
Vacation rentals with a kayak in Winchester
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Top-rated kayak rentals in Winchester
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House rentals with a kayak

Barefoot Dreams
I’ve probably stayed at over 100 Airbnb’s over the years and this one is definitely in the top three overall. Fully stocked, spotless, convenient, responsive host, and just a wonderful property. Right across the street from the community pool and the lake. Literally couldn’t ask for a better place for a relaxing weekend with families.

Beautiful cottage next to Tims Ford Lake
Matt was very sweet and gave us many helpful tips during our stay! I would 100% recommend this place to anyone who is trying to have a peaceful and laidback vacation!

Tims Ford *FreeUTV/kayaks/canoe*2.5 acres/private
Noni’s place is such a great place to stay. The area is isolated and the country setting is idyllic. Her home is spacious and so comfortable and clean. The kitchen is stocked, the beds are comfortable, and she’s thought of every amenity you’d need. We’d stay again if we are in the area.

Lakeside Serenity: Cove Retreat
I felt like a welcomed guest from the minute I walked in. The home was spotless and smelled so clean and fresh. I have rented in Tennessee for the last 15 summers and have never rented a place that had so many extras (smores-popcorn- coffee pods-toiletries-kitchen supplies-etc. .Phil checked in to make sure everything was O:K. It is an absolute 5 Star !!!!

Blue Heron Lake House
Spectacular views! The house has everything you'll need either for a romantic getaway or a family gathering. Quick response from the owners regarding booking and normal house maintance issues. The charming home decor gives the house a relaxing vibe and the kitchen has everything you'll need to cook for a big family BBQ or a romantic dinner for two. We had a great experience, would definitely recommend!

Tennessee Pearl: lakefront-amazing views-lake toys
The home was absolutely beautiful, perfectly decorated, and well layed out design. We felt right at home the entire time and absolutely loved all the included amenities! Thank you again for sharing your home with us!

Catch & Release - Spacious Lakefront Getaway
What a wonderful experience! Thank you Elizabeth! This beautiful house on the water was more than I expected. I stayed during a holiday weekend and it was so quiet and peaceful. I kayaked on the lake, hiked the north part of Fiery gizzard, built fires in the fire pit and read lazy beach reads on the screened in porch during afternoon showers. The house was beautiful and clean. It made me question why I would need anything more.(I don’t ) This was a perfect getaway. Thank You again, I can’t wait to come back!

Grand Lakeview: Double decker dock, Fire Pit, Spa
Melissa, Thankyou for letting us enjoy your beautiful home! The rooms were comfortable and beautiful. I appreciated: The beautiful views out the windows. The charging blocks in each room. The great variety of housewares in the kitchen. The view of the dock from the kitchen table (could watch my son-in-law and grandson catch fish). We all spent most of our time there-playing games, eating, etc. Plenty of hot water and good water pressure in the showers. The beds were so cozy and comfortable. Lots of extra super soft blankets to add to beds, if needed. The amenities furnished in the bathrooms were nice plus Plenty of Drawers. 😊 Loved the photo over the master bedroom entrance. And I know you arranged the not too hot weather! It was just perfect! My 88 year old Mom appreciated the Ion and Lifetime channels! 😊It’s the first trip she’s been on w/ us in years-she settled right in in front of the tv in the living room and said she would come back. Great Place/Great Host/Great Times
Cottage rentals with a kayak

Bluebird Rest- Peaceful Lake Retreat
Stellar lake house with incredible views, fantastic design features, and perfect vacation amenities! Sheila was an amazing host with wonderful communication throughout our stay. The home was a perfect escape for coffee-filled morning porch-sitting and cozy evenings inside watching fireflies. Our weekend plans were derailed by weather. We were blessed to have Sheila’s lovely home as a place for new flexible planning around the area. Winchester, Lynchburg, and Fayetteville had charming town squares and a few attractions to explore. Extraordinary home that is a one of a kind place for all sorts of fun! Thank you, Sheila!

Lake it Oar Leave it- Lakefront on Tim's Ford Lake
worked over very well. Spoke with Tara about the upstairs heat unit, breaker was tripping or not functional

Clementine Cottage
The Clementine Cottage was perfect. It was cute, quaint, CLEAN, well outfitted with lots of nice extras. She had brochures on all the nearby activities. We fished, we kayaked, we sat around the fire pit, we enjoyed the screened porch. My only complaint would be that I mistakenly thought the cabin would be a little more secluded but even with that being said, it was quiet, it was serene, we enjoyed our long weekend very much and are talking about another trip there. And Gloria is a great hostess. We were pleasantly surprised at how nice everything was.

Swordfish Suite - Pup Shed Retreat
Awesome place with tons of great outdoor activities. Nice community with good public spaces. Comfy beds, great ac, easy access to amenities. Pup shed was a great additional space. Host very prompt to communicate as well. Would definitely stay again!

Cozy Cottage w/ Fireplace & Private Yard
The interior of this home was freshly renovated and was spotless inside. We loved the property and fenced in yard so our dogs could enjoy the stay, too. Exterior of the home could use some TLC - especially considering the price we paid to stay here during non-peak lake season. We loved our stay and would certainly entertain coming again.

The Someday Lake House at Tims Ford Lake
beautiful home!! everything was as it should be. we were very comfortable for our stay.

Chattanooga River Escape
Beautiful and peaceful setting. Clean and updated with everything you need inside. Great deck for relaxing. We love the water and the kayaks were great. We drove to multiple waterfall hikes that were amazing. would stay again.

Lakeside Family Fun Retreat!
Everything was as expected and descriptions were accurate, which we appreciated. Shannon was proactive provided us with information before we needed to ask. There were no frills and that’s what we were looking for. However, don’t let the “no frills” keep you from thinking this is a good place to spend time. You have everything that you would need!
Cabin rentals with a kayak

Eagle Lake Cabin Coalmont
Good communication and perfect locations for a bachelor party. Just good, clean fun, fishing, kayaking and having a space to cook and hang.

Atypical Cabin with amenities near Sewanee
Perfect for a weekend getaway!

Cabin at Normandy Lake
Susie's place was quiet, exceptionally well stocked and very comfortable. We were looking for a place that we would feel comfortable in...sitting outside reading a book or cooking a meal on the bbq. This was a very good choice. The walk to the was mostly shaded and the road was quiet, even on Labor Day weekend. The lake and the campground is clean with plenty of picnic tables. We were very pleased with Susie's cabin.

Sunflower Shores Log Cabin Dunlap Tn Deerhead Lake
This is my third time to stay here- one time with family and this second time with friends. The cabin is cute and the location rat the water is lovely and relaxing. Beth provided some snacks and spaghetti and other breakfast food to make like oatmeal and pancakes. It’s a great place for a relaxing retreat. Thank you again!

Eco Container Cabin
we stayed in the Eco Container home. It was really cool. Our power went out from a bad thunderstorm storm but that was no problem because the container home was equipped with a solar powered battery back up. The location was very nice, remote but easy to find and just 10 minutes from town. Millers waterfall was beautiful and serene. Check out was very personal. We shared hiking stories and other stories of the property. I love this place. I would recommend to anyone who loves hiking and nature or just a place to relax and get away from the rat race.

Secluded 1930s Wooded Lakeview Fishing Cabin!
Awesome cabin and property! Very comfortable and perfect place to unplug and enjoy nature. We loved the front porch and bird watching. Very clean and charming. We had everything we needed and the host was very responsive and answered our questions promptly. Would stay here again!

Lakefront Cabin w/ Serene Views & Kayaks
2nd visit at this lovely gem. This was a relaxing getaway for myself and a girlfriend. We enjoyed the peace and quiet, even took the kayaks all around Bedford Lake Saturday. I will be returning for another visit as soon as schedules allow.

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
Quiet location, plenty of space for our family. Hosts were extremely responsive and helpful. The house was clean and had everything we needed.
Quick stats about vacation rentals with a kayak in Winchester
Total rentals
20 properties
Nightly prices starting at
G$23,006 GYD before taxes and fees
Total number of reviews
530 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Tennessee Aquarium
- Cloudland Canyon State Park
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- Chattanooga Golf and Country Club
- The Ledges
- Chattanooga Choo Choo
- Coolidge Park
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- Old Fort Golf Course
- The Lookout Mountain Club
- National Medal of Honor Heritage Center
- Hunter Museum of American Art