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
A welcoming entrance is framed by a charming wooden fence and lush greenery. A path of stone pavers leads to a white door, flanked by vibrant plants and flowers. Sunlight filters through the trees, creating a serene outdoor atmosphere.
Loft in Ashland
4.99 out of 5 average rating, 228 reviews

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.

Top guest favorite
The exterior of the Quonset Hut is showcased, featuring an arched design with blue siding. Two kayaks, one red and one yellow, are secured against the wall. A stone pathway leads up to a set of steps, surrounded by lush greenery and trees.
Hut in Ashland
5 out of 5 average rating, 167 reviews

Quonset Hut | Charles Mill Lake | Mohican | AU

Experience a unique stay in a WWII military Quonset Hut, turned a beautiful home nestled within a serene lakeside community. For nature enthusiasts, this property is a dream come true. Situated in an optimal location, it offers access to hundreds of acres of public hunting grounds and near picturesque Charles Mill Lake, perfect for fishing and outdoor adventures. Mohican State Park, Snow Trails, Malabar Farm State Park, Shawshank Trail, Mid-Ohio Sports Car Course, Ashland University nearby.

Top guest favorite
A cozy living area features a light gray sofa and a colorful lamp, creating a relaxed ambiance. The wood flooring connects to an open kitchen area with a bar and high stools, while a vibrant bean bag chair adds a playful touch.
Apartment in Ashland
4.99 out of 5 average rating, 106 reviews

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 !!

Guest favorite
A cozy sleeping area features a spacious bed with a textured blanket and decorative headboard. Two accent chairs sit beside a small side table, complemented by warm lighting from bedside lamps. Soft rugs cover the floor, adding to the welcoming atmosphere.
Apartment in Wooster
4.84 out of 5 average rating, 298 reviews

Cozy Abode

The space is a dedicated basement apartment. The space has its own door and lock, but guests will enter through a shared garage entrance. The decor is neat and modern. There is a small kitchenette, giving guests the ability to eat in, or make coffee. The cozy sitting area is a great place to wind down for the evening or enjoy a morning cup of coffee. The apartment is below our living space. While we will do our best to keep noise to a minimum, you will hear kids/footsteps during the day.

Top guest favorite
A vibrant pink bicycle serves as a decorative centerpiece in a garden filled with lush green plants. The bike is surrounded by small lights, and a classic red lighthouse ornament adds a charming touch to the landscape. The entrance pathway leads to the house, framed by greenery.
Guesthouse in Glenmont
4.94 out of 5 average rating, 281 reviews

Glenmont Bike&Hike Hostel

This Airbnb was created for bikers riding on the OTET. This is above a detached garage at zip code 44628. This one open room with a private bathroom includes towels (toilet, shower, and sink). There is a double bed with linens, tv, wifi, mini-kitchen with microwave, sink, and refrigerator. The stove is not working now. The Airbnb is located a few minutes from the OTET/Glenmont Trailhead. Note: NO PETS or children under age 12 allowed. No smoking or vaping allowed in Airbnb.

Guest favorite
Home in Ashland
4.84 out of 5 average rating, 142 reviews

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

Top guest favorite
A vibrant collage presents various areas of the midcentury home. Features include a spacious kitchen with modern appliances, an inviting dining area, a stylish green pool table, and a cozy outdoor seating arrangement. The branding logo 'The Rambler' is prominently displayed.
Home in Ashland
5 out of 5 average rating, 107 reviews

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!

Top guest favorite
The red brick exterior of a historic building is highlighted by large arched windows and a prominent entrance door. A copper-colored metal roof adds character, while surrounding greenery and decorative landscaping enhance the setting. A staircase leads to the upper level, providing additional access.
Apartment in Mansfield
4.97 out of 5 average rating, 258 reviews

The Carriage House- "Coachman's Inn unit"

160 Year old Historic Landmark, Centrally located in downtown Mansfield! Just a couple minute drive to Prohibition at the Caverns or about a 15 minute walk to the Carousel District! Originally built as a Carriage Barn for the Bissman Family circa 1860 ...Only 3.2 Miles from the Reformatory, 9.7 Miles from Mid Ohio Race Track, 1 Mile from Kingwood Center & only 7.3 Miles from Snow Trails Ski Resort! Rest assured we take cleaning very serious!

Top guest favorite
A four-poster queen bed is centered in the room, complemented by plush bedding and decorative pillows. Soft lighting is provided by bedside lamps on either side. An artwork hangs above the bed, and light-colored curtains frame a window, enhancing the calming atmosphere.
Apartment in Wooster
4.99 out of 5 average rating, 197 reviews

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.*

Top guest favorite
A comfortable sofa is adorned with two decorative pillows and a patterned throw blanket. A small side table holds a tissue box and remote control. Soft lighting from a nearby lamp creates a cozy ambiance, and a wall art piece featuring llamas adds a unique touch.
Apartment in Wooster
4.95 out of 5 average rating, 196 reviews

Private, spacious 1 bedroom apt near Amish Country

Enjoy a private 1 bed, 1 bath, full kitchen, private patio, close to downtown Wooster, 1.5 mi from OARDC/Secrest Arboretum, 3.5 mi to College of Wooster, 1 hr drive to CLE airport. Enjoy the heart of Amish Country while saving money being 30 min away from the tourist hub! Family lives on-site (above the airbnb) so some dog and kid noise expected. Plenty of parking for 2 cars. Apt is self-check in.

Top guest favorite
A modern kitchen features dark cabinetry and stainless steel appliances, including a refrigerator and stove. A countertop island with three stools provides seating. Natural light streams through a window above the sink, highlighting the organized countertop with various kitchen items.
Guest suite in Ashland
4.99 out of 5 average rating, 754 reviews

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.

Top guest favorite
The main house, showcasing Greek revival architecture, is complemented by a new guest house attached to the garage. A spacious lawn is adorned with a circular stone flower bed and a fountain, under a vibrant sky dotted with clouds.
Guest suite in Ashland
5 out of 5 average rating, 345 reviews

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.

Popular amenities for Ashland vacation rentals

When is the best time to visit Ashland?

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Ashland?

    Yes! Work meets play with ease at over 10 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Ashland?

    Four-legged friends are welcome in Ashland. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Do house rentals in Ashland have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Ashland?

    Ashland has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Ashland?

    Experience the best of Ashland with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Ashland have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Ashland

  • Total vacation rentals

    Explore 30 vacation rentals in Ashland

  • Nightly prices starting at

    Ashland vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 1,500 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Ashland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Ashland rentals

  • 4.8 Average rating

    Ashland stays are highly rated by guests—averaging 4.8 out of 5!

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