Kid-friendly vacation rentals in Winchester

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Top-rated kid-friendly rentals in Winchester

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

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Guest favorite

The tiny house is set among trees, featuring a wooden deck with railing and stairs leading to the entrance. Expansive windows allow natural light in, and the surrounding foliage enhances the cabin's secluded feel.

Tiny home in Chattanooga

4.95 out of 5 average rating, 395 reviews

La Cabaña You have to climb it to get the wooness!

Pets welcome with a $35 per pet fee to a maximum of 2. Quiet mountainside tiny house on 2.5 acres in the Tennessee River Gorge will provide you with the best nights sleep. Spectacular bluff view hikes are within a few miles of the cottage. Enjoy kayaking or stand up paddle boarding along the Tennessee River with 2 rental locations within a 3 minute drive of the house. With the convenience of downtown Chattanooga only a 15 minute drive you can't miss out on everything this rental has to offer.

Top guest favorite

The dining area features a spacious table with elegant white chairs, set for six. Above, a sparkling chandelier illuminates the space, complementing the dark blue curtains. The open kitchen is visible in the background, showcasing modern appliances and ample counter space.

Home in Lookout Mountain

4.99 out of 5 average rating, 119 reviews

Dog/Family Friendly Mountain Gem near Attractions

Looking for a family and pet-friendly getaway? Look no further than The Sweet Retreat! Your cozy and comfortable vacation rental is located just off Scenic Highway and close to popular attractions, including Ruby Falls, Covenant College, Rock City, and 8 miles to Chattanooga. You'll love our high-speed internet, comfortable beds, multiple TVs, stocked kitchen, fenced yard and outdoor fire pit. With so much to see and do in the area, you'll love making The Sweet Retreat your home away from home.

Top guest favorite

An open concept living space features a large kitchen with modern appliances, including a spacious refrigerator. A dining table is positioned near a window, and a comfortable seating area is visible with a television mounted on the wall. Natural light enhances the warm, neutral tones.

Home in Lookout Mountain

4.97 out of 5 average rating, 143 reviews

Open concept, peaceful porches, quiet, clean !

Quiet, wooded, peaceful, spacious home on Lookout Mountain. Open concept floor plan with full laundry. Fully furnished kitchen for those that like to cook with a large refrigerator and dishwasher as well as an island with extra seating. Each bedroom has at least one large bed and TV. Large screen TV in family room.All TV's include Netflix.There is an outdoor basketball hoop, grill and lots of parking. Chattanooga is only 10-12 miles away. Near hiking, hang gliding, rock climbing and Rock City.

Top guest favorite

Home in Chattanooga

4.98 out of 5 average rating, 121 reviews

The Jade | HotTub & Pool, Family Friendly Stay

Located in the heart of Historic Saint Elmo, 10 mins from Downtown Chattanooga (Tennessee Aquarium), the trendy Southside (Chattanooga Choo Choo), Ruby Falls, Rock City, & Incline Railway. Unwind and connect with friends and family in our insta-worthy, beautifully designed home. Easily walkable to food & drinks or coffee & ice cream. Over 2250 sq ft, comfortably sleeps 10 adults in 4 bedrooms/ 3.5 bath. A 5 person hot tub, 30 ft pool, ping pong table, yard games, a private bar, and fire pit!

Top guest favorite

A spacious bedroom features a queen bed with a striped blanket. A mural depicting mountains adds color to one wall. Additional furniture includes a dresser and a blue seating area with a decorative pillow. Soft lighting is provided by two bedside lamps.

Guest suite in North Chattanooga

4.95 out of 5 average rating, 242 reviews

Spacious Apt Near Bridge w/Fast Wifi, Parking

Excellent location (8 min downhill walk to Frazier St and Pedestrian Bridge) in the most desirable neighborhood in Chattanooga. Safe and serene, with nearly 1000sq ft. of living space. Blazing fast and reliable WiFi (typically 100-400Mbps). Dedicated parking (up to 2 mid-size cars), full fridge and microwave, washer/dryer, and plenty of privacy and convenience. Coffee machine (with Starbucks coffee pods) included. Please note this basement apartment does NOT have a full kitchen (see pics).

Top guest favorite

A closet space features a compact pack-and-play, ideal for children, positioned on soft carpet. Adjacent to it, a high chair is stored, alongside wooden storage units and a clothing rack with hangers.

Condo in Chattanooga

4.96 out of 5 average rating, 153 reviews

Chattanooga Escape! Riverwalk, Aquarium & More

Enjoy our modern, well-equipped 2 bedroom, 2 bathroom condo for minimum 3-night stays. Enjoy easy access to everything downtown Chattanooga has to offer! Just across the street from the Tennessee Riverwalk. Walk to Southern Belle Riverboat (12 min), Ironman staging (11 min), Playground (13 min), Aquarium & IMAX (19 min< 1 mile) and nearby: Creative Discovery Children's Museum, Restaurants, more. There are two restaurants across the street (Parkway Pourhouse and Scottie's on the River).

Guest favorite

A playground structure is nestled among trees with autumn leaves covering the ground. The design includes a green slide, climbing wall, and wooden platforms, offering a fun space for children to play in a natural setting.

Home in Tracy City

4.96 out of 5 average rating, 103 reviews

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

New 2 bedroom cabin in the Water's Edge community. Spacious family room to enjoy fireplace, TV, and dining area. Private hot tub! Master bedroom has a king sized bed. The second bedroom has 2 twin bunk beds, trundle, and a loft. Outdoor living space patio with a grill, table, couch, and firepit. Multi video game system. There is a community lake, playground, and hiking trail. We have two stand-up paddle boards, 1 adult kayak, and 1 child kayak. Pack n' play and high chair available.

Guest favorite

A charming cottage is presented with a light blue exterior, white railings, and a metal roof. Seasonal shrubs are situated in front, with a wooden fence enclosing the yard. Stairs provide access to the entrance, highlighted by a star decoration above the door.

Home in Lookout Valley

4.91 out of 5 average rating, 286 reviews

Star Cottage 1

Cute cottage at the foot of Lookout Mountain. Five miles to downtown Chattanooga and close to popular attractions. There are hiking and biking trails nearby and an easily accessible boat ramp at TVA. You will be just minutes from the freeway and there is a Walmart and restaurants just down the road. Family and pet friendly. Stocked with most of everything you will need for a great vacation! *Please pre-approve pets. We like to know the breed and that they are fully house trained.

Superhost

The exterior of a two-story cabin is seen, featuring a sloped roof and a welcoming front porch with two chairs. Surrounding the cabin, a well-maintained lawn and gravel pathway create an inviting atmosphere amidst a wooded landscape.

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 favorite

A modern kitchen features a long island with eight turquoise high-back stools. Stainless steel appliances complement crisp white cabinetry, and light wood flooring adds warmth. Large windows provide natural light and views of the outdoor greenery, enhancing the open layout that connects to a living area.

Home in North Chattanooga

4.99 out of 5 average rating, 126 reviews

Delmont | Downtown Walking Distance | Rooftop Deck

Amazing, Modern home that is walking distance to Northshore and Downtown! Unbelievable location right downtown in Chattanooga's Northshore. This property features walkability to Shopping, Coolidge Park, Tennessee River Aquarium, Restaurants and more! This home has a modern flare with extremely open floorplan and spacious bedrooms. Technology galore with keyless access, voice enabled lighting, lightning fast fiber optic internet with WiFi, and multiple HD flat panels.

Top guest favorite

A clean and functional bathroom features a white subway tile shower area and a light-colored bathtub. A bright yellow and gray patterned shower curtain adds a pop of color, while toiletries are neatly arranged on a wall-mounted shelf.

Condo in Chattanooga

4.96 out of 5 average rating, 449 reviews

Stylish & Family-Friendly Downtown Condo with Pool

Retreat from your Chattanooga adventures to our downtown condo with comfortable furnishings, homey touches, and a corner for the kids with books and toys. Order in and watch Netflix on the couch or cook a family meal in the fully-equipped kitchen (kids' dinnerware included). Perfect for a family, two couples, or small group of friends, the condo has a shared gym, pool, & fire pit. This is the perfect base camp to check out all that Chattanooga has to offer!

Guest favorite

The charming exterior of the cottage features a sloped roof and wood-paneled walls, adorned with flower boxes filled with sunflowers. A bright red door serves as the focal point, complemented by rustic seating and warm outdoor lighting against a backdrop of lush greenery.

Home in Chickamauga

4.95 out of 5 average rating, 565 reviews

Fairy Tale Cottage

Our Fairy Tale Cottage offers a magical escape from the hustle and bustle of everyday life while embracing the cozy nostalgia and comforting classics you know and love. This storybook getaway is perfect for nature lovers, writers, romantics and families with children over 5 years old seeing a touch of magic in their lives. Enjoy the quiet countryside and watch movies, play games or even play dress up!