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Holiday rentals in Wooster

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Top-rated holiday rentals in Wooster

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Flat in Wooster

4.87 out of 5 average rating, 387 reviews

★★Penthouse Suite Downtown Wooster on the Square★★

Roughly 2200 square feet with all the comforts of home in Downtown Wooster. Luxurious suites with fully equipped kitchen, spacious bath & shower, Jacuzzi, office, wireless, washer/dryer and cozy living area with TV all within walking distance of restaurants, shopping, and coffee shops of downtown Wooster. This unit will give you more bang for your buck than a hotel without the worry of having to drive after a drink or two from the 20 plus restaurants and pubs of downtown within walking distance.

4–11 Oct

$245 SGD per night

Guest favourite

Flat in Wooster

4.99 out of 5 average rating, 182 reviews

Orchard Lane Getaway

We are waiting for you! We offer a quiet, rural setting in a 2 bedroom apartment with full amenities, separate from our home. Each room is decorated in its own unique style. You have internet access, TV and are close to all major shopping and places to eat. We request that guests be non smokers, no pets and one adult 21 or over. We are fully vaccinated, in our 70's and we ask our guests to follow all current COVID guidelines. $10.00 extra per guest per night over 5 guests with prior approval.

14–21 Mar

$98 SGD per night

Guest favourite

Flat in Wooster

4.87 out of 5 average rating, 110 reviews

Very nice and clean two bedroom apartment on a quiet dead end street. This apartment is in the perfect location to get to anywhere you would like to go within the City in just a few miles!

Make this cozy, spacious apartment your home away from home. Centrally located between Downtown and Uptown Wooster. This home is with in walking distance of West View Manor and the Wooster Country Club. This convenient location gives you easy access to restaurants, shopping centers, the YMCA, the College of Wooster as well as Wooster High School all within 3 miles. It's perfect for one person or bring the whole family. Stop in for a visit and enjoy all the great city of Wooster has to offer!

18–25 Sep

$119 SGD per night

Guest favourite

Flat in Wooster

4.84 out of 5 average rating, 243 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.

26 Jul – 2 Aug

$90 SGD per night

Guest favourite

Home in Wooster

4.98 out of 5 average rating, 147 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.

5–12 Sep

$181 SGD per night

Guest favourite

Flat in Apple Creek

4.95 out of 5 average rating, 230 reviews

Summer Kitchen Retreat, Amish Country with sunsets

The Summer Kitchen is a country retreat apartment in the heart of Amish Country, Ohio. We are 5 minutes from Kidron, 25 minutes from Mt .Hope and Berlin tourist attractions. This private getaway for two adults comfortably offers a quiet country view of farmland and surrounding country living, atop a hill with beautiful sunsets. It's aptly named The Summer Kitchen because this structure was once used as the kitchen for all the summertime canning and cooking for farmstead living.

13–20 Mar

$145 SGD per night

Guest favourite

Flat in Wooster

4.9 out of 5 average rating, 115 reviews

Your Home Away From Home l Conveniently Located

Come stay at this cozy, peaceful and inviting home. This is a fully furnished apartment with two entrances, one of which is shared through a common area and one that is a private entrance. You are sure to feel at home with all of the amenities, such as a full kitchen, dining room, living room, etc. We have an onsite manager that will be available to answer any questions or concerns that you may have during your stay. We hope that you come and enjoy your stay and visit again.

11–18 Aug

$162 SGD per night

Guest favourite

Home in Wooster

4.94 out of 5 average rating, 141 reviews

Cozy Home near College of Wooster

Cozy 3 bedroom house near College of Wooster. Five minute walk to Timken Gymnasium or Freedlander Theater and a 10-15 minute walk to downtown restaurants, coffee shops and boutiques. Residential neighborhood near campus. All the amenities you will need for a comfortable and affordable stay. Relax in the living room, enjoy one of three queen size beds along with a fully equipped kitchen and dining area. Also feel free to park in our attached one car garage.

17–24 May

$194 SGD per night

Guest favourite

Guest house in Glenmont

4.91 out of 5 average rating, 152 reviews

Glenmont Bike&Hike Hostel

This Airbnb is located above the detached garage. It is one open room with a private bathroom that includes towels (toilet, shower, and sink). There is a double bed with linens, sofa, cots, 48-inch tv, mini-kitchen with microwave, stove, sink, and refrigerator. The Airbnb is located a few minutes from the OTET/Glenmont Trailhead. Note: NO PETS allowed. Please do not bring any children under the age of 12. No smoking or vaping allowed inside.

18–25 Sep

$70 SGD per night

Guest favourite

Townhouse in Orrville

4.95 out of 5 average rating, 102 reviews

Elegant Boho apartment in downtown Orrville

Retreat to the harbor. We created this space with you in mind. When we travel, we want Airbnb, a unique spot that allows us to relax and enjoy the moments. So when we bought this apartment, we knew from the start this place needed to be for guests, to give them a place of comfort and rest. So over the past few months, we renovated this place to have that "it" factor. Located right in downtown Orrville this is perfect for your stay/getaway.

12–19 Oct

$170 SGD per night

Guest favourite

Flat in Apple Creek

4.99 out of 5 average rating, 137 reviews

Esther's Amish Country Apartment

Esther's Amish Country Apartment is spacious (960 sq. ft. of living space) located on a beautiful quiet 2 acre property. It has a full kitchen, roomy living room area to relax, queen size bed and walk-in shower; additionally, Armstrong Cable with access Netflix, Prime, Apple TV and excellent WiFi for your entertainment We are an easy 15-20 drive to tourist attractions in the area. *** Read "Other things to note" below for details.

6–13 Jul

$139 SGD per night

Guest favourite

Loft in Wooster

4.99 out of 5 average rating, 140 reviews

Beautiful 2BR/2BA Loft Apartment Downtown Wooster

This 2500 sq ft stylish loft apartment is perfect for an entire family or large groups in beautiful Downtown Wooster. The apartment features a rooftop deck with spectacular views of Wooster and surrounding area, the primary bedroom has an en suite bath and walk-in closet, gourmet kitchen, large open dining and living areas, and on-site parking. Restaurants/bars, library, shopping, and parks are steps away.

12–19 Apr

$330 SGD per night

Holiday rentals for every style

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Popular amenities for Wooster holiday rentals

Free parking on premises

Air conditioning

Stay near Wooster's top sights

Ramseyer Farms9 locals recommend

Coccia House8 locals recommend

Buehler's Fresh Foods Wooster Milltown5 locals recommend

Muddy's5 locals recommend

Olde Jaol Steakhouse and Tavern8 locals recommend

Hartzler Family Dairy5 locals recommend

Other great holiday rentals in Wooster

Guest favourite

Home in Dalton

4.95 out of 5 average rating, 110 reviews

The Blacksmith House of Kidron

14–21 Feb

$200 SGD per night

Guest favourite

Guest house in Millersburg

4.99 out of 5 average rating, 110 reviews

New! Modern and cozy flat!

18–25 Jan

$146 SGD per night

Guest favourite

Holiday home in Smithville

4.87 out of 5 average rating, 115 reviews

Peaceful 2-BR Apartment in the Heart of Smithville

1–8 Dec

$149 SGD per night

Guest favourite

Flat in Dundee

4.99 out of 5 average rating, 346 reviews

Hidden Meadow's Apartment in a Quiet Setting

9–16 Nov

$166 SGD per night

Guest favourite

Place to stay in Millersburg

4.96 out of 5 average rating, 205 reviews

Thicket Cottage

17–24 Jul

$170 SGD per night

Guest favourite

Flat in Wadsworth

4.92 out of 5 average rating, 166 reviews

Cozy, Private Apt, 500ft from Wadsworth Square

30 Oct – 6 Nov

$98 SGD per night

Guest favourite

Guest house in Ashland

4.98 out of 5 average rating, 595 reviews

Guest Home minutes from Ashland University

25 Feb – 4 Mar

$98 SGD per night

Guest favourite

Flat in Wooster

5.0 out of 5 average rating, 29 reviews

Historic Downtown Wooster Victorian Apartment

5–12 Oct

$128 SGD per night

Quick stats about holiday rentals in Wooster

Total rentals
60 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
3.9K reviews
Nightly prices starting at
$14 SGD before taxes and fees

Destinations to explore