Vacation rentals in Ashland

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.

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.

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

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!

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!

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 !!

Overton Valley: Secluded Cabin on 10 acres

Slip away to a secluded cabin in the woods on 10 acres for a peaceful getaway. The abundance of wildlife and nature's beauty is sure to leave you feeling relaxed and restored. Conveniently located close to Wooster, Ashland, Akron, Canton, and Cleveland. Explore Amish country, visit Cedar Point with the kids, take in a local winery, check out The Pro Football Hall of Fame, or go for a hike on the property. The local attractions are endless!

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.

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.

Sycamore Hill Farm

Our historic family farm has 180 acres. The main house has been renovated to reflect a Greek revival kind of architecture that was prevalent in this area during the early 1800’s. The guest house is of new construction and is attached to the garage. It has a private porch attached to the back.

Cozy Ashland Cottage - Close to Downtown

Welcome to our cozy Ashland cottage! The home is located just 3 minutes from downtown, 4 minutes to Ashland University, and just over 10 minutes to I71. The home is fully stocked with all of the essentials you will need for a great stay in our little town!

The Acacia

A luxurious A-frame retreat with spacious modern timber frame and soaring ceilings, this thoughtfully-designed getaway has been curated for your comfort. Your escape to the Acacia promises a harmonious blend of modern luxury and timeless tranquility.