Holiday houses in Ashland

Upscale Loft w/hot tub in Private Wooded Setting

Situated just minutes from Mohican, Malabar, and Snowtrails (not far from I-71 or mid-ohio) this is the perfect couples getaway. Settle in to a serene stay with everything you need for a memorable retreat. Hot tub, walk in couples rain shower, kitchenette, cozy fireplace, out door propane fire ring, and luxurious bedding accommodations all nestled in a beautiful wooded landscape. Host is available just off the main driveway. Makes the perfect retreat for couples needing a romantic get-a-way.

Family · Location · Outdoor spaces

Hummingbird Guest Loft

Quaint Guest Loft in the town of Ashland. In the heart of town, within minutes of walking to Ashland University. University is a 5 minute walk. One block from Freer Field with walking paths and where the Ashland Hot Air Balloon Fest is held every July 4th. Short drive to Mochican State Park. Take a hike, mountain bike, ride horses on the many bridle trails, canoe, fish and picnic. Explore the many restaurants, golf courses and farmers market. We will be there for you as often as needed.

Value · Family · Kitchen

The Uptique Loft

Welcome to The Uptique Loft managed by Steve and Miranda. Our stylish loft space is located in the heart of downtown, just steps away from the city's best restaurants, shops, and attractions. Enjoy a spacious layout with modern amenities, including a fully equipped kitchen, sizable living area, and cozy bedroom. Take in the city views right from the dining room table through the large bay window. Perfect for a weekend getaway or extended stay, The Uptique Loft is your ideal urban retreat.

Location · Value · Getting around

Whispering Pines Retreat by Private lake/ Villa #2

Whispering Pines Retreat #2 Kick back and relax in this calm, stylish space. Only 1/2 mile off SR 30, Overlooking a large pond with a swim area and beach. A massive 2 person shower and a hot tub are only a few things you will love about this retreat. This listing is for Villa and lake #2 and is what you are seeing in the photos. There is another Villa and Lake #1 on the same property. If you want to book both on the same days you can do so by going to my profile and finding #1 there.

Family · Value · Walkability

The South House-no extra fees from Host

This 120 year old farmhouse in the middle of town is a great accommodation for visiting the university, our awesome downtown, or our great local parks. 1st floor is primarily office space for my local small business, while 2nd floor hosts 2 bedrooms & bathroom, & 3rd floor living area. Centrally located, Unique & cozy, nearby highway, food, hiking, university, & hospital. Clean & charismatic! Homeowner or staff sometimes present M-F, 9-2 on first floor. No indoor smoking

Location · Value · Walkability

Perfectly Petite!

This one-of-a-kind, stylish studio home located in Ashland Ohio is a real treat! A modern eat-in kitchen with granite countertops, custom Amish made cabinetry, recessed and pendant lighting. A pristine, up-dated bathroom with a walk-in shower. A full-sized, stacked washer and dryer. The cozy living area has a queen size bed, a love seat, a larger, smart TV. The aesthetics of this home are simple, yet chic! The space is perfect for one night or an extended stay.

Value · Location · Wi-Fi

Charming Century House

Located one block from Ashland University, and Freer Field, home to the Ashland Balloon Fest, as well as a 2 min drive from downtown, this private house is comfortably furnished with everything you may need for a relaxing stay. This newly renovated home has a full kitchen with all new appliances, two bedrooms, one full bath, and a spacious common area. Centrally located it is close to a variety of interests, this home is perfect for couples or groups of five!

Value · Location · Hospitality

Spacious Mid-Mod Getaway w/ Nature Views!

So much to enjoy under one roof! Get ready for an unforgettable stay. -Pool & poker tables, record player, piano, custom bar -Spacious, unique midcentury home in a cute, quiet, & safe neighborhood -2 cruiser bikes, fire pit, hammock chair, gas grill & view of nature and wildlife -Backyard paths to woods, streams, & biking/walking trails -Golf course across the street. -Walk or drive 5 min to restaurants, groceries, + quaint downtown Extended stays welcome!

Value · Location · Accuracy

Mohicanville Hideaway

Enjoy a tranquil getaway at this cozy and historic 1836 log home in the woods. During your stay, you will be greeted with a tasteful mix of antique features, Amish craftsmanship, and comfort. Start your day with a cup of coffee or tea on the screened porch in the company of the deer who often visit. End your day relaxing in the hot tub or unwinding next to a wood-burning fire (inside or out) before luxuriating in bamboo sheets for a restful night's sleep.

Family · Location · Comfort

Downtown unique 4 bedroom Little Red Hen

The Little Red Hen Inn is a charming and expansive top-floor retreat in one of Ashland’s historic buildings. This cozy four-bedroom, two-bath Airbnb showcases unique, original artwork and locally crafted wheel-thrown pottery, creating a vibrant inviting atmosphere. Perfect for relaxing or entertaining, the space offers ample room to unwind with friends and family. ** NO BALCONY CURRENTLY. Under construction. Sleeping arrangements are still the same !!

Location · Family · Skiing

Deluxe Office Guest House

Elegance meets quiet living and plush comfort in this inviting modern office. Our Deluxe Office Guest House is the perfect overnight stay for on-the-go working singles or couples. Featuring a full kitchen, bath, washer & dryer, two work spaces, wi-fi, and TV with electric fireplace and queen size bed.

Value · Family · Condition

Charles Mill Lake Quonset Hut • Fire Ring & Kayaks

Experience a stay unlike any other in this restored WWII Quonset Hut—nestled in a quiet lakeside community near Charles Mill Lake. Perfect for outdoor lovers, it offers quick access to public hunting grounds, kayak adventures, and nearby parks like Mohican State Park, Malabar Farm and Snow Trails.

Family · Location · TV