Vacation rentals in Ashland

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Top-rated vacation rentals in Ashland

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

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Top guest favorite
Home in Russell
4.98 out of 5 average rating, 400 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.

Guest favorite
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, 366 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 favorite
Cabin in McDermott
4.86 out of 5 average rating, 505 reviews

Cabin bordering Tremper Mound Preserve

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 favorite
A cozy living room features two brown leather sofas and a wooden coffee table at the center. A flat-screen TV is mounted on the wall, while a lamp with an intricate shade provides ambient lighting. A textured area rug lays underneath, adding warmth to the space.
Home in Ashland
5 out of 5 average rating, 23 reviews

The Bunkhouse • South Ashland Retreat • Near KDMC

Welcome to The Bunkhouse! Located in a quiet, South Ashland neighborhood just minutes from shopping, dining, and all of the amenities of downtown Ashland. Featuring two fully furnished bedrooms, each with ample clothing storage and mounted 32” Roku TVs. Relax in the living room with a 55” smart TV and enjoy a fully stocked eat-in kitchen complete with a coffee maker for your morning routine. Add our adjoining listing "The Paddock" to host groups of up to 8! Extended stays always welcome!

Top guest favorite
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, 162 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 favorite
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, 176 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 favorite
Tiny home in Minford
4.95 out of 5 average rating, 269 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).

Top guest favorite
The brick exterior of the building is complemented by warm brown awnings above the entrance. Neat landscaping with shrubs and grass borders the structure, while nearby sidewalks provide access to the first floor entrance.
Apartment in Huntington
4.92 out of 5 average rating, 169 reviews

Cozy and Quiet 1 bedroom unit near Ritter Park

This well maintained property is conveniently located just a short walk from Ritter Park and very close to downtown. This clean one bedroom apartment is neatly decorated with western decor and offers a full kitchen, full size bed, living and dining room. The unit is located on the first floor with private entry and laundry available in the building.

Guest favorite
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, 294 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.

Top guest favorite
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, 340 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.

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, 401 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 vacation 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 vacation rentals in Ashland

  • Total vacation rentals

    Explore 90 vacation rentals in Ashland

  • Nightly prices starting at

    Ashland vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 4,530 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Ashland vacation rentals include wi-fi 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!

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