We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes and Apartments Winchester, TN and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $323 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Winchester area holiday rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 30 kilometres of Winchester, Tennessee.

    1 / 17
    5 of 5 stars (2) Excellent
    Monteagle
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 12
    Monteagle
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    1 / 12
    Monteagle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    1 / 44
    5 of 5 stars (4) Excellent
    Sewanee
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Porch
    • DVD Player
    • Satellite TV
    • Washer
    • Parking
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Come visit the mountain this summer. It's cooler on the mountain!!! Hike the mountain, snuggle up with an open outdoor fire under the stars and enjoy the spaciousness of a KING SIZE SLEEP NUMBER BED. Call today, we only have the one sweet cottage to rent! A two bedroom cottage on a private 30... View all property information
    Location Information
    Sewanee, Tennessee 37380
    5 of 5 stars Reviewed 20 July 2016
    We stayed here recently and will be back! The cabin is spacious and well-maintained with very comfortable beds. All the little details are exactly right; the kitchen had...
    5 of 5 stars Reviewed 12 April 2016
    Sewanee parents and visitors will love this cottage. A very spacious cottage. 2 bedrooms one with King other with bunk beds. Great big bathroom with oversized garden tub separate...
    See all reviews
    1 / 23
    Monteagle
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • Internet Access
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    All remaining July weekday rates $225.00 plus taxes and cleaning fee. (2 night minimum) Call today! Our second cabin just down the street, Monteagle Cabin Specials for all remaining July weekdays! $225.00 plus taxes and cleaning fee. (2 night minimum) NO SERVICE OR BOOKING FEES TO RESERVE EITHER... View all property information
    Location Information
    Monteagle, Tennessee 37356
    1 / 18
    5 of 5 stars (37) Excellent
    Lynchburg
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Mountain Views
    • Parking
    • Air Conditioning
    • Washer
    • Outdoor Dining Area
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The Cedar Cabin is nestled in the rolling hills of Jack Daniels' home town of Lynchburg, TN. This newly built cabin is beautiful and unique with all hand crafted furniture. It has two bedrooms with king size beds, and attached full bathrooms. The kitchen is fully furnished and the living room... View all property information
    Location Information
    Lynchburg, Tennessee 37352
    5 of 5 stars Reviewed 6 July 2016
    We stayed at Cedar Cabin for 3 nights with our three little children (4 years old and 10 months old twins). The cabin was wonderful and exceeded our expectations, it was...
    5 of 5 stars Reviewed 29 June 2016
    Great place to stay, close to town. The cabin itself had everything we needed. Very clean and nicely decorated. I will stay here again if I'm ever up that way.
    See all reviews
    1 / 5
    Pelham
    5 Bedrooms, 11 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Secure Parking
    • Washer
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come stay at this gorgeous, newly-built mountain retreat with luxury furnishings and a cozy atmosphere. High atop a hill with breath-taking views, surrounded by beautiful Tennessee wilderness, this secluded 4-bedroom, 9 beds, 4 1/2 bath cabin is perfect for business retreats, family fun, or a... View all property information
    Location Information
    Pelham, Tennessee 37366
    1 / 36
    Lynchburg
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Grill
    • Parking
    • DVD Player
    • Patio
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Experience a once-in-a-lifetime getaway, filled with rejuvenating relaxation and fascinating culture, when you stay at this tremendous Lynchburg vacation rental house. Settled in the heart of historic Jack Daniel’s country, this modernly rustic home provides convenient access to all the area’s... View all property information
    Location Information
    Lynchburg, Tennessee 37352
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing