Holiday rentals in Ashland

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Top-rated holiday rentals in Ashland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Russell
4.98 out of 5 average rating, 393 reviews

Home w/a River & Bridge view, a HotTub & an Igloo

RIVERTIME - A house w/a hot-tub & an igloo. Experience it all on the bank of the Ohio. The 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

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
4.96 out of 5 average rating, 361 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.

Superhost
Cabin in McDermott
4.86 out of 5 average rating, 500 reviews

The Roundabout Cabin near Portsmouth, Ohio

Nestled on 4 wooded acres along Pond Creek, this one of a kind cabin will certainly be a unique experience. Walls of windows blur the lines between inside and out, connecting you with nature in every room. The house is very open, with rooms winding around the central stone fireplace with varying levels. The kitchen is stocked with supplies for preparing your own meals, but downtown Portsmouth restaurants are just 10 minutes away. Outside are patios for relaxing and woods for walking.

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
5 out of 5 average rating, 154 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 cozy living area features a stylish sectional sofa with decorative pillows, complemented by a modern electric fireplace underneath a mounted TV. Large windows allow natural light to fill the space, while elegant curtains and a chandelier add a touch of sophistication.
Flat in Ashland
5 out of 5 average rating, 57 reviews

Comfort & convenience in beautiful 3BR apt.

Newly renovated upscale 3 BR apartment located in the heart of downtown Ashland perfect for business travelers, visiting family and friends, staycation, weekend getaway, or a cozy home base on your next visit to Ashland, this is the perfect gathering place. It has all the perks and conveniences of a hotel, with the comforts of home. Located within 3 blocks of 16 restaurants, Ashland riverfront, Paramount, shopping, Central Park, Highlands Museum, Broadway Square, and the Delta hotel.

Top guest favourite
A spacious bedroom with a large bed covered in neutral bedding lies on a vibrant area rug. A ceiling fan rotates above, and a floor lamp provides soft illumination. Decorative plants and artwork enhance the room's design, while a dresser and mirror add functionality.
Flat in South Point
5 out of 5 average rating, 17 reviews

“C” Ya Soon Abode

This stylish place is perfect for work trips, time alone or just a home away from home while visiting family or the area. We are centrally located between Huntington, WV and Ashland, Ky. Spacious rooms, amenities, stylish decor & cleanliness are just a few reasons to stay with us. Wifi, laundry, designated parking, a work/study area & a fully functional kitchen are a few more. Whether you’re attending a concert or here for work, you’re sure to be comfortable. We hope to “C” ya soon!!

Guest favourite
A spacious living area is filled with natural light, featuring a comfortable leather sofa and armchair. A wood coffee table sits in the center, with decorative items placed atop it. A tall floor lamp and a potted plant add warmth, complemented by a soft area rug.
Flat in Ashland
4.96 out of 5 average rating, 102 reviews

Blanc Space - South Ashland

Welcome to Blanc Space A bright & modern apartment in historic South Ashland building. A balanced blend of style and convenience with a vintage touch. Our space is designed with your relaxation in mind, airy & spacious interiors, flooded with natural light, creating a serene ambience throughout. Located just minutes from downtown, you'll have easy access to: -shops -dining -local festivities -The Paramount Arts Center -Kings Daughters Hospital We can't wait to welcome you!

Superhost
A spacious living area is furnished with soft, neutral-toned sofas accented by decorative pillows. The room features a decorative globe on the coffee table, and a well-lit kitchen can be seen in the background, showcasing modern cabinetry and open shelving.
Bungalow in Ashland
4.89 out of 5 average rating, 106 reviews

La'Chic Bungalow Modern 3 Bed/1.5 Baths

Come, relax and enjoy this beautifully renovated 1921 French Bungalow with high end furnishings including Restoration Hardware sofas, World Market bar and dining chairs, Ethan Allen cabinetry and Magnolia Home accents. A unique blend of Industrial Farmhouse and vintage decor that's sure to please all guests. Conveniently located on a quaint charming culldesac only 2 miles from downtown Ashland, local restaurants, hospital, Museum, Paramount, town mall, Sandy's casino, and park.

Guest favourite
A living room space features a brown sectional couch positioned around an extendable coffee table. Sunlight filters through windows adorned with white blinds, and a ceiling fan provides ventilation. Wall decor includes welcome signs and decorative metal wall art.
Home in Ashland
4.96 out of 5 average rating, 166 reviews

Roosevelt Retreat - 2BR, 2 Bath Craftsman

Charming, updated Craftsman in South Ashland which is 1 of 2 on the property (home located at the front of the property). You will find a 2 bedroom (1 king, 1 full bed/1 xl twin bed), 2 bath (one bathroom contains the washer and dryer), fully furnished kitchen, living room with sectional, and 3 flat-screen smart TV's. This is a quiet, residential neighborhood within a 10-minute walk of Putnam Stadium and a 5 -minute drive to downtown. NO SMOKING - NO ANIMALS

Top guest favourite
A charming cabin is set amidst a wooded landscape, featuring a wooden deck with decorative plants. Steps lead to the entrance, flanked by seasonal decorations. The exterior showcases a combination of log and panelled walls that blend harmoniously with the surrounding nature.
Cabin in Catlettsburg
4.95 out of 5 average rating, 110 reviews

Cozy and Private - Long Bottom Cabin

The perfect peaceful family getaway! Experience the beautiful hills of Kentucky. Enjoy listening to the birds especially the Whippoorwills. Roast hotdogs and S’mores on the fire while gazing at the stars. You may experience some wild life, too! Private and quiet. Traveling US 23 or I64? It’s a great stopping place. 10 miles to Rush Off Road 22 miles to The Paramount Arts Center 15 miles to Camp Landing Entertainment District 23 miles to Yatesville Lake

Top guest favourite
An open living area features a brown leather sectional sofa facing a modern electric fireplace beneath a large wall-mounted TV. Floor-to-ceiling windows invite natural light, while decorative vases enhance the minimalist decor. A spacious kitchen area is visible in the background.
Apartment in Ashland
4.99 out of 5 average rating, 94 reviews

The Skytower Penthouse - Suite 1

Nestled at the top of the tallest mixed use tower in downtown Ashland, KY guests will find an upscale condo that boasts the best views in the Tri-state area. The unit's central location provides guests with easy access to restaurants, theaters, shopping, UK KDMC & Camp Landing district- the newest gaming and racing venue. M&J Cafe on 1st floor lobby offers light fare & excellent coffee. Unit is accessible 24/7.

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, 288 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.

Popular amenities for Ashland holiday rentals

When is the best time to visit Ashland?

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Frequently Asked Questions

  • What are the best places to stay in Ashland?

    Ashland has comfortable stays in its downtown area, where you can explore local shops and arts spaces easily. For a quieter atmosphere, neighborhoods near Central Park are often suggested for their leafy streets and friendly vibe.

  • What are the best things to do in Ashland with kids?

    Families often enjoy exploring Central Park’s playgrounds, visiting the Highlands Museum and Discovery Center, or catching a show at the Paramount Arts Center. Outdoor spaces, interactive exhibits, and occasional children’s performances create varied options.

  • What are some of the best things to do in Ashland?

    Explore the arts at the Paramount Arts Center, stroll through Central Park’s peaceful paths, or learn local history at the Highlands Museum and Discovery Center. Ashland also has seasonal festivals and markets to discover regional crafts and flavors.

  • How is the weather in Ashland?

    Ashland has cold winters, with January lows around 26°F (-3°C), and warm, humid summers that peak near 86°F (30°C) in July. Rain is frequent throughout the year, and spring brings milder temperatures and blooming landscapes.

  • When is the best time to visit Ashland?

    Late spring and early autumn are often recommended for comfortable temperatures between 46–80°F (8–26°C) and vibrant outdoor scenery. During these times, Ashland has seasonal events and lively local markets.

  • What are the best places to visit in Ashland?

    The Paramount Arts Center, Central Park, and the Highlands Museum and Discovery Center are frequently suggested for art, history, and recreation. Ashland also has galleries, riverfront paths, and music venues around downtown.

  • What are some hiking trails in Ashland?

    Central Park has walking trails shaded by mature trees, while nearby rural areas are known for scenic paths through forests and hills. Locals often explore nature preserves just outside Ashland for a deeper outdoor experience.

  • What are some family activities we can do in Ashland?

    Families can relax in Central Park, engage with interactive exhibits at the Highlands Museum and Discovery Center, or attend a show at the Paramount Arts Center. Outdoor spaces, museum programs, and local performances are frequently suggested.

  • What are some of the best day trip ideas from Ashland?

    Explore nature preserves, visit small towns known for Appalachian culture, or enjoy river activities in communities around the Ohio River. Arts and crafts fairs, historic sites, and forest parks nearby provide new perspectives.

  • Are there any pet friendly accommodations available in Ashland?

    Ashland has pet-friendly stays in residential neighborhoods and around the downtown area. Many local parks, including Central Park, welcome pets on-leash, creating accessible spaces for those traveling with animals.

  • What are some local tips for visiting Ashland?

    Explore downtown on foot to enjoy murals and local shops, and consult the arts center schedule for performances. Pack for changing weather, as rain is common, and talk to locals for recommendations on regional foods and upcoming events.

  • What is Ashland known for?

    Ashland is known for its historic arts venues, lively music traditions, and riverfront heritage. The city has a strong sense of Appalachian culture and frequently celebrates it through festivals and community performances.

  • What are the best hidden gems to explore in Ashland?

    Consider discovering locally owned galleries, quaint shops tucked off the main streets, or mural projects around downtown. Small music venues and crafts markets highlight Ashland’s creative community spirit.

  • What are the best foods to try in Ashland?

    Ashland has Appalachian-inspired dishes, barbecue, classic Kentucky hot browns, and locally baked pies. Many downtown eateries create homestyle meals and regional specialties using seasonal ingredients.

  • What should I bring for a trip to Ashland?

    Pack layers for variable temperatures, a waterproof jacket for year-round rain, and comfortable shoes for walking in parks or downtown. If visiting in summer, lightweight clothing and sun protection are frequently suggested.

  • What is the nightlife in Ashland like?

    Ashland has live music venues, casual bars, and performance spaces concentrated in the downtown district. Locals gravitate toward spots with regional bands, open mics, and occasional arts events in a relaxed, welcoming atmosphere.

  • What are the most popular events or festivals in Ashland?

    Ashland frequently hosts seasonal festivals, concerts in Central Park, and arts events at the Paramount Arts Center. Labor Day weekend and early summer often feature music series, craft fairs, and community celebrations.

  • Are there family friendly vacation rentals in Ashland?

    Ashland has family-friendly vacation rentals in the downtown area and neighborhoods near Central Park. Spacious layouts and easy access to parks and museums make these options attractive for travelers with children.

Quick stats about holiday rentals in Ashland

  • Total holiday rentals

    Explore 90 holiday rentals in Ashland

  • Nightly prices starting at

    Ashland holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    80 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!

  1. Airbnb
  2. United States
  3. Kentucky
  4. Boyd County
  5. Ashland