Holiday rentals in Windham

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Top-rated holiday rentals in Windham

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Top guest favourite
Cabin in Middlefield
4.96 out of 5 average rating, 105 reviews

The Wildflower

Come enjoy this brand new cabin in a private wooded setting. Sit on the front porch swing or relax by the fireplace. Enjoy the whirlpool for two and new stylish decor with black metal railing against a backdrop of the finest craftsmenship of woodworking. This cabin was built by local Amish and Mennonite builders. There is a double reclining loveseat and a queen size pull out sofa with a memory foam mattress. We provide snacks, sodas, coffee, tea, cereal, juice, pancaKe mix & maple syrup!

Top guest favourite
The exterior of a modern ranch house is showcased, featuring a vibrant red façade and a metal roof. A spacious deck is visible, complete with outdoor seating and a view of the nearby creek and surrounding trees. A gravel driveway leads to the entrance.
Home in Garrettsville
4.99 out of 5 average rating, 509 reviews

“Willow Ledge at Silver Creek”with Private Hot Tub

New Construction Modern Ranch House features rustic upscale design with beautiful cozy interiors and comfort at every turn. Stunning views await with floor to ceiling windows overlooking beautiful Silver Creek and surrounding nature. Private deck is spacious and inviting with oversize hot tub, concrete fire pit, gas grill, and outdoor dining furniture. A few minutes from great restaurants, the Brewery at Garrett’s Mill, and the coolest Coffee Shop. Perfect weekend getaway or business stay.

Guest favourite
A cozy A-Frame cabin is illuminated by string lights, creating a warm ambiance against the nighttime backdrop. The front porch features inviting seating, surrounded by trees and a tranquil yard. A nearby outbuilding is visible, hinting at a serene outdoor space for relaxation.
Cabin in West Farmington
4.84 out of 5 average rating, 270 reviews

bohemian stAyframe

Take it easy at this unique and tranquil getaway in the small village of West Farmington. This 1050 sq. ft. cosy A-Frame allows you to relax and reset at this perfect getaway away from the city. Warm up in front of the retro fireplace - main furnace heats the cabin well. Fun vibes with the bridge walkway and the many small bohemian details. 5 min walk down a country road you’ll find your way to a peaceful lake that you’ll have access to fishing/kayaking/paddle boarding. Sauna/Hot tub are hot!

Top guest favourite
A warm entryway is presented with a dark accent wall. A wooden bench is paired with hooks for coats and bags, creating an inviting first impression. Storage cabinets are neatly arranged on one side, complemented by greenery in a vase.
Flat in Mantua
5 out of 5 average rating, 117 reviews

Inclusive Breakfast + Coffee from R44 Coffee Shop!

Cozy up with INCLUSIVE coffee + breakfast from R44 Coffee Shop every day of your stay! Step into the comfort of this recently renovated 2BR (*Optional 3rd BR in living room with our sleek Murphy Bed!) 1.5Bath apt in the charming town of Mantua, OH. ✔ 2 Comfortable BRs (*optional 3rd BR in living room with our Murphy Bed!) ✔ Open Design Living ✔ Full Kitchen ✔ Complimentary Breakfast & Coffee ✔ Small Porch ✔ High-Speed Wi-Fi ✔ Smart TV ✔ Washer/Dryer ✔ Free Parking + EV Charging (220 Outlet)

Top guest favourite
The cabin constructed from shipping containers is surrounded by greenery, featuring a covered patio with hanging planters. An outdoor seating area with Adirondack chairs and a fire pit is visible in the foreground, alongside a hot tub partially obscured by the building.
Shipping container in Lisbon
5 out of 5 average rating, 133 reviews

Shipping Container Cabin with hot tub!

Enjoy our secluded getaway, that's not too far away! This cabin is made from three combined shipping containers to create one memorable experience for our renters. Housed on ten acres on Beaver creek and surrounded by nature's beauty, this rental is sure to give you the adventure and relaxation you need. Enjoy your favorite drink on one of two beautiful patios, by the fire inside or out, and end your evening in the warmth of our hot tub. Only 6 minutes from Route 11 in Lisbon, OH!

Top guest favourite
A rustic cabin, made of cedar, is nestled in the woods. The structure features a wrap-around deck and is surrounded by a serene pond and vibrant greenery. Purple flowers in the foreground enhance the natural setting, providing a peaceful atmosphere.
Cabin in Burton
4.93 out of 5 average rating, 185 reviews

Ma & Pa’s Romantic Cabin Fireplace Outdoor Bath

Nestled in the Woods of Geauga County is the home of Ma & Pa’s Cabin. A Getaway perfect for the weary traveler or great vacation spot! Surrounded by mature woods. Ma & Pa’s offers a unique adventure but just like home experience. Private, Hiking/Biking Trail, Fireplace, Outdoor Wood Fire pit, Spacious Kitchen, Outdoor Bath (No Jets) including Wifi. Golfing, Skydiving, Cuyahoga Valley National Park, Nelson Ledges State Park, Amish Region. Adventure Awaits at Ma & Pa’s Cabin!

Top guest favourite
A cozy living area features a comfortable gray sofa adorned with decorative cushions. A coffee table rests in front, and a television stands on a wooden stand. A brick fireplace serves as a focal point, surrounded by a subtle color palette and artwork.
Home in Mogadore
4.98 out of 5 average rating, 151 reviews

Amaryllis 3 BDR House Country Quiet near Kent OH

Amaryllis Guest House - a slice of country charm with lovely peaceful surroundings. Quiet, secluded home with country views and dark skies - great for birdwatching, golfing, hiking, relaxing. Guests from all walks of life are welcome, but absolutely no parties or events are allowed. Convenient for Kent (15 min), NEOMED (5 min), and Akron. Close to Dusty Armadillo, wineries, golfing, and hiking trails. Country peace and quiet but close enough to town for fine dining.

Top guest favourite
A rustic living area is featured with wood-paneled walls and a high, beamed ceiling. A patterned sofa and a recliner are positioned around a decorative area rug. A small electric fireplace adds warmth, while a TV hangs above the central seating. The room is adorned with a Christmas tree.
Cabin in Cortland
4.92 out of 5 average rating, 467 reviews

Cozy Countryside Cabin Near Multiple Wineries

Our cozy and inviting cabin, the Eagle's Nest, is nestled in a countryside setting behind Greene Eagle Winery and Brew Pub in rural Northeast Ohio. If you are looking for charm, and quiet relaxing comfort, this 384 sq. ft. cabin with exposed cedar beams is your perfect overnight or weekend retreat. Many activities available in the area with Mosquito lake nearby, bike trails, state park, golf, shopping, wineries, breweries, and restaurants within 10 to 30 minutes.

Top guest favourite
The exterior of a cottage features a welcoming entrance with a wooden deck, adorned with potted flowers. A bench provides a seating area, while greenery enhances the landscape. The cottage's siding showcases a neutral tone, and a gabled roof adds architectural interest.
Guest house in Middlefield
4.97 out of 5 average rating, 167 reviews

Little House on the Farm

The accommodation is a 2 bedroom cottage on our small farm that has been recently renovated. It is wheel chair accessible. We are in the middle of the fourth largest Amish community in the world. We are half a mile from the center of Mesopotamia, which is known for the End of the Commons General Store and the annual OX roast over the 4th of July. Cleveland and Youngstown are both approximately 45 minutes away. Lake Erie is 30 minutes north.

Top guest favourite
An open-concept living area features exposed brick walls and high ceilings with dark beams. A large island sits in the kitchen, while comfortable seating is arranged nearby. Multiple windows provide natural light and a view of the surroundings, enhancing the spacious feel of the loft.
Loft in Canal Fulton
4.99 out of 5 average rating, 371 reviews

Downtown Brick Loft Above The Exchange Coffee Co

Located in the heart of historic downtown Canal Fulton, this charming brick loft will truly take you back in time. Walk or bike to all the local restaurants and shops around town or grab coffee at The Exchange downstairs. The 13 large windows give a panoramic water view of the canal way and downtown. Every detail in this space has been lovingly created with comfort and inspiration in mind. Relax and enjoy this one of a kind location.

Guest favourite
Flat in Garrettsville
4.83 out of 5 average rating, 185 reviews

Historical Downtown Garrettsville, OHIO

Walking distance to restaurants, local shopping, a movie theater, and nightlife. Located on the river and on Main Street this home is just down the road from Hiram College. This apartment is one of a kind and great for couples, solo adventurers, business travelers, and families visiting loved ones in the area. There are few places for travelers to stay in the Garrettsville area and none as centrally located as this one.

Guest favourite
A comfortably furnished living area is highlighted by a blue sofa adorned with decorative pillows. A stone fireplace is situated beneath a large window, providing natural light. A round coffee table rests on a patterned area rug, complemented by soft lighting from nearby lamps and a tasteful side table.
Cottage in Lake Milton
4.94 out of 5 average rating, 203 reviews

A Romantic Lake Cottage, Lake Milton, Ohio

Welcome to our Lake Escape at Lake Milton. Our 2 bdm/1 bath cottage is available for up to 4 Family members to relax and enjoy the beauty of Lake Milton just across the street. We have installed the latest amenities, e.g. Roku HDTV w/Bose Soundbar, USB Charging wall outlets, Wifi, Soaking tub, Separate Shower, Toto Washlet, Air Fryer, Gas range, Central AC/heat, BBQ Grill, Gas fireplace, Bose Spkr500 w/Alexa.

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