Holiday rentals in Windham

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Top-rated holiday rentals in Windham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Cabin in Cortland
4.83 out of 5 average rating, 99 reviews

Peaceful Rustic Entire A-Frame Cabin in the Woods

WELCOME! Leave your worries behind and relax on a country road in the heart of Northeast Ohio to this clean & peaceful cabin in the woods! Feed the birds and wildlife while the coffee is brewing and a warm fire crackling with firewood (supplied). Furnished with WiFi & TVs and utensils for all your cooking needs. Conveniently located just 6 min away from Mosquito lake, 12 minutes from Starbucks, Walmart,Quaker Steak and 22 minutes from the Eastwood Mall Complex. Book your reservation today!

Guest favourite
The exterior shows a single-story home nestled in a lush green landscape, surrounded by trees. A spacious backyard features well-maintained grass, with a patio area visible at one side of the house. The roof is covered in dark shingles, complementing the light-colored exterior.
Flat in Garrettsville
4.86 out of 5 average rating, 64 reviews

Woodside Estate

This property offers a safe and comfortable environment with a spacious (shared)backyard,acres of woods and blueberry patches and many other modern conveniences.Located in a quiet neighborhood and minutes from The Hiram College,The Brick,Garrett's Mill Brewing company and many other restaurants and coffee shops.Also located within minutes to headwaters bike trail. So wether you are just passing through or looking for a place to getaway and spend some time in the Country this is the place to be!

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, 570 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.

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
5.0 out of 5 average rating, 149 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)

Superhost
The A-Frame cabin stands among towering trees, showcasing its distinct triangular shape and large front deck. Surrounded by lush greenery, the wooden façade and black accents blend harmoniously with the natural environment, creating a sense of privacy and seclusion.
Cabin in West Farmington
4.89 out of 5 average rating, 785 reviews

The Triangle: Unplug in a Charming A-Frame

Step inside The Triangle & the outside world melts away. A wood-burning stove, exposed beams, and countless small details make this 400 sq ft A-Frame feel immediately like home. New deck (2024) perfect for morning coffee or evening stars. Nestled in Ohio's Amish Country - minutes from The Place at 534, Nelson-Kennedy Ledges, Observatory Park's dark skies, Holden Arboretum, and Burton Village. Exclusive music listening experience - a one of a kind cassette of my music available at the cabin.

Top guest favourite
A brick house with a sloped roof is showcased, featuring white framed windows and a welcoming porch. Lush green plants are positioned on either side of the entrance. A driveway leads to a garage with double doors, complemented by a manicured lawn and surrounding trees.
Home in Newton Falls
4.94 out of 5 average rating, 79 reviews

Cape Cod Retreat

Relax with the whole family here at the Cape Cod Retreat. Fenced in backyard to hang out and enjoy some bbq on the grill while watching the sunset! Fully furnished kitchen for your cooking and baking needs. Two living rooms with tvs and and area to enjoy playing games with your family and friends. This cozy little house is located a short walk (or drive) from downtown Newto n Falls where you can find lots of restaurants and antique shops as well as a waterfall and historic covered bridge.

Top guest favourite
A tri-level house is shown, featuring a light-colored exterior with a metal roof. A well-maintained lawn surrounds the property, with a large tree in the front yard and a gravel driveway leading to a two-car garage. Trees line the background.
Home in Bristolville
4.96 out of 5 average rating, 102 reviews

B’s Sunsets & Recreation

IMPORTANT! I DO NOT ALLOW WORK CREWS OR PETS DUE TO EXCESSIVE DAMAGES. We gladly welcome all others to come stay at our family friendly renovated tri-level with all the comforts of home and a private back yard with fire pit. We are within 5 minutes of Mosquito lake boat launch and Western Reserve Greenway bike trail. We are a 15 minute drive to The Place at 534 and great wineries. It is a 30 minute drive to Amish country or the Eastwood Mall Complex and Scrappers Stadium.

Top guest favourite
A covered porch features a comfortable seating arrangement with metal chairs around a low table. Hanging flower pots add a touch of color, while a patterned rug enhances the inviting atmosphere. A ceiling fan offers a refreshing breeze in this serene outdoor space.
Home in West Farmington
4.9 out of 5 average rating, 40 reviews

10 minutes from Nelson Ledges

You will be greeted with the peace and tranquility of country life without sacrificing luxury. This small but quaint farmhouse will give you the feel of warmth and love that was put into restoring every inch of this historical farmhouse. This perfectly imperfect family farmhouse located in Southington is the perfect getaway for a couple or a small family. This farmhouse has been in our family since early 1900's and is completely restored to its natural beauty.

Guest favourite
The exterior of a spacious two-story duplex is showcased, featuring a traditional white facade with blue shutters. A well-maintained lawn surrounds the property, complemented by a concrete pathway leading to the entrance. The home is positioned on a corner lot, with a welcoming porch visible.
Home in Newton Falls
4.88 out of 5 average rating, 67 reviews

Newton Falls Best

Centrally-located duplex. Quite neighborhood close to bars and restaurants in the center of Newton Falls, Ohio walking distance to the second oldest cover bridge in Ohio and a short drive to Lake Milton which provided boating , fishing, picnic area and playground. City Park just a block away - walking distance, enjoy, playground, tennis & basketball courts, baseball fields, skate ramps, and picnic area. Also available to rent attached duplex next door.

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, 184 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
A spacious century home is set against a backdrop of lush greenery and a manicured lawn. The building features a combination of traditional and modern architecture, with large windows allowing natural light and a welcoming front porch with wheelchair access.
Home in Newbury Township
4.96 out of 5 average rating, 352 reviews

Davis Ranch 5 Bedrooms Sleeps 10 & 3 1/2 baths

Overlooking Davis Lake, beautiful sunrises & 8 Acres. Will rent to 2 - 10 people on any given night. Guests will have the entire home as Host does not book more than one guest. No 1 Night stays please. Children under 2 there is no charge. Dogs no charge. I believe in making your stay a very memorable occasion. Please read the reviews that really tell the Ranch Story. In this Century Home you will have Three Full Baths and One 1/2 bath.

Superhost
Flat in Garrettsville
4.83 out of 5 average rating, 191 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.

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