Wooster Vacation Rentals

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Wooster vacation homes

A brick house with a white door and a 'WELCOME' sign. There are steps leading up to the door and a wooden railing on the left.

1. Cozy, cute home close to College of Wooster and Amish Country, Ohio

Cozy, cute home close to College of Wooster and Amish Country, Ohio
Wooster
9.8 out of 10, Exceptional, (29 reviews)
"We had a great stay and would recommend "
United States
Johnson D.
The price is CA $207
CA $431 total
includes taxes & fees
Nov 16 - Nov 17
Cozy, cute home close to College of Wooster and Amish Country, Ohio
A modern kitchen with wooden cabinets, a dishwasher, and a window. There is a green armchair and a small round table. A sliding glass door leads to a bathroom.

2. Modern Studio with BBQ Grill and Patio

Modern Studio with BBQ Grill and Patio
Creston
The price is CA $150
CA $372 total
includes taxes & fees
Dec 1 - Dec 2
Modern Studio with BBQ Grill and Patio
A modern kitchen with white cabinets, a stainless steel dishwasher, and a window with a view of the outdoors.

3. Quiet 2BR Retreat with Patio and Grill

Quiet 2BR Retreat with Patio and Grill
Creston
Quiet 2BR Retreat with Patio and Grill
A living room with a sofa, coffee table, and a view of the outdoors through large windows.

4. Bright 2BR home with private entrance

Bright 2BR home with private entrance
Creston
The price is CA $187
CA $451 total
includes taxes & fees
Dec 1 - Dec 2
Bright 2BR home with private entrance
A covered porch with two green Adirondack chairs and a small round table, a mailbox, and a door with a number 804 sign.

5. Heritage House - Orrville, OH … minutes to Amish Country!

Heritage House - Orrville, OH … minutes to Amish Country!
Orrville
10.0 out of 10, Exceptional, (20 reviews)
"We had a wonderful stay at Heritage House. Our family was in town for Fire in the Sky & the location of the home was amazing. The house was very clean and the beds were comfortable. Cheryl & Tom were very responsive whenever we had questions. Highly recommend the heritage house if you are planning a trip to Orrville!"
United States
Gerri C.
The price is CA $210
CA $303 total
includes taxes & fees
Nov 16 - Nov 17
Heritage House - Orrville, OH … minutes to Amish Country!
A front door with a 'B' marking, a small sign reading 'Vintage Travel Suite', a mailbox, a window with shutters, and a doormat.

6. Charming home with BBQ grill

Charming home with BBQ grill
Creston
The price is CA $163
CA $425 total
includes taxes & fees
Nov 22 - Nov 23
Charming home with BBQ grill
An outdoor deck with a sectional sofa and a small table.

7. Orrville Getaway | Hot Tub + Outdoor Living

Orrville Getaway | Hot Tub + Outdoor Living
Orrville
The price is CA $397
CA $713 total
includes taxes & fees
Nov 16 - Nov 17
Orrville Getaway | Hot Tub + Outdoor Living
A wooden deck with wicker furniture, including two chairs and a bench, and a potted plant.

8. Honey Run King Suite ~between Millersburg & Berlin

Honey Run King Suite ~between Millersburg & Berlin
Millersburg
9.8 out of 10, Exceptional, (24 reviews)
"Great stay, clean house, very quiet place."
United States
Gahriman B.
The price is CA $198
CA $274 total
includes taxes & fees
Nov 17 - Nov 18
Honey Run King Suite ~between Millersburg & Berlin
A hot tub with a clear view of a pond and gazebo in the background.

9. Amish Country Getaway w/ Hot Tub & Views

Amish Country Getaway w/ Hot Tub & Views
Applecreek
9.6 out of 10, Exceptional, (15 reviews)
"Amazing property!"
United States
Ruth P.
The price is CA $508
CA $755 total
includes taxes & fees
Nov 16 - Nov 17
Amish Country Getaway w/ Hot Tub & Views
A front door with a dark door, a wreath, and a potted plant on either side.

10. The Towpath Retreat: A Cozy Farmhouse Stay

The Towpath Retreat: A Cozy Farmhouse Stay
Canal Fulton
9.8 out of 10, Exceptional, (75 reviews)
"Such a cute house! Loved our stay here!"
United States
Ashley Q.
The price is CA $148
CA $280 total
includes taxes & fees
Nov 18 - Nov 19
The Towpath Retreat: A Cozy Farmhouse Stay
A log cabin with a porch, surrounded by a well-maintained lawn and trees.

11. Romantic Amish Country Cabin w/ Hot Tub & Jacuzzi

Romantic Amish Country Cabin w/ Hot Tub & Jacuzzi
Millersburg
10.0 out of 10, Exceptional, (51 reviews)
"We love staying here every time we come into the area. It’s perfect and peaceful."
United States
Rikki H.
The price is CA $298
CA $487 total
includes taxes & fees
Nov 16 - Nov 17
Romantic Amish Country Cabin w/ Hot Tub & Jacuzzi
A house with a covered porch, outdoor seating, and a view of the landscape.

12. Spacious 2 BR home, just minutes from Berlin, OH.

Spacious 2 BR home, just minutes from Berlin, OH.
Millersburg
9.6 out of 10, Exceptional, (18 reviews)
"Nice place, would do it again"
United States
Gary
The price is CA $179
CA $348 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 2 BR home, just minutes from Berlin, OH.
A bedroom with a bed, bedside tables, a lamp, a decorative wall piece, and a green armchair.

13. Country Retreat with Scenic Farm Views

Country Retreat with Scenic Farm Views
Dalton
9.6 out of 10, Exceptional, (9 reviews)
"A great property and perfect for our stay. We really enjoyed the location and the tranquil atmosphere."
United States
Ron Z.
The price is CA $478
CA $705 total
includes taxes & fees
Nov 20 - Nov 21
Country Retreat with Scenic Farm Views
A hot tub with a control panel, set against a house with siding and a window.

14. 2 Br home with Hot-Tub! Quiet, dead end street

2 Br home with Hot-Tub! Quiet, dead end street
Millersburg
10.0 out of 10, Exceptional, (177 reviews)
"Such a nice area."
United States
Jack V.
The price is CA $186
CA $295 total
includes taxes & fees
Nov 23 - Nov 24
2 Br home with Hot-Tub! Quiet, dead end street
A house with a front door, a fire pit, outdoor seating, and a garden.

15. The Aspen . Trailside Lodging

The Aspen . Trailside Lodging
Millersburg
10.0 out of 10, Exceptional, (22 reviews)
"We enjoyed the secluded location yet easy access back into Millersburg. The weather was great."
United States
Ron S.
The price is CA $160
CA $287 total
includes taxes & fees
Nov 16 - Nov 17
The Aspen . Trailside Lodging
A two-story house with a covered patio, outdoor seating, and a small garden.

16. Large Group Retreat w/ Indoor Pickleball

Large Group Retreat w/ Indoor Pickleball
Dalton
9.4 out of 10, Exceptional, (9 reviews)
"This house was great! Our group had a wonderful time and loved that there were so many places that we could gather together. Enjoyed the pickle ball court too! "
United States
Jessica S.
The price is CA $2,401
CA $3,155 total
includes taxes & fees
Nov 16 - Nov 17
Large Group Retreat w/ Indoor Pickleball
A patio area with wicker furniture, a glass-top table, and a view of a lush garden.

17. Charming Retreat, Cozy Fireplace, Private Porch, Minutes to Amish Country

Charming Retreat, Cozy Fireplace, Private Porch, Minutes to Amish Country
Millersburg
9.8 out of 10, Exceptional, (40 reviews)
"Great place, very well decorated!!"
United States
Bobbiejo P.
The price is CA $208
CA $351 total
includes taxes & fees
Nov 24 - Nov 25
Charming Retreat, Cozy Fireplace, Private Porch, Minutes to Amish Country
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18. Escape To Our Clean Quiet Fully Furnished Cabins Nestled In Amish Country

Escape To Our Clean Quiet Fully Furnished Cabins Nestled In Amish Country
Dundee
10.0 out of 10, Exceptional, (312 reviews)
"This place is very nice and clean! The breakfast was delicious and worth getting!"
United States
Bethany B.
The price is CA $225
CA $303 total
includes taxes & fees
Nov 16 - Nov 17
Escape To Our Clean Quiet Fully Furnished Cabins Nestled In Amish Country
A storage closet with shelves holding folded blankets, a basket, and a white container.

19. Charming Century House - Next Door to Ashland University

Charming Century House - Next Door to Ashland University
Ashland
10.0 out of 10, Exceptional, (135 reviews)
"Very clean and comfortable. Just a quick stay overnight while traveling. Would definitely stay again. Loved the downtown area!"
United States
Jimmy P.
The price is CA $178
CA $196 total
includes taxes & fees
Nov 16 - Nov 17
Charming Century House - Next Door to Ashland University
A deck with a table and chairs, a potted plant, and a large umbrella.

20. Cozy 2-bedroom home in Winesburg, holmes county ohio

Cozy 2-bedroom home in Winesburg, holmes county ohio
Dundee
10.0 out of 10, Exceptional, (25 reviews)
"We got to enjoy the house for one night and found it to be very relaxing after driving around Amish Country all day. Very clean and homey."
United States
Jill R.
The price is CA $205
CA $301 total
includes taxes & fees
Dec 1 - Dec 2
Cozy 2-bedroom home in Winesburg, holmes county ohio
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Learn more about Wooster

Stroll through downtown's charming streets, where local shops and eateries surround the historic courthouse square. Explore Amish country nearby, then return to Wooster for a show at the Ohio Light Opera or a tour of the College of Wooster's campus.

See all hotels in Wooster
A historic building with a clock tower, American flags, and a red stop sign.

Top reviews in Wooster

A spacious lobby with a check-in counter, seating area, and a second-floor balcony.
Comfort Suites Wooster near University Campus

Comfort Suites Wooster near University Campus

Comfort Suites Wooster near University Campus
Wooster

10/10 Excellent

Special thank for the desk manger of the evening shift
Canada
Wail
Reviewed June 14, 2026
Comfort Suites Wooster near University Campus

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