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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Winesburg vacation homes

Property grounds
Spacious 3BR Home w/ 8 Beds, Big Yard & Parking – Near Canton & Hall of Fame

Spacious 3BR Home w/ 8 Beds, Big Yard & Parking – Near Canton & Hall of Fame

Spacious 3BR Home w/ 8 Beds, Big Yard & Parking – Near Canton & Hall of Fame
Massillon
10.0 out of 10, Exceptional, (2)
"Just needed a place to shower and sleep close to a friends house, this worked out perfect."
United States
Tom P.
The price is AED 331
AED 880 total
includes taxes & fees
12 Dec - 13 Dec
Spacious 3BR Home w/ 8 Beds, Big Yard & Parking – Near Canton & Hall of Fame
Fridge, microwave, oven, stovetop
Newly Renovated Home in Canton

Newly Renovated Home in Canton

Newly Renovated Home in Canton
Canton
10.0 out of 10, Exceptional, (5)
"Great property centrally located for all of our adventures. Hosts were great and very easy to communicate with. Definitely on the lists of places to return too!"
United States
Deanna B.
The price is AED 298
AED 665 total
includes taxes & fees
15 Dec - 16 Dec
Newly Renovated Home in Canton
Fridge, microwave, oven, dishwasher
Amish Country Getaway w/ Pastoral Views!

Amish Country Getaway w/ Pastoral Views!

Amish Country Getaway w/ Pastoral Views!
Millersburg
9.4 out of 10, Exceptional, (19)
"Beautiful country. Home as described and great for two couples."
United States
Deborah P.
The price is AED 320
AED 941 total
includes taxes & fees
21 Dec - 22 Dec
Amish Country Getaway w/ Pastoral Views!
Property grounds
Hollow Valley Crates

Hollow Valley Crates

Hollow Valley Crates
Sugarcreek
10.0 out of 10, Exceptional, (23)
"We really enjoyed our stay. We only stayed 1 night, would like to come back again for 2 nights! Loved the location and the views! Very quiet. Loved sitting out on the porch Friday evening enjoying nature. "
United States
Denis S.
The price is AED 380
AED 645 total
includes taxes & fees
21 Dec - 22 Dec
Hollow Valley Crates
Interior
The Farmhouse at 1885: Where Past Meets Present

The Farmhouse at 1885: Where Past Meets Present

The Farmhouse at 1885: Where Past Meets Present
Navarre
10.0 out of 10, Exceptional, (18)
"Great stay we truly enjoyed the porch area !"
United States
Jared R.
The price is AED 360
AED 1,025 total
includes taxes & fees
6 Jan - 7 January 2026
The Farmhouse at 1885: Where Past Meets Present
Terrace/patio
Grandma’s Place - Steps from Downtown Sugarcreek

Grandma’s Place - Steps from Downtown Sugarcreek

Grandma’s Place - Steps from Downtown Sugarcreek
Sugarcreek
10.0 out of 10, Exceptional, (77)
"Everything was perfect! Keeping this site for future stays. "
United States
Gisele W.
The price is AED 529
AED 922 total
includes taxes & fees
14 Dec - 15 Dec
Grandma’s Place - Steps from Downtown Sugarcreek
Exterior
Modern Amish Country Home, close to Berlin, Millersburg, Wooster, Loudenville.

Modern Amish Country Home, close to Berlin, Millersburg, Wooster, Loudenville.

Modern Amish Country Home, close to Berlin, Millersburg, Wooster, Loudenville.
Holmesville
10.0 out of 10, Exceptional, (18)
"Very clean and quiet. Excellent stay"
United States
Logan B.
The price is AED 397
AED 860 total
includes taxes & fees
22 Dec - 23 Dec
Modern Amish Country Home, close to Berlin, Millersburg, Wooster, Loudenville.
Exterior
Riverside Retreat with Hot Tub

Riverside Retreat with Hot Tub

Riverside Retreat with Hot Tub
Strasburg
10.0 out of 10, Exceptional, (111)
"Perfect stay for what we needed. "
United States
Anonymous traveler
The price is AED 404
AED 926 total
includes taxes & fees
8 Jan - 9 January 2026
Riverside Retreat with Hot Tub
Smart TV
Freda's Place

Freda's Place

Freda's Place
Dundee
10.0 out of 10, Exceptional, (55)
"Good location central to area tourist area but away from the crowds. Short walk to get a great trail bologna and cheese sandwich "
United States
JR B.
The price is AED 459
AED 569 total
includes taxes & fees
3 Jan - 4 January 2026
Freda's Place
Interior
Charming 2-bedroom townhome with WiFi, AC in downtown Orrville

Charming 2-bedroom townhome with WiFi, AC in downtown Orrville

Charming 2-bedroom townhome with WiFi, AC in downtown Orrville
Orrville
10.0 out of 10, Exceptional, (3)
"Place was very easy to find. My mother and I came up for a couple days to visit family. It was the perfect place for our overnight stay. Beautifully decorated. Felt like home. We would book again when we are planning to stay in the area!"
United States
Nicole K.
The price is AED 441
AED 672 total
includes taxes & fees
15 Dec - 16 Dec
Charming 2-bedroom townhome with WiFi, AC in downtown Orrville
Interior
Heritage House - Orrville, OH … minutes to Amish Country!

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

Heritage House - Orrville, OH … minutes to Amish Country!
Orrville
10.0 out of 10, Exceptional, (12)
"Our hosts were widely available for all communications and the house was exactly as described. We would stay again and appreciate the hospitality!"
United States
Erin G.
The price is AED 547
AED 621 total
includes taxes & fees
17 Dec - 18 Dec
Heritage House - Orrville, OH … minutes to Amish Country!
Outdoor spa tub
Rural, Amish Country, sleeps 6

Rural, Amish Country, sleeps 6

Rural, Amish Country, sleeps 6
Sugarcreek
10.0 out of 10, Exceptional, (21)
"Very nice, the country and farms in the area, plenty of horses in the fields.. the home is great the porch furniture is very comfy ..beds comfy.. very nice hosts.."
United States
Reva W.
The price is AED 442
AED 819 total
includes taxes & fees
18 Dec - 19 Dec
Rural, Amish Country, sleeps 6
Fridge, microwave, stovetop, coffee/tea maker
Gorgeous studio, sleeps 4, Amish country.

Gorgeous studio, sleeps 4, Amish country.

Gorgeous studio, sleeps 4, Amish country.
Millersburg
10.0 out of 10, Exceptional, (5)
"Beautiful property! Peaceful setting. Clean and comfortable accommodations with all the essentials. Wonderful location to get away from it all. Note: no TV or Wi-Fi (great opportunity to unplug for a few days)"
United States
Shellie A.
The price is AED 442
AED 807 total
includes taxes & fees
11 Dec - 12 Dec
Gorgeous studio, sleeps 4, Amish country.
1 bedroom, iron/ironing board, free WiFi, bed sheets
Eternal Romance: The Honeymoon Suite at 1885 Farms

Eternal Romance: The Honeymoon Suite at 1885 Farms

Eternal Romance: The Honeymoon Suite at 1885 Farms
Navarre
8.8 out of 10, Excellent, (23)
"This place was truly beautiful. The land around the site was great to walk...it was quiet and tranquil. The inside was very well done with top notch finishes. Truly beautiful upscakr farmhouse appeal!"
United States
Nicole K.
The price is AED 492
AED 926 total
includes taxes & fees
16 Dec - 17 Dec
Eternal Romance: The Honeymoon Suite at 1885 Farms
Terrace/patio
The Aspen . Trailside Lodging

The Aspen . Trailside Lodging

The Aspen . Trailside Lodging
Millersburg
10.0 out of 10, Exceptional, (22)
"Very clean, tastefully decorated and suited our needs wonderfully! Would recommend! "
United States
Liz H.
The price is AED 331
AED 654 total
includes taxes & fees
11 Dec - 12 Dec
The Aspen . Trailside Lodging
TV, fireplace
"30 Something" | Family & Business Friendly Stay

"30 Something" | Family & Business Friendly Stay

"30 Something" | Family & Business Friendly Stay
New Philadelphia
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay here. The home was clean and very comfortable. Will definitely stay here again for future visits!"
United States
Sarah H.
The price is AED 441
AED 1,177 total
includes taxes & fees
5 Jan - 6 January 2026
"30 Something" | Family & Business Friendly Stay
Smart TV
2 Br home with Hot-Tub! Quiet, dead end street

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, (142)
"Great location very clean and loved the hot tub "
United States
Patty C.
The price is AED 463
AED 773 total
includes taxes & fees
11 Dec - 12 Dec
2 Br home with Hot-Tub! Quiet, dead end street
Private kitchen
Cottage in Sugarcreek with Hot Tub

Cottage in Sugarcreek with Hot Tub

Cottage in Sugarcreek with Hot Tub
Sugarcreek
9.4 out of 10, Exceptional, (3)
"Very clean, nice setting. Host was very accommodating. "
United States
Teresa S.
The price is AED 422
AED 790 total
includes taxes & fees
11 Dec - 12 Dec
Cottage in Sugarcreek with Hot Tub
Fridge, microwave, oven, stovetop
Vivian's Serenity Guest House

Vivian's Serenity Guest House

Vivian's Serenity Guest House
Millersburg
10.0 out of 10, Exceptional, (16)
"We were in town for a grad party. The place was super cute and so much better than staying in a hotel. "
United States
Christy A.
The price is AED 565
AED 961 total
includes taxes & fees
11 Dec - 12 Dec
Vivian's Serenity Guest House
Fridge, microwave, oven, stovetop
Charming 3-bedroom house in Wooster with TV & WiFi

Charming 3-bedroom house in Wooster with TV & WiFi

Charming 3-bedroom house in Wooster with TV & WiFi
Wooster
9.6 out of 10, Exceptional, (5)
"Nice house with good space for gathering. Although the weather didn’t cooperate for us to use the outdoor space, it is nice. "
United States
Stacy V.
The price is AED 551
AED 1,072 total
includes taxes & fees
15 Dec - 16 Dec
Charming 3-bedroom house in Wooster with TV & WiFi
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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Top Winesburg Hotel Reviews

Berlin Grande Hotel

Berlin Grande Hotel

10/10 Excellent
"Spotless and spacious! Pool and hot tub were great! Pool is heated. Staff was courteous and super helpful."
Marie 1-night trip
Posted 3 days ago
Berlin Grande Hotel