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.

Clever Oasis Near Mid-Ohio Race Track & SnowTrails

You will be staying in a relaxing, freshly renovated basement apartment with air fryer, hotplate, microwave, toaster, coffee maker & private entrance. Our space is family and business friendly conveniently located just 5 miles from Interstate 71, 10 miles to Mid Ohio Race Track, Snow Trails, Malabar farm, & MANSFIELD Reformatory. Onsite parking and motorcycle friendly with covered parking for motorcycles only. Our home sleeps up to 3 guests with a queen bed and futon. Hot tub available!

The Carriage House- " Stables Unit "

Located in Downtown! Only a couple minute drive or 15 minute walk to the Carousel! 7 Miles from Snow Trails, 3.2 Miles from the Reformatory, 9.7 Miles from Mid Ohio Race Track, 1 Mile from Kingwood Center, Many downtown restaurants ! Coffee shops! Including Antique and Specialty shops. Fully Equipped kitchen w/Full size Refrigerator, Stove/ oven, Keurig Coffee maker and microwave . Cooking & Dinning essentials provided. Door Code will be sent out the day of arrival before check in time !

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 and inviting atmosphere. Perfect for relaxing or entertaining, the space offers ample room to unwind with friends and family. After a day of exploring, return to this artistic haven for a relaxing and memorable stay. Located Down town Ashland !!

Whispering Pines Retreat by Private Lake/ Villa #1

Whispering Pines Retreat #1 This stylish villa is Located 1/2 mile from 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 of the things you will love about this Retreat. This listing is for Villa and lake #1 and is what you are seeing in the photos. There is another Villa and Lake #2 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 the other listing there.

The South House-no extra fees from Host

This century 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 biz, 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

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!

Historic Downtown Wooster Victorian Apartment #2

Step back in time to the 1800s in this charming brick Pioneer House in Historic Downtown Wooster. Enjoy the entire first-floor apartment (approx. 1500 sqft), blending vintage elegance with modern comfort. All while being just a block from local eateries, boutique shopping, and historic sites. *Please note there's construction taking place across the street during daytime hours, which may result in some construction noise during your stay.*

Unique Home in Holmesville/ Holmes County

●20 minutes from Wooster, Millersburg, Berlin, Loudenville, and Mt Hope, and within a short drive to Mohican State Park. ●Firepit and chairs on the back patio ●Built in 2022 with contemporary styling and unique touches throughout. ●Set in the small town of Holmesville with a pizza shop and Blue Moon Bistro close by. ●Quality whole bean coffee provided

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.