Search Cottages in Winchester

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Compare 63 Cottages in Winchester with updated reviews, rates, and availability.

The Blue Heron - Lake Side Chalet

10.0 out of 10, Exceptional, (66)
"This property was perfect! We have stayed in many VRBO properties over the years, and this was one of the best. My husband and I wanted to just get away for a couple of days. He loves to fish and the dock right in front of the house was wonderful. I have never seen a home so well equipped with everything and anything you would need. The snack basket was unbelievable. The living areas were pleasant and even more spacious than the pictures looked. The screened in porch was the best - in the...
The Blue Heron - Lake Side Chalet

Hollerback Hunt & Yacht Club, peaceful, family,pet friendly,private dock 6 Acres

9.8 out of 10, Exceptional, (122)
"Enjoyed the families fall vacation. The cabin have everything you can think of. Great location in a quiet, relaxing place. Caught some small fish. We'll definitely be back again. Owner is so nice and very responsive."
Hollerback Hunt & Yacht Club, peaceful, family,pet friendly,private dock 6 Acres

Hiker's Hangout Monteagle

2.0 star property
The price is SAR 317
SAR 761 total
includes taxes & fees
25 Nov - 26 Nov
Hiker's Hangout Monteagle

Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK

10.0 out of 10, Exceptional, (22)
"Our group enjoyed our time at the lake house. The kids enjoyed fishing and kayaking on the lake. It was quiet and just the right vibe for our fall break. Thanks!"
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK

Lakeside Cottage Retreat at Tim's Ford Lake

9.8 out of 10, Exceptional, (26)
"The home was beautiful. Very clean and comfortable with everything you need! Convieniently located close to both distilleries George Dickel and Jack Daniels."
Lakeside Cottage Retreat at Tim's Ford Lake

Cozy Cottage w/ Private Yard: Pet Friendly!

9.8 out of 10, Exceptional, (9)
"Perfect size rental for our family with fenced in yard for the dog. We had the perfect amount of space and great communication for check in. Brandy gave us some great options for nearby restaurants which were great! Thank you for letting us stay"
Cozy Cottage w/ Private Yard: Pet Friendly!

Lakefront Retreat at Waters Edge w/ Fire Pit!

10.0 out of 10, Exceptional, (4)
"Very nice and clean. I would stay again. "
Lakefront Retreat at Waters Edge w/ Fire Pit!

Swordfish Suite DOG friendly- Pup Shed Retreat

10.0 out of 10, Exceptional, (9)
"The owners were amazing! Also the place was perfectly outfitted. Didn’t need one thing or couldn’t make even one suggestion to improve. The ‘pup shed’ for the dog was awesome! My lab loved it. We will definitely be returning and enjoying this rental and beautiful location "
Swordfish Suite DOG friendly- Pup Shed Retreat

Charming cottage in wooded location

10.0 out of 10, Exceptional, (27)
"This is my 5th or 6th time staying in the cottage. Could not be more perfect for an individual or couple. Everything you need... especially the quiet!!! WIFI works great, all the kitchen supplies you need, a short drive to Sewanee, Monteagle, and great midway spot for day trips to Nashville or Chattanooga. "
Charming cottage in wooded location

Cottage at Tims Ford Lake next to /Marina/ and Restaurant

10.0 out of 10, Exceptional, (25)
"We had a splendid time at the perfect place"
The price is SAR 826
SAR 1,887 total
includes taxes & fees
30 Nov - 1 Dec
Cottage at Tims Ford Lake next to /Marina/ and Restaurant

Quaint Blue Lake Cottage

9.8 out of 10, Exceptional, (28)
"Great place for small family to stay while in/near Fayetteville, TN! Clean home, quiet neighborhood, great internet speed and has lake views! Will definitely try to book here again next time we are in town. "
The price is SAR 368
SAR 909 total
includes taxes & fees
30 Nov - 1 Dec
Quaint Blue Lake Cottage

Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant

10.0 out of 10, Exceptional, (26)
"The house is very modern and well kept . Beautiful neighborhood. We were there for an event in Lynchburg and even drove up to Nashville. We would definitely stay here again . "
The price is SAR 751
SAR 1,471 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant

New property located on Tim’s Ford Lake

10.0 out of 10, Exceptional, (13)
"Visited with a group of girlfriends for a weekend away for some R&R. Really enjoyed the hot tub!"
The price is SAR 1,032
SAR 2,204 total
includes taxes & fees
23 Nov - 24 Nov
New property located on Tim’s Ford Lake

Have the Sweetest Dreams @ the Honey Bear Cottage!

10.0 out of 10, Exceptional, (2)
"We enjoyed our stayed in the Bear Hollow cottage. The space was clean and comfortable. It was close to all the amenities in Monteagle and Sewanee."
Have the Sweetest Dreams @ the Honey Bear Cottage!

Peaceful Mountaintop Cottage

10.0 out of 10, Exceptional, (6)
"This charming house is all personality. It is bigger than the pictures make it seem and filled to the brim with amenities and plenty of space for your group to spread out. The backyard, porch and firepit on the lake with its own canoe seal the deal that this is easily the best house I've ever VRBO'd. The host was attentive and full of great knowledge of things to see and do in the area. Whether you're using it as a home base for a concert at Pelham or a jumping off point to explore the gorgeous...
The price is SAR 1,070
SAR 1,904 total
includes taxes & fees
30 Nov - 1 Dec
Peaceful Mountaintop Cottage

Snuggle Up in our Teddy Cottage! *New Listing*

10.0 out of 10, Exceptional, (3)
"Clean , place has some wear on it but overall clean and no problem with my deposit getting returned . I’ve heard friends have issues with other non Vrbo getting charged for damages they did not do . I will stay with VRBO!!"
The price is SAR 201
SAR 649 total
includes taxes & fees
1 Dec - 2 Dec
Snuggle Up in our Teddy Cottage! *New Listing*

Smarter than the Average Stay at the Yogi Cottage!

8.0 out of 10, Very Good, (3)
"Comfortable, clean, and. cozy."
The price is SAR 221
SAR 673 total
includes taxes & fees
1 Dec - 2 Dec
Smarter than the Average Stay at the Yogi Cottage!

Lakeside Cottage w/Golf Cart, Hot Tub, & Fire Pit

10.0 out of 10, Exceptional, (2)
"We rented this property for my sisters wedding shower, very nice property, everything you need on site. Property management was amazing!"
The price is SAR 409
SAR 1,680 total
includes taxes & fees
25 Nov - 26 Nov
Lakeside Cottage w/Golf Cart, Hot Tub, & Fire Pit

Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

10.0 out of 10, Exceptional, (44)
"Anita & Bob are the best. We felt at home with them & their precious animals. I would go back in a heartbeat. The breakfast was delicious."
The price is SAR 657
SAR 1,076 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

Cottage by the creek, beautiful Mountain View, perfect getaway!!!

10.0 out of 10, Exceptional, (42)
"It was an excellent stay all around!!"
Cottage by the creek, beautiful Mountain View, perfect getaway!!!
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

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

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

10.0 out of 10, Exceptional, (45)
"My family recently stayed at this immaculate house with incredible views. The house was beautiful and had every amenity you can imagine. The host left us a stocked fridge with some treats for the trip. Everything was spotless and organized so we could walk in and start relaxing immediately. We will definitely return and stay longer so we can enjoy more of the lake in the future. "
Waterfront Oasis On Tims Ford Lake: Pool/Kayak!
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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