Pet-friendly holiday rentals in Wooster

4.96 out of 5 average rating, 107 reviews

A covered porch with wooden beams provides a shaded area with a swing for three and two chairs. A gravel driveway leads to a neatly landscaped yard featuring green grass, a fire pit, and a shed in the background surrounded by trees.

Home in Millersburg

Lovely Private Home w/ Cozy Farmhouse Charm

Come away & enjoy a peaceful, refreshing stay at Vivian’s Serenity Guest House. Nestled in among the rolling hills of Amish Country, cozy up in the inviting house & explore local attractions. Only 1.5 miles from Rails to Trails biking trail, moments to historic downtown Millersburg, 10 minutes to Berlin shopping and great food! 1 mile to the Holmes County Fair Grounds. Whether you’re ready to shop unique boutiques or relax, Serenity House offers seclusion & proximity to all Amish country offers!

4.86 out of 5 average rating, 154 reviews

The exterior of a cozy apartment is illuminated at dusk, highlighting a welcoming entrance with steps and a covered porch. The soft glow of outdoor lighting enhances the wooden facade and surrounding greenery.

Apartment in Wooster

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!

4.98 out of 5 average rating, 148 reviews

A rustic cabin features earthy stonework and large windows, surrounded by lush greenery. Stone steps lead to a patio area adorned with planters. A vibrant red door adds a pop of color, while trees provide a natural backdrop, creating a serene environment.

Home in Fresno

Romantic private cabin w hot tub in Amish Country

Retreat to the Fresno Escape! A private cabin featuring a year-round hot tub, perfect for relaxation. Tucked among pines and rocks in the heart of Amish country, where the occasional clip-clop of horse and buggies adds charm. Styled like a railroad depot, the artistically furnished home displays intricate stonework, tile and custom stained glass. The kitchen includes appliances and cookware, with the outdoor area offering a propane grill. Complimentary firewood is provided for the firepit.

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.

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.

4.95 out of 5 average rating, 101 reviews

A charming entrance leads into a cozy cabin space. Light-colored wooden walls enhance the warmth of the room. A comfortable seating area is furnished with a striped blanket and a small heater. A bedroom door and a window, revealing natural light, provide an inviting atmosphere.

Tiny home in Wooster

Welcome to The Cabin at CT Farms!

Tiny-home, located on our 5.5 acre farm in western Wayne county. This brand-new cabin was constructed by local Amish builders. Complete with most amenities you'd find at home, it offers a cozy spot to relax or work. Have a cup of coffee on the porch and listen to the farmland awaken, or catch amazing sunsets in the evening. Located 2 minutes from US Route 30. 1.25 hours from Cleveland/Columbus. 10 minutes from College of Wooster. 30 minutes from Amish Country. (Berlin/Millersburg).

4.95 out of 5 average rating, 300 reviews

A well-maintained lawn surrounds the cabin, leading to a serene, spring-fed pond. Two trees provide shade for a hammock, creating a peaceful spot to relax. The greenery reflects the tranquil atmosphere of the property, inviting guests to enjoy the natural setting.

Cottage in Wooster

Cabin with pond & Fireplace * Hot Tub * King Bed

A quaint, cozy newly remodeled in 2025 cabin on 60 wooded acres perfect for a couples getaway. 8 minutes to a great downtown for shopping unique boutiques, dining, local wineries, breweries and distillery! Enjoy peace & tranquility in natures setting. Cozy up to a massive stone wood burning fireplace both inside and on the screened in porch. The brand new private hot tub boasts natural spring water and is just outside the door from the cabin and overlooks the natural spring ponds.

Guesthouse in Millersburg

A cozy cabin with a green metal roof is nestled among trees, featuring a welcoming porch with several wooden rocking chairs arranged for relaxation. A grassy area leads up to the entrance, inviting guests to enjoy the tranquil outdoor setting.

4.96 out of 5 average rating, 205 reviews

Cozy Retreat Tucked in the Heart of Amish Country

Welcome to heaven on earth! This cozy cabin tucked between the quiet woods and a beautiful scenic pond in the valley will have you wanting to cancel plans and lounge with a good book all day. Start your morning with coffee, rocking on the porch and bird watching over the pond. Spend the day exploring Berlin, Millersburg or Mohican (all within a very short drive). As the day turns into night, enjoy gooey marshmallows over the campfire while listening to the bullfrogs sing.

4.92 out of 5 average rating, 367 reviews

A quaint cabin entrance is framed by a covered porch, featuring wooden flooring and surrounded by vibrant potted plants. Two metal chairs provide seating, and a bold red door is prominently displayed, complementing the natural setting of greenery.

Cabin in Winesburg

Christi's Hideaway Cabin in Winesburg Ohio

Beautiful cabin sits back below our home. We are located in the beautiful town of Winesburg, Ohio within 5 miles of Mt. Hope , 6 miles from Walnut Creek & 7 miles from Berlin. Ohio. Within walking distance of Whitmer's general store & pizza and the Beacon Cafe. Come & visit our quaint little town and historical buildings. Our address is 2121 Main Street, Winesburg, Ohio 44690. You will have privacy! I have 2 outside cats but they never go inside.

Shipping container in Dover

A serene outdoor area features a gravel surface surrounding a fire pit, with several seating options including blue and brown chairs. A hot tub is positioned near a shaded structure, offering a peaceful setting among the lush greenery of the surrounding trees.

4.95 out of 5 average rating, 920 reviews

Riverside Hideout Shipping Container with Hot tub!

A unique oasis tucked into the woods & hills along Tuscarawas River. Mini kitchen, bedroom, bath & living room. Sit on the patio & take in the views of the river from the hot tub. Near Ohio/Erie Canal trail, ProFootball Hall of Fame, Amish Country Berlin & Walnut Creek, Atwood & Tappan Lake, Historic Zoar, Swiss Festival & Wineries. One pet is free, additional pets is $25 flat fee. You must claim a pet, for cleaning purposes.

Holiday home in Smithville

A bright living area features light green walls and two windows fitted with two-tone blinds. A dark coffee table sits at the center, surrounded by a gray sectional sofa adorned with checkered cushions. A wall clock and decorative art enhance the space, while a door leads outside.

4.85 out of 5 average rating, 227 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. 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.

4.95 out of 5 average rating, 208 reviews

Apartment in Wooster

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.

4.95 out of 5 average rating, 337 reviews

An outdoor seating area is framed by a gray fence, featuring a hot tub, a table with an umbrella, and two chairs. Potted plants add greenery to the space, which overlooks a grassy landscape, enhancing the atmosphere for relaxation.

Farm stay in Navarre

Amish Country Silo

Experience a one-of-a-kind romantic retreat in a charming grain bin with a modern farmhouse interior. This unique escape offers every amenity to ensure an unforgettable getaway. Gaze out the windows to take in the breathtaking views of the picturesque farmland. You're just 30 minutes from the heart of Amish Country, complete with the best shopping and restaurants!

Popular amenities for Wooster pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.92 out of 5 average rating, 118 reviews

The exterior entrance of the house features a covered porch with white railings and gray brick columns. A set of steps leads up to a blue front door, while manicured grass and mulch surround the entrance, creating an inviting atmosphere.

Home in Louisville

Charming 2BR Home

4.96 out of 5 average rating, 111 reviews

The exterior of a newly renovated house is presented, featuring a light blue facade and white trim. A covered porch extends along the front, with two chairs positioned nearby. A lush green lawn and well-maintained landscaping enhance the inviting appearance of the property.

Home in West Lafayette

Vineyard View Homestead

4.92 out of 5 average rating, 335 reviews

Home in North Hill

Entire home 10 minutes from Cuyahoga National Park

4.97 out of 5 average rating, 167 reviews

The exterior of a gray two-story house is visible, featuring a welcoming front porch with white railings. Large windows with dark blue shutters enhance the facade, while a brick pathway leads to the entrance. A small American flag is displayed near the porch.

Home in Medina

Medina 57 - Easy walk to Medina Historic District

4.9 out of 5 average rating, 168 reviews

A single-story house is visible, featuring a gray exterior and a black roof. Two small windows are positioned symmetrically on either side of the front door. A well-maintained lawn stretches in front, and tall trees are present in the background, adding to the natural setting.

Home in Wellington

Private Rochester Home

4.98 out of 5 average rating, 175 reviews

The property features a spacious arrangement of buildings with an inviting outdoor area, framed by a white fence. Autumn foliage is visible, adding color to the landscape. Nearby, a water tower and additional buildings can be seen against a cloudy sky.

Home in Sugarcreek

Horizon Haven | Family Getaway w/ Big Views

4.98 out of 5 average rating, 147 reviews

The exterior of a charming Cape Cod home is showcased, featuring yellow siding, a shingled roof, and decorative windows with red shutters. Lush greenery and blossoming flowers surround the entrance, while a carport and driveway are visible, providing convenient access.

Home in Akron

Sand Run Cape Cod - dog friendly

Superhost

A two-story farmhouse is surrounded by snow-covered trees, with a gently sloping roof and covered porch. A path leads to the front steps, and snow blankets the ground, creating a serene winter scene. Blue chairs are positioned on the porch, inviting relaxation.

Home in Killbuck

4.82 out of 5 average rating, 117 reviews

Secluded Holmes County Farmouse with fishing

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 141 reviews

An aerial view of a spacious lodge surrounded by lush greenery. A circular pool is positioned on a wooden deck, with a gazebo nearby housing a hot tub. Comfortable outdoor seating and a picnic area are visible in the yard, blending harmoniously with the natural landscape.

Cabin in Lucas

The Billy Pig Lodge- Pool / Hot tub / 7 acres!

4.88 out of 5 average rating, 60 reviews

An inground pool is visible, surrounded by a spacious patio area. A diving board is positioned at one end of the pool, while nearby, patio furniture includes a white chair set. Lush greenery and trees frame the background, adding to the peaceful setting.

Home in Akron

Guest House on Historic Merested Farms!

Superhost

An overview of the Pigskin Journeyman Vacation Rentals showcases a vibrant outdoor area featuring a pool, hot tub, and patio space. The collage highlights the Hall of Fame theme with football memorabilia, and cozy indoor spaces with modern amenities, including a gym and cinema.

Home in Massillon

4.55 out of 5 average rating, 38 reviews

Live the Game: Pool, Cinema, Gym, Jersey Wall

4.9 out of 5 average rating, 216 reviews

A cozy living area is highlighted by a stone fireplace and a wood-beamed ceiling. A spacious jacuzzi tub is positioned nearby, while two comfortable seating arrangements create a welcoming atmosphere. Soft lighting is provided by table lamps, and a large window allows natural light to enter.

Cottage in Millersburg

Romantic Cottage With Jacuzzi Fireplace

4.99 out of 5 average rating, 201 reviews

The exterior of Liberty Hill Lodge is presented from an aerial perspective, highlighting the spacious layout and landscaped grounds. A fenced-in heated pool is seen in the backyard, surrounded by lounge chairs and shaded seating areas. Lush greenery offers a peaceful and inviting outdoor environment.

Home in New Philadelphia

Liberty Hill Lodge, Hot Tub & Pool

4.91 out of 5 average rating, 164 reviews

The cabin features a covered front porch with wooden railings and log pillars, surrounded by a manicured lawn and mature trees. Natural light fills the exterior, showcasing rustic wooden siding and a metal roof, while providing a serene view of the surrounding landscape.

Cabin in Berlin

Cozy Cabin with Fireplace, Kitchen, Jacuzzi Tub

Superhost

An indoor pool measuring 25 yards is featured, with lanes marked for swimming. The area is well-lit, with blue and white banners hanging from the ceiling. Adjacent, a small pool area is visible for rental use, suitable for private gatherings. The environment is designed for family activities.

Condo in Apple Valley

4.83 out of 5 average rating, 6 reviews

Apple Valley Condos, by the AV Golf Course!

4.9 out of 5 average rating, 30 reviews

A welcoming outdoor space features a sparkling pool surrounded by lounge chairs and decorative plants. The log cabin is showcased in the background, adorned with warm string lights. A large umbrella offers shade, enhancing the relaxed atmosphere of this serene retreat.

Cabin in Butler

Relaxing Log Cabin | Hot Tub, Quiet, Pool, Mohican

Private, pet-friendly home rentals

4.97 out of 5 average rating, 35 reviews

Millie's Place Welcomes You!

The exterior of a two-story home built in 1920 is visible, featuring a light-colored facade with contrasting trim. A welcoming front porch provides seating, while a gravel path leads to the main entrance. Lush greenery and a manicured lawn complement the relaxed atmosphere.

4.84 out of 5 average rating, 58 reviews

Spink Street Extended Stay Craftsman Home.

4.95 out of 5 average rating, 65 reviews

A welcoming porch features a wooden deck with two chairs and a small table. Sunlight filters through surrounding greenery, and wooden posts support a roof overhead. Decorative lanterns hang, enhancing the outdoor charm. The peaceful setting offers a serene entry point to the cabin.

Cabin in Butler

Rugged Luxe: Hot tub; and (Summertime) Party Barn

5 out of 5 average rating, 44 reviews

A comfortable living area is furnished with two light-colored sofas, a decorative side table, and a flat-screen television mounted on the wall. A large area rug covers the wooden floor, while natural light enters through the windows, illuminating the space.

Home in Orrville

The Guesthouse at Elm Run Farms

4.98 out of 5 average rating, 55 reviews

A charming exterior view of a red cabin is showcased, featuring a covered porch supported by wooden beams. The porch is adorned with hanging plants and contains comfortable seating. Surrounding greenery adds to the tranquility of the landscape, complemented by a gently sloping grassy area.

Cabin in Big Prairie

Walton Nut Grove

5 out of 5 average rating, 18 reviews

A cozy bedroom showcases a spacious bed with decorative pillows and a light blanket. Two framed artworks adorn the walls, while a floor lamp provides warm illumination. A dresser with drawers is positioned nearby, and a wooden door adds character to the space.

Apartment in Wooster

Charming 1-BR Apartment Walking distance to COW

4.99 out of 5 average rating, 84 reviews

A cozy sleeping area features a spacious bed with neutral linens and decorative pillows. Two bedside tables with lamps provide gentle lighting. Soft, textured carpeting enhances comfort, while natural light filters in through the windows adorned with woven shades.

Home in Jeromesville

Peaceful 3-Bedroom Countryside Home Near Mohican