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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 60 Cottages in Winchester with updated reviews, rates, and availability.

The Blue Heron - Lake Side Chalet
Property grounds

The Blue Heron - Lake Side Chalet

10.0 out of 10, Exceptional, (67)
"This place was just what we needed to relax and recharge. Just as described and Gloria was wonderful. She simply thought of everything. We will definitely be back. "
The Blue Heron - Lake Side Chalet
Lakeside Cottage Retreat at Tim's Ford Lake
Property grounds

Lakeside Cottage Retreat at Tim's Ford Lake

9.8 out of 10, Exceptional, (28)
"Lovely home, enjoyed our stay."
Lakeside Cottage Retreat at Tim's Ford Lake
Peaceful Mountaintop Cottage
Dining tables

Peaceful Mountaintop Cottage

10.0 out of 10, Exceptional, (7)
"Spent Thanksgiving week at the home. Had everything we needed to cook our Thanksgiving feast. Beautiful decor. It was pretty cold, but the heat worked great and the bedding was cozy. Our pup was very happy. Would definitely stay again. Trivia night at Hank's was so much fun! again.TriviaWoulhappy..verhappy.happy. "
The price is AED 1,047
AED 1,855 total
includes taxes & fees
12 Mar - 13 Mar
Peaceful Mountaintop Cottage
Visit 100 Aker Woods and Stay at Winnie Cottage!
Dining

Visit 100 Aker Woods and Stay at Winnie Cottage!

10.0 out of 10, Exceptional, (4)
"I thoroughly enjoyed my stay and hope to visit again. The cottage was perfect for my needs. "
The price is AED 189
AED 525 total
includes taxes & fees
17 Mar - 18 Mar
Visit 100 Aker Woods and Stay at Winnie Cottage!
Lakeside Cottage w/Golf Cart, Hot Tub, & Fire Pit
TV, fireplace

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

10.0 out of 10, Exceptional, (7)
"We celebrated my dad’s 70th birthday here. House was clean and exactly as described. It was very kid friendly with plenty of room for 10 people. Host was very responsive as well. We already plan on going back! "
Lakeside Cottage w/Golf Cart, Hot Tub, & Fire Pit
Snuggle Up in our Teddy Cottage! *New Listing*
Fridge, microwave, oven, stovetop

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 AED 189
AED 525 total
includes taxes & fees
1 Apr - 2 Apr
Snuggle Up in our Teddy Cottage! *New Listing*
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
Interior

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

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

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 AED 808
AED 1,835 total
includes taxes & fees
12 Mar - 13 Mar
Cottage at Tims Ford Lake next to /Marina/ and Restaurant
Hollerback Hunt & Yacht Club, peaceful, family,pet friendly,private dock 6 Acres
Exterior

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
4 Bedroom cottage on cattle ranch, river access
Beach

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
New property located on Tim’s Ford Lake
Fridge, microwave, oven, stovetop

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 AED 1,010
AED 2,145 total
includes taxes & fees
12 Mar - 13 Mar
New property located on Tim’s Ford Lake
Tennessee Cabin with Hot Tub and Boating Access
Exterior

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
Bluebird Rest - Lakefront Cottage
Property grounds

Bluebird Rest - Lakefront Cottage

10.0 out of 10, Exceptional, (45)
"We absolutely love this house. The lake view is amazing & the back porch & swing is to die for. It’s literally my favorite place on earth. This was our third year in a row visiting & we hope to continue our annual getaway. The neighborhood is so calm & quiet & the house is clean & cozy. Perfect for a peaceful time away. "
Bluebird Rest - Lakefront Cottage
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled
Terrace/patio

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"Nice and cozy place for the family. "
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled
Story-time Stay at Our Rupert Cottage!
Outdoor dining

Story-time Stay at Our Rupert Cottage!

10.0 out of 10, Exceptional, (2)
"Loved staying here. The staff, the cabin, the atmosphere were perfect for this weary traveler! It was great having the consistentcy of the cabin to stay at while seeking my forevervhome in Nashville! I am so grateful"
Story-time Stay at Our Rupert Cottage!
Cottage by the creek, beautiful Mountain View, perfect getaway!!!
Terrace/patio

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!!!
Have the Sweetest Dreams @ the Honey Bear Cottage!
1 bedroom, internet, bed sheets

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 AED 196
AED 533 total
includes taxes & fees
19 Mar - 20 Mar
Have the Sweetest Dreams @ the Honey Bear Cottage!
Swordfish Suite DOG friendly- Pup Shed Retreat
Exterior

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
Smarter than the Average Stay at the Yogi Cottage!
TV

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 AED 196
AED 533 total
includes taxes & fees
6 Apr - 7 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

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Terrace/patio

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
Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart
Exterior

Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart

9.8 out of 10, Exceptional, (20)
"Beautiful and Quiet home. My family enjoyed the spacious home that had all the amenities that made our stay very enjoyable. Will return again"
Beautiful Lake Home Retreat with Lake and Marina Access and Golf Cart
"The Hawk Nest" cabin on Tims Ford Lake
Outdoor dining

"The Hawk Nest" cabin on Tims Ford Lake

9.2 out of 10, Wonderful, (11)
"Just spent the night there to relax and get away got a little bit of work done and was able to relax"
The price is AED 364
AED 1,076 total
includes taxes & fees
23 Mar - 24 Mar
"The Hawk Nest" cabin 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.

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