for us! 10 out of 10 rating as it exceeded or expectations."
The price is AED 448
AED 1,148 total
includes taxes & fees
8 Jan - 9 January 2025
Hillside Haven at The Retreat at Water's Edge

The Great Escape at The Retreat at Sunset Bluff

10.0 out of 10, Exceptional, (5)
"Highly recommend this cabin. Have stayed at several cabins in NC and TN, this one was super clean, in a beautiful and safe neighborhood. Would have loved to stay longer. Driveway is a bit steep for regular cars, our Jeep had no problem though. Amazing patio, perfect for grilling or relaxing."
The price is AED 448
AED 1,412 total
includes taxes & fees
23 Dec - 24 Dec
The Great Escape at The Retreat at Sunset Bluff

Tims Ford Lake Access Detached Home, Lynchburg, TN

10.0 out of 10, Exceptional, (241)
"It is a beautiful place in the woods on Tim's Ford Lake. The host is wonderful. We enjoyed the dock, boats, and fishing, and the grandkids loved the water slide and water toys! It's a great place to enjoy a relaxing weekend! I recommend it for any time of the year! We couldn't ask for more pleasant hosts who really work to make the stay enjoyable!"
Tims Ford Lake Access Detached Home, Lynchburg, TN
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchester

Million Dollar Views: Lakefront, Dock, Kayaks+More

10.0 out of 10, Exceptional, (39)
"We have been traveling for weekend trips with our friends for years and this was the best house yet. Beautiful lake views, clean house, well stocked, and room for everyone. We had the best time! "
The price is AED 1,006
AED 2,806 total
includes taxes & fees
28 Dec - 29 Dec
Million Dollar Views: Lakefront, Dock, Kayaks+More

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
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.