Family-friendly holiday rentals in Winchester

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Top-rated family-friendly rentals in Winchester

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in Dunlap

4.92 out of 5 average rating, 237 reviews

Cagle Mountain Cabin near Fall Creek Falls Park TN

Quiet, comfortable and contemporary cabin on 7 acres, situated between three of the most beautiful parks in Tennessee: Fall Creek Falls, Savage Gulf and Rock Island State Park. We are pet friendly for a small additional fee. *** We have made the difficult decision to sell our cabin. Any accepted reservation will be honored, but it may be necessary to show the home to a potential buyer during your stay; you will be notified a minimum of 24-hours in advance if this happens during your stay. **

Top guest favourite

Home in Lookout Mountain

5 out of 5 average rating, 111 reviews

Eden in the Clouds

No pets/ smoking allowed for the comfort of all our guests. Min. age 25 to rent per insurance req. This beautiful single family home is located on the edge of the West Brow on Lookout Mountain,GA. It is a 3 bedroom , 2 1/2 bath , 2 story home with decks overlooking the valley on both floors. All 3 bedrooms are upstairs. It is perfect for a family vacation or a group getaway. You can park in the single car garage. Rock City & Ruby Falls are a 7 mile drive and downtown Chattanooga is 14 miles.

Guest favourite

Home in Winchester

4.94 out of 5 average rating, 108 reviews

Beautiful Tims Ford lakefront home

Beautiful 3 level lake front home right by the water with no steps to the dock. Plenty of room for large groups of people and great for families with kids. Five bedrooms with a bonus room that has plenty of extra beds. Located less than a mile from public boat ramp. Located in quiet cul-de-sac, on a cove with no wake next to the main channel. If there are any dates that are blocked off that you want please message us because we may have some blocked off dates that we can open up for you.

Top guest favourite

Home in Winchester

4.96 out of 5 average rating, 119 reviews

Private dock/gazebo on quiet cove. Tims Ford Lake!

Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

Top guest favourite

Cabin in Altamont

4.97 out of 5 average rating, 320 reviews

Sunrise Mountain Tree House Cabin

Experience the fun of living among trees in our treehouse mini-lodge feel check out 2 other cabins Patriot's Retreat & Sunrise Mtn Cabin. Our tree house is extremely comfortable, with a view of the Cumberland mountains. Complete with a full kitchen, bathroom, two-loft sleeping and viewing areas. Several major state parks/hiking within a few miles of the cabin. Exceptional star viewing. The cabin has fiber optic WiFi which is not shared. Pet cats are not allowed as we are allergic.

Superhost

Cabin in Chattanooga

4.8 out of 5 average rating, 304 reviews

Cozy Mountain Retreat w/ Spa

20 min. from downtown Chattanooga This cabin is surrounded by woodlands. Hiking trails, swimming holes and water falls abound here! End the day in the mountains gazing at the stars from the spa, or gathered around the fire roasting marshmallows. This adorable cabin sleeps 6 comfortably and provides a full kitchen, sleeping quarters separated by barn doors for the kids, and a private back yard with patio and grill for your enjoyment. No smoking or vaping NO KIDS ALLOWED IN HOT TUB

Guest favourite

Cabin in Bryant

4.88 out of 5 average rating, 103 reviews

Elk Ridge No Sunday Check In 25 mi fromChattanooga

WE DO NOT HAVE SUNDAY CHECK INS , I HAVE 9 CABINS IF THIS ONE IS BOOKED YOU CAN SEE OTHER AT WWW.GRANTSUMMITCABINS.COM you have all the amenities of home. real wood fireplace, hot tub, washer and dryer, full kitchen,amazing views, private, gated , i have 8 cabins close to each other. pictures just do not describe the quietness and serenity of the place. only 25 miles to downtown chattanooga tn. located on the tn ,ga, and alabama lines. we are not a bed and breakfast

Superhost

Cabin in Winchester

4.82 out of 5 average rating, 157 reviews

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

Top guest favourite

Cottage in Fayetteville

4.97 out of 5 average rating, 234 reviews

Country Cottage Hideaway near Lynchburg

Recently remodeled Farmhouse on a working goat farm. The rental does not include access to the Barn or farm land. Visiting Lynchburg? This is the perfect place to unplug and enjoy quiet country living. The property is tucked into a secluded country hollow and does not have any visible neighbors. Includes a large porch with a swing and a cozy fireplace to snug in front of on those chilly winter nights. Located 7 miles from Jack Daniel's and Downtown Lynchburg Tennessee.

Guest favourite

Guest house in Dunlap

4.98 out of 5 average rating, 191 reviews

The Bird House near Fall Creek Falls State Park

This is a 1080 sq ft, 2 bedroom / 2 bath pet friendly (see details below for pets) house with a gas grill, fully equipped kitchen, fully stocked beverage station that host a coffee pot and Keurig, snacks, laundry with detergent, and a fire pit. Apple TV, WiFi, books, and board games. Fur babies are welcome, though please read through all the rules regarding pets. Please note there is a pet fee. Special note: the house will be decorated for the holiday season!

Guest favourite

Home in Lookout Mountain

4.84 out of 5 average rating, 173 reviews

7 Bdrm🎖22ppl~LktMtn 1 mile to RockCity

5 KING BEDS 2 QUEEN 8-9 SINGLES (24ppl MAX) Ping-pong, FUSBOL 4 miles to dwntn Chatt.Well-appointed, home in upscale, high-end quiet neighborhood on 3acres! NO ANIMALS AT423 🙏🏼802.1965ALL ! New BLACKSTONE 36” Castiron GriddleGrill on patio! 🎶 MUSIC INSIDE only 24/7!! * Registered guests only Enter CORRECT Guestcount 2LargeRefrigerators. 1 mile to RockCity, InclineRailway next to Covenant 10CAR max 3 lg HOUSES downroad if need space

Top guest favourite

Cabin in Lookout Mountain

4.98 out of 5 average rating, 378 reviews

The Magic Treehouse

Cozy and spacious cabin at the top of Lookout Mountain, GA. Enjoy the woodsy scenery and outdoor activities around Lookout. Close to hiking and biking trails, hang gliding, rock climbing, and many other outdoor activities. It is only 20 minutes from downtown Chattanooga. There is plenty of room on both decks for bikes or hang gliding equipment and anything else you might want to bring.