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Family-friendly holiday rentals in Ashland

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Ashland

  • Total holiday rentals

    Explore 60 holiday rentals in Ashland

  • Nightly prices starting at

    Ashland holiday rentals start at $78 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,450 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Ashland holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ashland rentals

  • 4.9 Average rating

    Ashland stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated family-friendly rentals in Ashland

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

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Guest favourite
Home in Portsmouth
4.98 out of 5 average rating, 106 reviews

Pink Dreams Cottage: Hot Tub, Fire Pit, BBQ & More

Welcome to Pink Dreams Cottage – a one-of-a-kind, fully renovated pink paradise! This gorgeous cottage was lovingly transformed by a father & daughter duo from an abandoned house to a picturesque pink cottage that’s perfect for your next getaway. Whether it’s a special occasion, a girls weekend, a romantic getaway, or a creative escape, this is the perfect place to make memories that will last a lifetime. Come experience the magic of Pink Dreams Cottage and make your pink dreams come true!

Guest favourite
An open concept living space features a sectional sofa with a coffee table, offering floor-to-ceiling windows that showcase city views. Modern kitchen appliances and a dining area with seating are visible. Sleek light fixtures enhance the welcoming atmosphere.
Loft in Ashland
4.95 out of 5 average rating, 376 reviews

Sky Loft on 10 . 2 bed . 2 bath + Modern luxuries

Lay your head in the clouds. Sky Loft on 10 is a brand new, state-of-the-art loft furnished with modern luxuries. It is conveniently located in the center of the city blocks away from downtown, Paramount Arts Center, KDMC, Central Park and the Ashland Town Center Mall. Tenth floor views and access to two private balconies provide stunning views of the city, riverfront and Tri-State area. Perfect for hosting or a relaxing getaway. Your next stay, retreat or celebration is just on the horizon.

Top guest favourite
Home in Russell
4.98 out of 5 average rating, 408 reviews

River & Bridge view - HotTub, CoolingTub & MistFan

Enjoy a hot-tub, cooling tub and misting fan during the summer. The river & bridge views are magical & soothing to the soul. Make your way into the backyard & you will quickly forget that you are in an Eastern KY residential area. It’s often stated by our guests that the view rivals some of the top landscapes & city skyline from around the world. You can walk to downtown Russell & enjoy shopping, great food & tasty drinks. Only a few mins from Ashland KY & 20 mins to Huntington, WV

Top guest favourite
The exterior of a red brick home is depicted, featuring a sloping gray roof and a driveway leading to a garage. An American flag is displayed outside, complemented by a neat garden of colorful flowers and lush greenery flanking the entrance.
Guest suite in Ashland
4.99 out of 5 average rating, 171 reviews

Cozy, newly remodeled, extra large 2 bdrm basement

Beautiful home in a very nice, quiet neighborhood. Close to downtown Ashland (3 miles) and I-64 (5 miles). This is a full size newly remodeled basement with it's own outside entrance. Great host and great setting. Access to the beautiful back yard, kids gym, gazebo, grill and covered patio. The basement has large windows in the bedrooms and queen beds. Located 8 minutes from King’s Daughters Hospital and 30 minutes from Huntington, WV hospitals. Long term travel workers welcome.

Top guest favourite
A small wooden cabin features a light wooden exterior with a green roof. A front porch is accessed by three steps, providing a welcoming entrance. One window is visible on either side of the door, surrounded by grassy areas and trees in the background.
Cabin in Carter County
4.98 out of 5 average rating, 112 reviews

Cabin at Cabin Creek Campground

Private cabin located in campground close to bathhouse. A/C and electric fireplace. Porch swing, fire ring, & picnic table for your outside enjoyment. Queen size bed with full size bed in loft overhead. Microwave & small refrigerator. Dining table with 3 benches. Comfortable sitting chair with footstool. Fishing included in our 12-acre lake. Walking path runs the length of the campground. Bring bed linens (sleeping bag or blanket/sheet) & pillow, bath linens (towels/washcloths).

Top guest favourite
The living room features a dark gray sofa, complemented by decorative pillows. A lamp provides soft lighting next to the window, which is adorned with light curtains. The entry door is visible, along with a glimpse of the adjoining kitchen and dining area.
Bungalow in Ashland
4.96 out of 5 average rating, 190 reviews

Roosevelt Retreat II - 1BR Queen/1BA

Keep it simple at this peaceful 1 queen bedroom, 1 bath home with a sofa in the living room. The kitchen is furnished with a full size refrigerator, stove, and fully stocked coffee bar. This quiet, private home is 1 of 2 on the property and it is located at the back of the property. There are 2 flat screen TV’s in the bedroom & living room with high speed wifi. You will enter in the alley behind the house with 1 car parking available right outside your door. *** PET FEE APPLIES***

Top guest favourite
A wooden signpost displaying directional arrows to various local attractions. The sign's placement allows for easy visibility, with distances specified to nearby places of interest, such as Market St. Café and Portsmouth Brewery Co. The rustic building in the background complements the sign.
Tiny home in Portsmouth
4.97 out of 5 average rating, 241 reviews

Charming Tiny Space/ Modern Minimalist

This unique place has a style all its own in a perfect tiny space. Snuggle into a perfect getaway or extended stay. Located in downtown Portsmouth within walking distance to Marting’s Event, Vern Riffe Performing Arts Center, Ohio River, Historic Boneyfiddle District with many antique shops and restaurants. Great place to jump on your bike and travel around. Wonderful things to do and see.

Guest favourite
A welcoming exterior of a single-story home is shown, featuring a front porch with a door framed by stone accents. An American flag adorns the porch, while a small tree and landscaping enhance the natural surroundings, with wooded greenery in the background.
Flat in Ashland
4.88 out of 5 average rating, 219 reviews

Cozy, comfy and private-2 miles from the Casino

Cozy, Country setting. Very neat and clean 2 bedroom apartment with two queen beds. Country feel but close to all the necessities. You have the property to yourself and there's lots of parking. You are just minutes from Walmart, Dollar General, fast food and local restaurants. This property is just 15 minutes from Rush Off Road with easy parking for trucks and trailers.

Guest favourite
A well-equipped kitchen features light gray cabinetry and black countertops, complemented by a white tile backsplash. Essential appliances include a refrigerator, stove, and microwave. Shelves hold various pantry items and a bowl of bananas, while a sink area offers convenience for meal preparation.
Home in Ashland
4.9 out of 5 average rating, 299 reviews

COZY, QUAINT AND CLOSE TO TOWN!

COZY, QUAINT, AND MINUTES FROM DOWNTOWN. This is a newly remodeled three bedroom home. Very spacious with off street parking. All wood floors and nicely tiled shower. Two queen size beds in bedroom one and two. Bedroom three is vacant. Large eat in kitchen, washer and dryer, side and front entrance. Small private back yard.

Guest favourite
The welcoming porch features a classic white rocking chair and a vintage yellow bicycle. A potted yellow plant and two colorful flower arrangements add charm. The door is adorned with a seasonal wreath, enhancing the friendly exterior.
Home in Ashland
4.89 out of 5 average rating, 350 reviews

Hampton Cottage

Newly renovated 2 story 2 bed 2 Bath located within 10 minute driving distance to Kings daughters Medical Center & Central Park. Perfect neighborhood for children to play or ride bikes. Within 10 minutes of Ashland Town Center and all major restaurants. Private off street parking in extremely family friendly neighborhood.

Guest favourite
The living area features a welcoming orange accent wall with a decorative sign and a lamp on a side table. A dark sofa with patterned cushions faces a circular coffee table. A dining area is visible in the background, illuminated by natural light from a nearby window.
Cabin in Greenup
4.98 out of 5 average rating, 126 reviews

White Oak 2-bedroom cabin along the Little Sandy

Relax with the whole family or a few friends in our off the beaten path cabin nestled along the Little Sandy River. Bring a kayak or some fishing gear and enjoy the quiet seclusion of The White Oak Cabin. You are surrounded by the wilderness but still close enough to take the family out for a movie.

Superhost
An authentic log cabin is surrounded by greenery, showcasing wooden logs and a charming porch with support beams. A brick pathway leads to the entrance, while a gentle lawn extends around the structure, providing a secluded, natural setting.
Cabin in South Shore
4.87 out of 5 average rating, 406 reviews

Historic log cabin

Authentic historic log cabin sitting on 6+ acres with a private pond. The cabin and its surrounding environment creates the feeling of being secluded yet you have the safety of neighbors. You’ll find this little hidden treasure to be your perfect getaway for fun and relaxation!

Popular amenities for Ashland family-friendly rentals

When is the best time to visit Ashland?

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Avg. price$129 SGD$116 SGD$131 SGD$125 SGD$131 SGD$131 SGD$145 SGD$124 SGD$144 SGD$119 SGD$129 SGD$131 SGD
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