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Compare 70 Cottages in Winchester with updated reviews, rates, and availability.

The Blue Heron - Lake Side Chalet

10.0 out of 10, Exceptional, (72)
"Such a great cottage! Excellent communication with host who even left water and snacks. Kayaks were available but it was far too windy. The porch is a phenomenal place to relax with a book and there was a selection to choose from! Flyers were available for local restaurants and activities. "
The Blue Heron - Lake Side Chalet

Visit 100 Aker Woods and Stay at Winnie Cottage!

9.8 out of 10, Exceptional, (7)
"Most trails were about 15-25 minutes away. Walking distance to an information center. Not a large variety of restaurants, kitchen in cabin had everything you would need to cook anything. Close to 3 different grocery stores,(Save a lot and general dollar in Tracy(small town) and a piggy wiggle ( on the higher price side)"
The price is SAR 193
SAR 536 total
includes taxes & fees
28 Apr - 29 Apr
Visit 100 Aker Woods and Stay at Winnie Cottage!

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

10.0 out of 10, Exceptional, (28)
"Very nice"
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant

Normandy Home w/ Yard ~ 2 Mi to Lake

3.0 star property
9.0 out of 10, Wonderful, (2)
"Everything was perfect for our group! And the owner was very communicative. "
Normandy Home w/ Yard ~ 2 Mi to Lake

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

10.0 out of 10, Exceptional, (26)
"Stayed here for a fishing tournament. Great property for families. This property is located perfectly for easy access to the lake. We would definitely stay again!"
The price is SAR 825
SAR 1,863 total
includes taxes & fees
28 Apr - 29 Apr
Cottage at Tims Ford Lake next to /Marina/ and Restaurant

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

10.0 out of 10, Exceptional, (23)
"We couldn't have been more happy with this home for our girls getaway trip! The place is spectacular with comfy beds and more than enough room for us all. The manager of this property was the best - responding quickly to every inquiry and being wonderful. A"
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, (30)
"Our group had a great stay at this home. It was incredibly well stocked with kitchen essentials, and toiletries in the bathrooms. It is a short walk down to a dock at the lake and connected to a Mariana. There was plenty of room for several families to spend time together. We would absolutely stay here again!"
Lakeside Cottage Retreat at Tim's Ford Lake

Catch Some ZZZ's at the Grizzly Cottage

10.0 out of 10, Exceptional, (1)
"Our family enjoyed a simple low-key stay after catching a show nearby and appreciated the no-frills experience overall. Pricing was great and would not hesitate to stay here again."
The price is SAR 193
SAR 652 total
includes taxes & fees
29 Apr - 30 Apr
Catch Some ZZZ's at the Grizzly Cottage

Bluebird Rest - Lakefront Cottage

10.0 out of 10, Exceptional, (46)
"We just couldn’t get the fish to bite (as our 6 year old stomping around the dock haha). We only wish we got to cruise on the golf cart, but really no need to leave such a beautiful property! "
Bluebird Rest - Lakefront Cottage

Tennessee Cabin with Hot Tub and Boating Access

10.0 out of 10, Exceptional, (8)
"Wonderful house! We plan on traveling to this area again. "
Tennessee Cabin with Hot Tub and Boating Access

Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice and cozy place for the family. "
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled

New property located on Tim’s Ford Lake

10.0 out of 10, Exceptional, (13)
"This place was amazing in every way!! The house had everything we needed and the owner was so very accommodating!! We highly recommend renting from Carrie and know we won’t look any further than this place the next time we are looking for a lake house."
The price is SAR 1,032
SAR 2,180 total
includes taxes & fees
28 Apr - 29 Apr
New property located on Tim’s Ford Lake

Snuggle Up in our Teddy Cottage! *New Listing*

10.0 out of 10, Exceptional, (4)
"Property was just as described and photographed. Sometimes that can be disappointing.Loved the attention to detail in the decor and including all essentials.It was very quiet and safe.Would recommend this property to others!"
The price is SAR 193
SAR 536 total
includes taxes & fees
29 Apr - 30 Apr
Snuggle Up in our Teddy Cottage! *New Listing*

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

9.6 out of 10, Exceptional, (124)
"We absolutely enjoyed our stay. It was beautiful and peaceful. Would love to stay again in the summer months and really be able to enjoy the lake!"
Hollerback Hunt & Yacht Club, peaceful, family,pet friendly,private dock 6 Acres

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

10.0 out of 10, Exceptional, (43)
"I was celebrating my 20th wedding anniversary and also spent some time with my photography telescopes in the beautiful dark skies! Already trying to figure out when I can come back!Cabin was immaculately clean on arrival. "
Cottage by the creek, beautiful Mountain View, perfect getaway!!!

4 Bedroom cottage on cattle ranch, river access

10.0 out of 10, Exceptional, (2)
"Personel were amazing friendly. Senery was beautiful. Tons of amenities (swimming, fishing, canoes, paddle boat, beeby gun shooting, basketball, frisbee golf, grilling, very clean rental houses, and so much more). We will definitely be going back multiple times."
4 Bedroom cottage on cattle ranch, river access

Quaint Blue Lake Cottage

9.8 out of 10, Exceptional, (29)
"clean, but check in was a probem. "
The price is SAR 367
SAR 893 total
includes taxes & fees
28 Apr - 29 Apr
Quaint Blue Lake Cottage

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

Peaceful Mountaintop Cottage

10.0 out of 10, Exceptional, (8)
"Peaceful and quiet. The family area is great! Beds sleep great and the pond is a nice feature. It’s close to Monteagle and local attractions. We went to a concert at The Caverns which a just 5 miles away. It was like home away from home. Great experience. "
The price is SAR 1,069
SAR 1,884 total
includes taxes & fees
28 Apr - 29 Apr
Peaceful Mountaintop Cottage

Smarter than the Average Stay at the Yogi Cottage!

8.4 out of 10, Very Good, (5)
"We stayed here for a concert at the caverns. Property was very nice, house was clean and cozy. We had a shuttle service pick us up right in front of the house. Perfect location and nice hosts!"
The price is SAR 201
SAR 544 total
includes taxes & fees
29 Apr - 30 Apr
Smarter than the Average Stay at the Yogi Cottage!
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

Million Dollar Views: Lakefront, Dock, Kayaks+More

10.0 out of 10, Exceptional, (44)
"We absolutely loved everything about our stay. It was very clean, private, plenty of amenities and the host were amazing. This place had everything you could imagine. Highly recommended. We will definitely be back. Our entire family had a blast. Thanks again "
Million Dollar Views: Lakefront, Dock, Kayaks+More

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

9.8 out of 10, Exceptional, (16)
"Wonderfully maintained property by the lake. So much privacy and great amenities. We will definitely be back."
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

Dock, Water Views, Kayaks, Fire Pit, Game Room

10.0 out of 10, Exceptional, (15)
"Our family of four loved everything about this home. From the second floor family room with a super comfortable, roomy sofa to the well equipped kitchen. We were here for Easter weekend and were able to easily prepare a holiday meal to enjoy.The master bedroom and bath were great. The mattress was perfect. We don’t usually sleep very well the first night away from home but had no problems sleeping comfortably at all.The two guest bedrooms and baths were wonderful for our kids too. They liked...
Dock, Water Views, Kayaks, Fire Pit, Game Room
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.