Holiday rentals in Wooster

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Top-rated holiday rentals in Wooster

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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.

23–30 Oct

$96 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!

11–18 Sep

$115 SGD per night

Guest favourite

Flat in Wooster

4.95 out of 5 average rating, 209 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.

26 Sep – 3 Oct

$166 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.

18–25 Mar

$177 SGD per night

Guest favourite

Holiday home in Smithville

4.87 out of 5 average rating, 114 reviews

Peaceful 2-BR Apartment in the Heart of Smithville

Quiet 2-BR apartment located on the first floor in the heart of Smithville, Ohio. About a 10 min drive to Wooster. The apartment sits in front of a park which has access to hiking paths, baseball, and soccer fields. His and Hers bicycles will be provided for use free of charge during the summer. Local restaurants and stores are walking distance. Space includes 2 Queen Beds Amenities include Wifi, Free parking for 1 vehicle, Washer/Dryer, Full Kitchen, Covered Front Porch and many more.

15–22 Aug

$163 SGD per night

Guest favourite

Loft in Wooster

4.97 out of 5 average rating, 166 reviews

Downtown Wooster Loft

Newly updated loft apartment in the heart of Downtown Wooster. This apartment is on the third floor of a beautifully renovated historic building housing several apartments, Flex Yoga Wooster on the second floor and Sure House Coffee and Meatheads Union on the first floor. We are within a few minutes walking distance to Restaurants, Bars, Boutiques, and Coffee Shops. New furniture, flat screen TVs, and updated flooring in 2022. Free Yoga, Fitness, and Aerial Classes with every stay.

23–30 Apr

$251 SGD per night

Superhost

Flat in Wooster

4.82 out of 5 average rating, 210 reviews

★★Boutique Downtown Lofted Flat on the Square ★★

Roughly 1,100 square feet with all the comforts of home in Downtown Wooster. Luxurious suites with fully equipped kitchen, spacious bath & shower, Jacuzzi, office, wireless, and cozy living area with flat-screen T.V. all within walking distance of restaurants, shopping, and coffee shops. 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.

23–30 Apr

$191 SGD per night

Guest favourite

Flat in Apple Creek

4.95 out of 5 average rating, 229 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.

4–11 Feb

$142 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 appartment with a private entrance through the garage. The decor is neat and modern. The space includes a small kitchenette, giving guests the ability to eat in, or make coffee before getting out and about. The cozy sitting area is a great place to wind down for the evening or enjoy a morning cup of coffee. The appartment is attached to our living space. While we will do our best to keep noise to a minimum, you will hear our two kids.

9–16 Jul

$86 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.

3–10 Nov

$190 SGD per night

Guest favourite

Townhouse in Orrville

4.95 out of 5 average rating, 100 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.

16–23 Feb

$159 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

$135 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Wooster holiday rentals

Kitchen

Wifi

Pool

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

Guest house in Glenmont

4.91 out of 5 average rating, 146 reviews

Glenmont Bike&Hike Hostel

24–31 Oct

$68 SGD per night

Guest favourite

Loft in Wooster

4.99 out of 5 average rating, 108 reviews

Stunning 2 BR, 2 BA, w/Elevator, Downtown Wooster

4–11 Feb

$325 SGD per night

Guest favourite

Cabin in Beach City

4.99 out of 5 average rating, 337 reviews

The A-frame at Creekside Dwellings [Hot tub]

30 Mar – 6 Apr

$210 SGD per night

Guest favourite

Home in Dalton

4.94 out of 5 average rating, 108 reviews

The Blacksmith House of Kidron

14–21 Mar

$196 SGD per night

Guest favourite

Guest house in Millersburg

4.99 out of 5 average rating, 109 reviews

New! Modern and cozy flat!

13–20 Mar

$143 SGD per night

Guest favourite

Guest house in Ashland

4.98 out of 5 average rating, 594 reviews

Guest Home minutes from Ashland University

27 Aug – 3 Sep

$96 SGD per night

Guest favourite

Flat in Wooster

5.0 out of 5 average rating, 25 reviews

Historic Downtown Wooster Victorian Apartment

21–28 Sep

$125 SGD per night

Guest favourite

Flat in Wooster

4.91 out of 5 average rating, 32 reviews

Quiet Country in the City, Main Floor

18–25 Dec

$121 SGD per night

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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

Holiday rentals in Wooster

Top-rated holiday rentals in Wooster

Flat in Wooster

Flat in Wooster

Flat in Wooster

Home in Wooster

Holiday home in Smithville

Loft in Wooster

Flat in Wooster

Flat in Apple Creek

Flat in Wooster

Home in Wooster

Townhouse in Orrville

Flat in Apple Creek

Holiday rentals for every style

Flats

Houses

Hotels

Popular amenities for Wooster holiday rentals

Stay near Wooster's top sights

Other great holiday rentals in Wooster

Guest house in Glenmont

Loft in Wooster

Cabin in Beach City

Home in Dalton

Guest house in Millersburg

Guest house in Ashland

Flat in Wooster

Flat in Wooster

Quick stats about holiday rentals in Wooster

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore