Vacation rentals in Windham

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Top-rated vacation rentals in Windham

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Guest favorite

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

4.87 out of 5 average rating, 54 reviews

Newton Falls Best

Your family will be close to everything staying at this 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. No pets allowed , NO Parties allowed

Top guest favorite

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, 166 reviews

Ma & Pa’s Romantic Private Cabin 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 Gas Fire pit, Spacious Kitchen, Outdoor Bath (No Jets) and all the Amenities including Wifi. Golfing, Skydiving, Cuyahoga Valley National Park, Nelson Ledges State Park, Amish Region. Adventure Awaits at Ma & Pa’s Cabin!

Guest favorite

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.

Apartment in Garrettsville

5 out of 5 average rating, 29 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 favorite

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, 453 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.

Superhost

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

4.83 out of 5 average rating, 234 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 favorite

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

4.9 out of 5 average rating, 41 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 favorite

The exterior of the Old Postal Cottage is showcased, featuring classic red brick and a welcoming sign depicting a horse. Dual white windows are framed by seasonal decorations, including a wreath and festive bow, while a sturdy railing and balcony enhance the quaint façade.

Tiny home in Parkman

4.99 out of 5 average rating, 201 reviews

The Old Postal Cottage

*Note: feel free to inquire about availability for dates not listed as open on calendar. The Old Postal Cottage, built in the 1840s, was the Parkman post office until mid 2018. It was completely renovated, and it is now a tiny house, located within an Amish community in Northeast Ohio. It has a private entrance, and is a cozy space, perfect for a getaway in the country, with access to all major roads and an easy commute to Cleveland, Youngstown, Akron, and many tourist attractions.

Guest favorite

The cozy living area features wooden walls and large windows with blinds, letting in natural light. A 55-inch television is positioned on a wooden stand, accompanied by a leather sofa, a patterned armchair, and a vibrant table with four chairs, creating a welcoming space for relaxation.

Apartment in Youngstown

4.88 out of 5 average rating, 563 reviews

Woodland Oasis Cabin Apartment

Late Checkins are fine.This quaint Cabin style Apt is perfect for a quick stopover or longer stays.Having all the amenities you need at hand. This is a 575sq ft self contained apt .We are the perfect stop over being a half Way between Chicago and New York. 5 mins away from In I80 E or W ext 229 or route 711 ext 228a off Belmont ave ,5 min to St Elizabeth.Y.S.U, Covelli , Amphitheater 10 mins to Westside Bowl, fishing spots 5 mins away from Penguin city Brewery and past times arcade.

Top guest favorite

An open-concept living space features wood-paneled walls and a warm wooden floor. A spacious sectional sofa is situated across from a large wall-mounted television. A dining area with dark chairs surrounds a long table, and a rustic coffee table made from natural wood is placed on a textured rug.

Cabin in Cortland

4.97 out of 5 average rating, 193 reviews

Cheerful Cabin-Sleeps 5 - lake views + relaxation

This unique place has a style all its own. This adorable cabin is located steps away from Mosquito Lake, bars and restaurants, bait shops, public boat launch and minutes away from lovely wineries. Perfect for small families or couples. This cabin has been professionally designed and updated. Relax on the deck and listen to live music during the summer months. The sleeping space is a loft separated by a wall. Queen bed on one side, double bed and a single up top on the other side.

Top guest favorite

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, 436 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.

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, 718 reviews

The Triangle: A-Frame Cabin for your city retreat

Cabin retreat in the Village of West Farmington. This 400 sq. ft. A-Frame cabin is perfect for a weekend away from the city to relax, rejuvenate, and rest. The welcoming nature of the cabin is immediately apparent when you walk in - the wood-burning stove, the exposed beams throughout, and the many small details will draw you in to your weekend home. Brand new deck in Fall 2024! Extremely close to The Place at 534.

Guest favorite

The exterior of a wooden A-frame house is shown, featuring a sloped roof and multiple large windows. A wooden deck with a railing surrounds the entrance, while a small tree with autumn leaves stands in the foreground. The surrounding landscape includes green grass and distant trees.

Cabin in Southington

4.97 out of 5 average rating, 219 reviews

Cozy A-Frame Getaway Minutes from Nelson Ledges

Welcome to a new space for rest. You will be greeted with the coziness and peace of the nature without sacrificing luxury and convenience. Whether you decide to stay in and enjoy the hot tub, or get out and explore the ledges and quaint town of Garrettsville, you are sure to create lasting memories. We also provide top notch wifi and a designated workspace so working from home just got a whole lot comfier.