Holiday rentals in Wooster

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Top-rated holiday rentals in Wooster

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Top guest favourite
A cozy living area features a brown leather sofa and a light-colored armchair, positioned near a side table with a floral arrangement. A patterned wall adds color, and soft lighting is provided by two table lamps. Green drapes frame the windows.
Home in Wooster
4.97 out of 5 average rating, 103 reviews

TheLegacyHouse: Historical Suite Close to Downtown

Welcome to The Legacy House Wooster! This is a charming Victorian home within two blocks from the wonderful downtown attractions, shops and upscale dining. Our grandparents' love for people and hospitality inspired us to create a warm and inviting home where we could share their legacy and traditions with others while restoring their historic home back to it's former beauty. Experience all the amazing opportunities Wooster has to offer while enjoying a unique, comfortable home to relax in!

Guest favourite
A living room featuring a dark leather sofa with several decorative cushions, accompanied by a matching armchair. A coffee table rests on a patterned rug, and a television is positioned on a modern stand. The space is illuminated by natural light filtering through floral-patterned window curtains.
Flat in Wooster
4.95 out of 5 average rating, 242 reviews

Your 2nd Home Away From Home l Prime location

This is a fully furnished apartment that has all the amenities of home. It is an updated apartment in an older home, but thoughtful touches and attention have been taken to make this feel very comfortable and relaxing. You'll be pleasantly surprised with the atmosphere and the space that you'll have while staying here. The apartment is conveniently located within a couple short blocks of the college, and just a short distance to the wonderful downtown Wooster with plenty of shops and dining.

Guest favourite
A secluded Safari tent is situated among trees, illuminated by string lights. A gravel area features several dark wooden Adirondack chairs arranged around a fire pit, inviting relaxation in the serene outdoor setting.
Place to stay in Wooster
4.98 out of 5 average rating, 132 reviews

Luxury Creekside Safari Tent w/ King Bed *Hot Tub*

Escape to a secluded luxury Safari tent situated on 60 wooded acres that overlooks Little Killbuck Creek. Enjoy hiking trails & a natural waterfall a short hike upstream. The tent is built on a platform deck with canvas sides, metal roof, high end luxury flooring, luxurious King size bed, full kitchen, dining, A/C, ceiling fans & heaters. The large separate bath house boasts a rainfall shower and bluetooth speakers. Enjoy a hot tub that overlooks the creek & front porch for bird watching.

Guest favourite
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.
Flat in Wooster
4.84 out of 5 average rating, 303 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 favourite
A charming front porch is adorned with climbing greenery and seasonal flowers, creating a welcoming exterior. An American flag is displayed, adding a touch of tradition. The house features light-colored siding and a green roof, complementing the natural surroundings.
Home in Wooster
4.97 out of 5 average rating, 200 reviews

Meg's Lucky Buckeye

We have revived the unique character of this old house, built in 1864. The floors aren't level - some of them creak - but the details are lovely, and generous light fills the rooms. In keeping with our other rentals -- we are pet friendly. Our daughter is a College of Wooster alum and that's what brought us to Ohio - she stayed. I named the house in memory of my mother, who never set foot in Ohio but always believed buckeyes are lucky. We feel lucky to have found it; hope you do too.

Top guest favourite
A cozy seating area is visible through a set of double doors, featuring two armchairs with light-colored cushions. A small table with a lamp stands between the chairs, and large windows overlook a green outdoor space, allowing natural light to fill the room.
Home in Wooster
4.96 out of 5 average rating, 197 reviews

Bonnie Jane House

The Bonnie Jane House is a family friendly space on a quiet, tree-lined street, within sight of the College of Wooster and minutes from downtown. Perfect for college, business, and local tourism. The space includes 3 bedrooms (sleeps up to six) and 2.5 bathrooms stocked with towels, linens, and basic toiletries. With the full couch and inflatable mattress available, plus plenty of floor spaces, we can accommodate as many as 8 guests. There is an upstairs apartment on the 3rd floor.

Top guest favourite
The exterior of Apple Blossom Cottage is showcased with a modern white facade and a distinctive metal roof. A welcoming porch features rocking chairs and a scenic view of the rolling hills in the background. The landscape includes well-maintained greenery and a gravel pathway.
Cottage in Millersburg
4.99 out of 5 average rating, 244 reviews

Apple Blossom by Olde Orchard Cottages

Welcome to Apple Blossom Cottage... We invite you to be our guest! For years Mary + John, the founders of White Cottage Company, dreamed of creating a space for people to retreat to that would be so cozy, peaceful, and relaxing that guests wouldn't want to leave! Their dream is now a reality with the completion of Olde Orchard Cottages Apple Blossom + Sparrow's Nest - nestled within the serene rolling hills in the heart of beautiful Amish Country.

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
4.99 out of 5 average rating, 368 reviews

Downtown Brick Loft Above The Exchange Coffee Co

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.

Guest favourite
A modern living area features a comfortable brown leather sofa paired with an accent chair beside a sleek, wooden coffee table. A mounted television is above an electric fireplace, providing a cozy focal point. Natural light filters through dual windows adorned with light curtains.
Loft in Wooster
4.88 out of 5 average rating, 142 reviews

Lovely 2-bedroom loft with indoor fireplace

Welcome! This spacious 2 bedroom 1 bath apartment is located in the heart of Downtown Wooster. Walking distance from restaurants, coffee shops, boutique shopping, minutes from the College of Wooster, a short drive to Amish country and much more! This unique and stylish space will have everything you need for your stay. Whether you are looking for a night away or wanting to stay long term Life on Liberty was designed with you in mind.

Top guest favourite
The open living area features warm wood flooring and exposed brick walls. A spacious seating arrangement includes a dark leather sofa and a tufted coffee table. The kitchen boasts white cabinetry, stainless steel appliances, and a breakfast bar with two stools. Natural light filters through the window.
Loft in Wooster
4.98 out of 5 average rating, 154 reviews

Historic hideaway in downtown studio apartment

This urban-styled studio is located in the heart of historic downtown Wooster. You can walk to some of the most popular local restaurants, specialty boutiques, coffee shops, and more. Featuring the original exposed brick, this unique space can accommodate 1-2 guests with one king bed, living area, and fully stocked kitchen. Explore the rooftop access where you can sit and enjoy the scenic views of downtown.

Top guest favourite
Cabin in Strasburg
4.98 out of 5 average rating, 364 reviews

Scandi Cabin•Hot Tub• 4 Electric Fireplaces•

The White Oak Cabin: Built in ‘22 •2 bed •2 bath •Hot Tub •Fully stocked kitchen •4 Electric Fireplaces •Living room - 50”TV •Climate control in each room •Step ladder to loft In the loft: •Workspace •1 Huge Sectional-room for 2 to sleep •50” TV •Fireplace 30 minutes > Pro Football Hall of Fame 15 minutes > Sugarcreek (Amish Country) 20 minutes > 6 wineries 60min > Cuyahoga Valley National Park

Top guest favourite
Flat in Wooster
4.95 out of 5 average rating, 205 reviews

Wooster private apartment 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.

Popular amenities for Wooster holiday rentals

When is the best time to visit Wooster?

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Frequently Asked Questions

  • What are the best places to stay in Wooster?

    Many visitors look for places to stay near downtown Wooster, which has walkable access to shops, restaurants, and the arts district. Quiet residential neighborhoods also provide options with larger homes and green spaces.

  • What are the best things to do in Wooster with kids?

    Kids can enjoy the playgrounds, nature trails, and family-friendly exhibits at Secrest Arboretum. Seasonal events, hands-on museums, and family cooking classes are also popular choices for visitors with children.

  • What are some of the best things to do in Wooster?

    Explore the shops and restaurants in historic downtown Wooster, visit Secrest Arboretum for its gardens, or learn about the area's history at the Wayne County Historical Society. Art galleries and local theaters often have changing exhibits and performances.

  • How is the weather in Wooster?

    Wooster experiences cold winters with highs around 20–36°F (-7–2°C) and warm, often humid summers that reach about 80–84°F (27–29°C). Rain falls throughout the year, so packing an umbrella or rain jacket is useful.

  • When is the best time to visit Wooster?

    Late spring through early fall is often recommended for milder weather, green landscapes, and frequent community festivals. Fall brings colorful foliage and seasonal farm markets to the area.

  • What are the best places to visit in Wooster?

    Explore charming downtown streets, stroll through Secrest Arboretum, or learn at campus museums at The College of Wooster. The Wayne County Historical Society is also often recommended for insights into local history.

  • What are some hiking trails in Wooster?

    Wooster has scenic trails at parks and nature preserves, including paths through forests, meadows, and wetlands. Secrest Arboretum is frequently suggested for relaxing strolls and educational displays.

  • What are some family activities we can do in Wooster?

    Families can explore playgrounds, interactive museums, or the local nature center in Wooster. Seasonal festivals and art workshops are also commonly enjoyed by travelers with children.

  • What are some of the best day trip ideas from Wooster?

    Visitors often plan day trips to explore Amish Country, local wineries, or state parks known for hiking and wildlife. Art enthusiasts might enjoy museums or architectural sites in nearby towns.

  • Are there any pet friendly accommodations available in Wooster?

    Wooster has a variety of pet friendly accommodations, including vacation rentals with fenced yards or easy access to walking trails and parks. Some stays provide amenities like pet bowls or welcome treats.

  • What are some local tips for visiting Wooster?

    Locals often recommend checking community calendars for pop-up events and visiting the public market for regional produce. Exploring on foot can provide easy access to downtown shops and cultural sites.

  • What is Wooster known for?

    Wooster is known for its agricultural heritage, vibrant local arts, and the presence of The College of Wooster. The city also attracts visitors with its historic downtown and seasonal community events.

  • What are the best hidden gems to explore in Wooster?

    Wooster has art galleries, vintage shops, and botanical gardens that are frequently suggested by locals. Quiet neighborhoods with historic architecture and unique sculptures also invite exploration.

  • What are the best foods to try in Wooster?

    Wooster is known for regional farm-to-table dishes, local ice creams, and specialties such as Amish-style baked goods and cheeses. Many visitors also seek out craft beer or classic comfort foods in the area.

  • What should I bring for a trip to Wooster?

    Prepare for changing weather by packing layers, a light rain jacket, and comfortable walking shoes. Bringing a reusable water bottle and a small backpack is useful for exploring local markets or parks.

  • What is the nightlife in Wooster like?

    Wooster's nightlife is centered around locally owned restaurants, craft breweries, and live music spots. Visitors can explore casual pubs, neighborhood bars, or occasional performances at historic venues.

  • What are the most popular events or festivals in Wooster?

    Wooster hosts community fairs, seasonal festivals, and events celebrating food, music, and local arts. The Wayne County Fair and Woosterfest are often recommended for their lively atmosphere, regional food, and family activities.

  • Are there family friendly vacation rentals in Wooster?

    Wooster has many family friendly vacation rentals, including homes with extra bedrooms, kitchens, and outdoor spaces. Look for stays near parks, community centers, or family-focused attractions to help create a welcoming environment for all ages.

Quick stats about holiday rentals in Wooster

  • Total holiday rentals

    Explore 70 holiday rentals in Wooster

  • Nightly prices starting at

    Wooster holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 5,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 of Wooster holiday rentals include wifi access

  • Popular amenities for guests

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

  • 4.9 Average rating

    Wooster stays are highly rated by guests – averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. Ohio
  4. Wayne County
  5. Wooster