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Winchester Vacation Rentals

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    Don't let other travellers get your favourite Winchester area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 12 Rentals in Winchester
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    The following rentals are within 40 kilometres of Winchester.
    Cedar Cabin Lynchburg, TN1 / 18
    (47)Excellent
    Lynchburg
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lynchburg Barrel Cottage1 / 8
    (4)Excellent
    Lynchburg
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Lynchburg
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Monteagle Treehouse Hideawa-Eagle1 / 17
    (8)Excellent
    Monteagle
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • Grill
    • Air Conditioning
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    My newly wed husband and I came to stay here for our honeymoon. Right off the bat when we arrived, I knew we were going to love it. The Eagle cabin, where we stayed was very...
    Reviewed March 27, 2018
    Will definitely return. The owners are great people who genuinely care. The pics do no justice. The loft was great and the kids loved it. The hot tub was amazing. The...
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    About this property
    Unique Retro Style Treehouse! Mountain Top and Wooded location offers travelers room and privacy to breath and relax. We are located only three miles from town, so close to every thing , but, away from the noise of the city. Escape to the Numerous walking trails and waterfalls that the mountain...
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    Monteagle, Tennessee 37356
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    A 3 bedroom home with an amazing and serene view1 / 12
    (1)Excellent
    Monteagle
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 21, 2017
    We enjoyed our stay. The house is very clean with a very good view from the back. We hiked at South Cumberland State Park and Sewanne University. Both are close to the house...
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    About this property
    A private three bedroom/two bath home nestled in an open, yet shaded, one-acre yard with a unobstructed view of the Pelham Valley from the back deck. Rest, relax and enjoy the serenity of this quiet and peaceful retreat. There are a few dates that do not rent for the published pricing,...
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    Monteagle, Tennessee 37356
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tracy City
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Private Garden
    • Air Conditioning
    • Washer
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A unigue get away set in Tennessee's beautiful hills. 20 acres of a reclaimed girls and boys camp, the owners have updated and restored many of the original buildings. The main cabin was the Colonels home, (who began rhe camp in 1946) which is now available for overnight stays. Coming in the near...
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    Tracy City, Tennessee 37387
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lynchburg
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Belle Fleur Cottage - Experience Real Southern Living. Make yourself some Sweet Tea or maybe a Mint Julep in the gourmet kitchen and sit on the screened back porch and watch the Fireflies and wildlife or sit and rock on the front porch. Have your meals at the kitchen table or set a real southern...
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    Location Information
    Lynchburg, Tennessee 37352
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chanticleer1 / 11
    (4)Excellent
    Lynchburg
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Parking
    • Private Garden
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 2017
    A beautiful place in a beautiful setting. The owners are so sweet and always available and eager to make sure your visit is a wonderful one. Definitely worth the price and the...
    Reviewed July 5, 2017
    Great place to stay and in town so many places to shop and plenty to do in surrounding area. People very friendly
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    About this property
    Chanticleer the name of our 1480 sq ft. trailer (mobile home). Located in the gently rolling hills of Lynchburg, Chanticleer site as the first dwelling on a populated dead end road that is a meet 7/10 mile long. It is clean , neat and spacious. Our neighbors are nice and kind. You are in a safe,...
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    Location Information
    Lynchburg, Tennessee 37352
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mulberry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly remodeled Farmhouse on a working goat farm. The rental does not include access to the Barn or farm land. Visiting Lynchburg? This is the perfect place to unplug and enjoy quiet country living. The property does not any visible neighbors. Includes a large porch with a swing. Located 7 miles...
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    Location Information
    Mulberry, Tennessee 37334
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mulberry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay in our cozy cottage with 1860s decor but 21st century comforts. If the dates you have in mind are taken or your traveling with more than two people, you can also check for availability in the farmhouse B&B. The farm was formerly owned by famous distiller Jack Daniel's older brother and...
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    Location Information
    Mulberry, Tennessee 37359
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Bluff View Cabin with breathtaking view & hot tub!1 / 12
    (1)Excellent
    Monteagle
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 1, 2017
    Great cabin in every respect! It has EVERYTHING you could possibly need for a great mountain stay! Owner Lynn is gracious and will go to all lengths to make your stay...
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    About this property
    With some of the most spectacular views of the Cumberland Mountains, this exceptional one of a kind modern cabin with 3 bedrooms and 2 1/2 baths awaits. This unique home is beautifully decorated to make your stay a comfortable experience. The modern kitchen is completely equipped to meet all your...
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    Location Information
    Monteagle, Tennessee 37356
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Mulberry
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mulberry Lavender Farm and Bed and Breakfast, this beautiful farm was once owned by famous distiller Jack Daniel's brother and Civil War soldier Wiley. It is located between Lynchburg and Fayetteville, TN. Choose a spacious room in the farmhouse, or the more private cozy lavender Cottage with a...
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    Location Information
    Mulberry, Tennessee 37359
    Private Room - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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