Vacation rentals in Sullivan

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Top-rated vacation rentals in Sullivan

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Top guest favourite
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.

Guest favourite
A single-story house is visible, featuring a gray exterior and a black roof. Two small windows are positioned symmetrically on either side of the front door. A well-maintained lawn stretches in front, and tall trees are present in the background, adding to the natural setting.
Home in Wellington
4.89 out of 5 average rating, 159 reviews

Private Rochester Home

A two bedroom house in the small village ( less than 200 residents) of Rochester, OH. There are woods and open areas of about 4.0 acres with availability of fire pit for a peaceful evening. Property has a steam engine to view. Playground about one quarter mile from house. We are still updating home and property. Private, quiet area except but there is train track about 300 feet from the house. You are 20 minutes from Ashland, OH and Oberlin, OH. 45 minutes from Cedar Point and Cleveland.

Top guest favourite
A historic Victorian house is showcased with a prominent front porch and detailed architectural elements. Surrounded by well-maintained greenery, the two-story structure features large windows that allow natural light. A paved walkway guides visitors from the street to the welcoming entrance.
Guest suite in Wellington
4.99 out of 5 average rating, 106 reviews

Baundale Homestead in Historic Wellington, OH

Our 1800's Victorian beauty does not hold back on charm. This country gem is perfect for those who need an escape from the hustle and bustle of the busy city. Located in historic Wellington, Ohio, The Baundale is only 8 miles from Oberlin College and 2.5 Miles from Findley State Park. Our stay offers numerous amenities such as free parking, a private entrance for guests and a very spacious living area. We are happy to answer any questions you might have. Thank you for viewing our listing!

Guest favourite
A modern villa sits beside a tranquil pond, with warm lights reflecting on the water's surface. The structure features large windows and a spacious patio with outdoor seating. Surrounding greenery enhances the serene environment, providing a peaceful backdrop.
Villa in Jeromesville
4.93 out of 5 average rating, 212 reviews

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.

Top guest favourite
A mid-century cottage is set within a lush garden, featuring a stone fireplace and a covered porch. The exterior showcases a blend of siding and a stone chimney, surrounded by blooming flowers and greenery, creating a peaceful outdoor setting.
Cottage in Amherst
4.98 out of 5 average rating, 268 reviews

The Farmer's Cottage

The Farmer's cottage is a cozy one bedroom mid-century farm cottage on 2 acres of land nestled among farm fields and woodlands . It features a queen-sized bed, bath and full custom kitchen along with a smart TV and Wi-Fi. . A park-like yard with a stone fireplace and solar installation awaits. This country property features self contained utilities including a water well, sanitation and electricity. Enjoy fresh eggs from our chickens and baked goods from our farm kitchens.

Top guest favourite
A well-maintained lawn surrounds the cabin, leading to a serene, spring-fed pond. Two trees provide shade for a hammock, creating a peaceful spot to relax. The greenery reflects the tranquil atmosphere of the property, inviting guests to enjoy the natural setting.
Cottage in Wooster
4.95 out of 5 average rating, 290 reviews

Cabin with pond & Fireplace * Hot Tub * King Bed

A quaint, cozy newly remodeled in 2025 cabin on 60 wooded acres perfect for a couples getaway. 8 minutes to a great downtown for shopping unique boutiques, dining, local wineries, breweries and distillery! Enjoy peace & tranquility in natures setting. Cozy up to a massive stone wood burning fireplace both inside and on the screened in porch. The brand new private hot tub boasts natural spring water and is just outside the door from the cabin and overlooks the natural spring ponds.

Top guest favourite
A serene bedroom features a queen size bed dressed in soft linens, accompanied by decorative pillows. Natural light filters through the wooden blinds on two windows. A small side table sits next to the bed, and a vintage cabinet is placed against the wall.
Apartment in Medina
4.92 out of 5 average rating, 318 reviews

Uptown Liberty I

Uptown Liberty I is a beautiful and unique apartment unit located directly on Medina Square. (Castle Noel is right next door!) This unit features a kitchenette, a full bath and a queen size bed and if you're looking for a bigger apartment and your own garage parking, deck, patio, grill and big back yard we have two more apartments at Liberty Manor within a few minutes walking distance to the historical Uptown Medina Square just look up Liberty Manor ll & lll. it's a hidden Gem!

Top guest favourite
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 favourite
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, 200 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 favourite
An open-concept living area features exposed brick walls and high ceilings with dark beams. A large island sits in the kitchen, while comfortable seating is arranged nearby. Multiple windows provide natural light and a view of the surroundings, enhancing the spacious feel of the loft.
Loft in Canal Fulton
5 out of 5 average rating, 332 reviews

Brick Loft in Historic Downtown Canal Fulton

Located in the heart of historic downtown Canal Fulton, this charming brick loft will truly take you back in time. Walk or bike to all the local restaurants and shops around town or grab coffee at The Exchange downstairs. The 13 large windows give a panoramic water view of the canal way and downtown. Every detail in this space has been lovingly created with comfort and inspiration in mind. Relax and enjoy this one of a kind location.

Top guest favourite
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, 197 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 favourite
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.

Popular amenities for Sullivan vacation rentals

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