Vacation rentals with a kayak in Winchester

Find and book unique kayak rentals on Airbnb

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Popular amenities for Winchester kayak rentals

House rentals with a kayak

Top guest favorite
Home in Winchester
5 out of 5 average rating, 12 reviews

Barefoot Dreams

JohnRating, 5 stars3 weeks ago
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.
Top guest favorite
Home in Tullahoma
4.98 out of 5 average rating, 60 reviews

Beautiful cottage next to Tims Ford Lake

LaurelRating, 5 stars1 day ago
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!
Top guest favorite
Home in Winchester
5 out of 5 average rating, 40 reviews

Tims Ford *FreeUTV/kayaks/canoe*2.5 acres/private

MartinaRating, 5 stars4 weeks ago
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.
Top guest favorite
Home in Winchester
5 out of 5 average rating, 14 reviews

Lakeside Serenity: Cove Retreat

ElaineRating, 5 stars5 days ago
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 !!!!
Guest favorite
Home in Whitwell
4.91 out of 5 average rating, 120 reviews

Blue Heron Lake House

JanetteRating, 5 stars3 weeks ago
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!
Top guest favorite
Home in Winchester
5 out of 5 average rating, 15 reviews

Tennessee Pearl: lakefront-amazing views-lake toys

Christy E.Rating, 5 stars2 weeks ago
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!
Top guest favorite
Home in Tracy City
5 out of 5 average rating, 57 reviews

Catch & Release - Spacious Lakefront Getaway

AnneRating, 5 stars3 weeks ago
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!
Top guest favorite
Home in Winchester
4.95 out of 5 average rating, 42 reviews

Grand Lakeview: Double decker dock, Fire Pit, Spa

JulieRating, 5 stars3 days ago
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

Guest favorite
Cottage in Kelso
4.97 out of 5 average rating, 78 reviews

Bluebird Rest- Peaceful Lake Retreat

DanielRating, 5 stars2 days ago
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!
Guest favorite
Cottage in Winchester
4.93 out of 5 average rating, 15 reviews

Lake it Oar Leave it- Lakefront on Tim's Ford Lake

LanceRating, 5 stars6 months ago
worked over very well. Spoke with Tara about the upstairs heat unit, breaker was tripping or not functional
Top guest favorite
Cottage in Kelso
5 out of 5 average rating, 24 reviews

Clementine Cottage

DarleneRating, 5 stars10 months ago
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.
Guest favorite
Cottage in Tracy City
4.97 out of 5 average rating, 58 reviews

Swordfish Suite - Pup Shed Retreat

JeffRating, 5 stars6 days ago
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!
Cottage in Estill Springs
5 out of 5 average rating, 8 reviews

Cozy Cottage w/ Fireplace & Private Yard

JoshuaRating, 5 stars17 months ago
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.
Cottage in Winchester
4.88 out of 5 average rating, 26 reviews

The Someday Lake House at Tims Ford Lake

RobertRating, 5 stars6 months ago
beautiful home!! everything was as it should be. we were very comfortable for our stay.
Cottage in Whitwell
4.7 out of 5 average rating, 159 reviews

Chattanooga River Escape

CraigRating, 5 stars1 month ago
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.
Guest favorite
Cottage in Tullahoma
4.99 out of 5 average rating, 85 reviews

Lakeside Family Fun Retreat!

DestinyRating, 5 stars1 week ago
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

Superhost
Cabin in Coalmont
4.81 out of 5 average rating, 31 reviews

Eagle Lake Cabin Coalmont

KristopherRating, 5 stars1 month ago
Good communication and perfect locations for a bachelor party. Just good, clean fun, fishing, kayaking and having a space to cook and hang.
Cabin in Monteagle

Atypical Cabin with amenities near Sewanee

MollyRating, 5 stars4 months ago
Perfect for a weekend getaway!
Top guest favorite
Cabin in Manchester
5 out of 5 average rating, 25 reviews

Cabin at Normandy Lake

JonRating, 5 stars3 weeks ago
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.
Guest favorite
Cabin in Dunlap
4.96 out of 5 average rating, 138 reviews

Sunflower Shores Log Cabin Dunlap Tn Deerhead Lake

JamieRating, 5 stars2 weeks ago
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!
Superhost
Cabin in Tracy City
4.91 out of 5 average rating, 385 reviews

Eco Container Cabin

ChrisRating, 5 stars1 week ago
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.
Top guest favorite
Cabin in Beersheba Springs
4.96 out of 5 average rating, 47 reviews

Secluded 1930s Wooded Lakeview Fishing Cabin!

JohnRating, 5 stars2 weeks ago
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!
Guest favorite
Cabin in Wartrace
5 out of 5 average rating, 10 reviews

Lakefront Cabin w/ Serene Views & Kayaks

NicoleRating, 5 stars2 weeks ago
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.
Guest favorite
Cabin in Winchester
4.95 out of 5 average rating, 64 reviews

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

JulieRating, 5 stars1 month ago
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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