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, 398 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

Superhost
A well-lit living room features a large, plush sofa and a leather coffee table placed on a textured area rug. A television is mounted above a modern fireplace, while a staircase and a separate dining area can be seen in the background.
Home in Ashland
4.82 out of 5 average rating, 217 reviews

The Roundabout Retreat

Circle back to the "The Roundabout Retreat," a delightful 3BR home a heartbeat away from UK King's Daughter Medical Center. Perfect for families, this gem features a chef-ready kitchen, private fenced yard, plush king bed in a large master, new 58" TVs, office space, and a quaint dining room. Enjoy the convenience of our LG Washtower, a selection of board games for fun evenings, and decor that’s both elegant and welcoming. Your tranquil downtown haven melds style and convenience beautifully.

Top guest favourite
A charming cabin is set amid lush greenery, featuring a rustic wooden exterior and a slanted metal roof. Surrounding trees provide a natural backdrop, and a spacious lawn invites outdoor relaxation.
Cabin in Catlettsburg
4.99 out of 5 average rating, 264 reviews

The Cozy Cabin

Our "Cozy Cabin" getaway is located in a peaceful country setting. A creek & hillside is located behind the cabin. Relax on our 2 porches and enjoy the view of our field with horses grazing and deer passing thru. There is a fire pit, gas grill & small shelter house with swing for your outside enjoyment. All the amenities for a relaxing stay close to Yatesville Lake (18 miles), Rush Off-Road Park (13 miles) & Giovanni's Pizza (5 miles). Tristate area KY/WV/OH can be in all within 30 minutes.

Guest favourite
An open-concept kitchen and living area is displayed, featuring modern fixtures and spacious countertops. Floor-to-ceiling windows allow natural light and provide panoramic city views. A gas-heated fireplace with a sleek design is visible in the background, complementing the contemporary furnishings.
Loft in Ashland
4.96 out of 5 average rating, 365 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.

Guest favourite
Cabin in McDermott
4.86 out of 5 average rating, 505 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.

Guest favourite
A spacious exterior view of a two-story home surrounded by lush greenery. The brick and stone facade is complemented by red accents and multiple windows, allowing natural light to fill the interior. A manicured lawn extends in front, offering a welcoming entrance.
Loft in Ashland
5 out of 5 average rating, 17 reviews

The Haven:Homey Loft in Cozy, Quiet Spot

Take it easy at this unique & tranquil getaway. This spacious, fully furnished 1-bedroom apartment & full kitchen is for traveling professionals, tourists, or a quick get-a-way for some rest & relaxation providing comfort, privacy, & convenience while in Ashland, KY. Enjoy a home away from home offering 1 queen bed, 1 full bed, workspace, cozy living room w/ smart TV & prime subscription, a breezeway with table, relaxing hammock chair, cafe lights, outdoor music available, & pretty views.

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, 161 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 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, 21 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!!

Top guest favourite
Home in Greenup
5 out of 5 average rating, 32 reviews

Victorian Home in Greenup

Whether you are traveling alone or with the whole family, this great place built in 1870 has been completely re-done with lots of room for fun. Enjoy all the comforts of home and explore all that Greenup has to offer within walking distance. There are several festivals including Old Fashion Days, the county fair and spectacular 4th of July fireworks. The city also has a great library with a large genealogy section, a city park with a pickleball court and a boat ramp for river access.

Top 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
4.97 out of 5 average rating, 175 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

Guest favourite
Tiny home in Minford
4.95 out of 5 average rating, 268 reviews

Creekside Haven Tiny Home Spring Dates Open!

Welcome to Creekside Haven! Tucked along a peaceful creek in Minford, OH, our cozy tiny home is the perfect getaway for couples, families, or traveling professionals looking for comfort and convenience. Relax by the fire pit, swing in the hammock, or unwind inside with all the comforts of home! Pets are welcome with prior approval. Please note we can only allow small dogs (under 30 pounds).

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, 293 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 $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,530 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

    50 properties have a dedicated workspace

  • Wifi availability

    90 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