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Compare 58 Cottages in Winchester with updated reviews, rates, and availability.

Property grounds
The Blue Heron - Lake Side Chalet
10.0 out of 10, Exceptional, (43)
"Absolutely a perfect getaway for my husband and I. Very quiet and relaxing with the beautiful views of the lake. The home was so cozy and warm ! The kitchen was stocked perfectly with all cooking essentials plus a super comfy king size bed. Thank you, Gloria for sharing your beautiful home!"
The Blue Heron - Lake Side Chalet
Fridge, microwave, oven, stovetop
Lakefront Home, With Hot Tub and Boat deck! Backyard is On the water!
10.0 out of 10, Exceptional, (24)
"House was very warm and inviting. Very well appointed. Yard was well maintained and had plenty of space. Enjoyed the boat deck for fishing. Neighborhood was a little bit tight towing a 27’ boat"
Lakefront Home, With Hot Tub and Boat deck! Backyard is On the water!
Exterior
Hollerback Hunt & Yacht Club, peaceful, family,pet friendly,private dock 6 Acres
9.8 out of 10, Exceptional, (113)
"The serenity and solitude of this property is amazing. We had beautiful fall weather. It was very relaxing. We truly enjoyed our stay."
Hollerback Hunt & Yacht Club, peaceful, family,pet friendly,private dock 6 Acres
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Terrace/patio
Cottage at Tims Ford Lake next to /Marina/ and Restaurant
10.0 out of 10, Exceptional, (16)
"Kelly was very nice and made sure we had everything we needed upon arrival. She was also very responsive. The property was wonderful! It was very clean! My family felt comfortable and we enjoyed our stay!"
The price is $220
$503 total
includes taxes & fees
May 19 - May 20
Cottage at Tims Ford Lake next to /Marina/ and Restaurant
Fridge, microwave, oven, stovetop
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
10.0 out of 10, Exceptional, (21)
"Lovely location and wonderful host, highly recommend!"
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
Property grounds
Lakeside Cottage Retreat at Tim's Ford Lake
10.0 out of 10, Exceptional, (16)
"Great location and neighborhood, said it slept 14 but definitely does not fit 14 comfortably "
Lakeside Cottage Retreat at Tim's Ford Lake
Fridge, microwave, oven, stovetop
New property located on Tim’s Ford Lake
10.0 out of 10, Exceptional, (9)
"This place was a great VRBO. Thank you for actually having comfy beds! Super clean. Super close to a few outdoor activity locations. We enjoyed it even though we didn’t visit during lake season. Absolutely loved the Beer, Bait and Biscuits store down the road and the people who run it."
The price is $275
$584 total
includes taxes & fees
May 17 - May 18
New property located on Tim’s Ford Lake
Fridge, microwave, stovetop, dishwasher
Lakefront Retreat at Waters Edge w/ Fire Pit!
10.0 out of 10, Exceptional, (1)
"We loved this location, the house and the amenities. Can’t wait to stay again!"
Lakefront Retreat at Waters Edge w/ Fire Pit!
Exterior
Tiny Home w/ RV Hookups
The price is $119
$207 total
includes taxes & fees
May 20 - May 21
Tiny Home w/ RV Hookups
Fridge, microwave, oven, stovetop
Quaint Blue Lake Cottage
9.8 out of 10, Exceptional, (26)
"Our stay was great! We didnt have any trouble with check in. The property was just like the photos. Communication was excellent. The views are beautiful. Just a couple of minutes from Elk River Canoe Rental. We hope we will be able to book this year after year."
Quaint Blue Lake Cottage
Pool
Cozy Cabin with large dock on the Lake, Stunning View!
9.8 out of 10, Exceptional, (8)
"Low key, beautiful scenery."
Cozy Cabin with large dock on the Lake, Stunning View!
Property grounds
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant
10.0 out of 10, Exceptional, (10)
"The cottage was very comfortable and the location is quiet. It was also very clean. There is a fully stocked kitchen with appliances and dishes. There is a coffee maker and a Nescafé. I wish I had knows about the nescafe when I was at the store prior to arriving. It is a 10-15 drive to grocery stores and restaurants, with an exception to the restaurant in the marina that is just a golf cart ride away. The hill down to the marina is pretty steep and narrow. The food was decent and the live...
The price is $200
$392 total
includes taxes & fees
May 19 - May 20
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant
Interior
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."
The price is $64
$186 total
includes taxes & fees
May 29 - May 30
Have the Sweetest Dreams @ the Honey Bear Cottage!
Dining tables
Peaceful Mountaintop Cottage
10.0 out of 10, Exceptional, (5)
"We booked this property last minute for a Caverns event due to the close proximity. Our trip started with one minor hiccup that was out of the owner’s control, but she and her daughter worked to quickly resolve the problem late at night. The house is very spacious and has a lot of character. The decor and furniture is all meticulously curated and well laid out (this is not your typical Ikea/wayfair filled rental!!) The guys loved being able to paddle around pond out back and the girls loved the...
The price is $285
$506 total
includes taxes & fees
May 18 - May 19
Peaceful Mountaintop Cottage
Fridge, microwave, oven, stovetop
Snuggle Up in our Teddy Cottage! *New Listing*
10.0 out of 10, Exceptional, (1)
"Easy to get to The Caverns. Absolutely great managers! Chelsea made everything such a breeze even with a couple minor glitches (no fault glitches) she made sure to see everything was the best! "
The price is $54
$173 total
includes taxes & fees
May 20 - May 21
Snuggle Up in our Teddy Cottage! *New Listing*
Interior
Cozy Cottage w/ Private Yard: Pet Friendly!
10.0 out of 10, Exceptional, (7)
"Great spot for a post Thanksgiving family get together and especially great that we were able to bring our dogs as well!"
Cozy Cottage w/ Private Yard: Pet Friendly!
TV
Smarter than the Average Stay at the Yogi Cottage!
10.0 out of 10, Exceptional, (2)
"Comfortable, clean, and. cozy."
Smarter than the Average Stay at the Yogi Cottage!
Exterior
Swordfish Suite DOG friendly- Pup Shed Retreat
10.0 out of 10, Exceptional, (4)
"Really clean. Loved the location - perfect for hiking Fiery Gizzard area. Loved the outdoor spaces. Close to lake and not too close to neighbors."
Swordfish Suite DOG friendly- Pup Shed Retreat
TV
Lakeside Cottage w/Golf Cart, Hot Tub, & Fire Pit
10.0 out of 10, Exceptional, (1)
"Great home for a vacation getaway. Managers are great!"
Lakeside Cottage w/Golf Cart, Hot Tub, & Fire Pit
Terrace/patio
Charming cottage in wooded location
10.0 out of 10, Exceptional, (23)
"I stayed here with 2 friends for our 20th college reunion. The cabin was perfect."
Charming cottage in wooded location
Don't see what you're looking for?
See all available properties in Winchester
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.

Other property types in Winchester

Pool
Family friendly lake front home with private dock in a cove
9.8 out of 10, Exceptional, (16)
"Plenty of room for our family get together. Way larger than pictures show. Would definitely book again next time!!!"
Family friendly lake front home with private dock in a cove
Property grounds
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10.0 out of 10, Exceptional, (16)
"We stayed here for a staff retreat and comfortably had 10 people stay. It's spacious, beautiful, and clean, and the layout is awesome. There's a grocery store nearby for quick runs and close to pickleball courts and hiking. It's right on the lake with an awesome back yard and deck to make mornings and evenings extra great."
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Interior
Luxurious Waterfront Oasis on Tims Ford Lake!
10.0 out of 10, Exceptional, (37)
"We have stayed at quite a few homes and this was by far one of our favorites. Linda was an amazing host and went above and beyond to make our stay memorable."
Luxurious Waterfront Oasis on Tims Ford Lake!
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.

Winchester Cottages information

Number of reviews
329
Accommodation
58 Cottages
Lowest Price
$54
Highest Price
$285

Frequently asked questions

Why book your cottage in Winchester with Expedia?
Reserving a cottage in Winchester is as simple as entering your travel dates and choosing your ideal place for a getaway in nature. From upmarket retreats to low-cost properties and cottages that have perks like a hot tub, Expedia has something for all tastes and styles. As for the best offers around? We’ve got your back!
How can I find cheap cottages in Winchester?
Expedia can help you easily source cheap cottages in Winchester. To find a superb stay in just a few clicks, simply use the filter tool to refine your search by star rating, budget and amenities.
What is there to do in Winchester near my cottage?
The ideal travel accessory is a well-planned schedule. Tims Ford State Park is a wonderful place to kick-start your exploration of Winchester.

Recent reviews of Winchester hotels
Expedia verified reviews

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

5/5 Excellent
Excellent Trip! - Visited local distilleries
"We had a great time at this house. Loved the log cabin feel, it was very cozy and with great amenities. Great communication from the owner. Visited 3 local distilleries, what a fun trip! Would absolutely come back."
A verified traveler stayed at Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
Posted 10 days ago
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks