Vacation rentals in Windham

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windham

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Newton Falls

4.87 out of 5 average rating, 46 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

An inviting outdoor space is shown, featuring a large hot tub surrounded by a spacious deck. A fire pit sits nearby, and a gas grill stands ready for use. Two chairs and a round table are positioned to create a comfortable gathering area.

Home in Garrettsville

4.99 out of 5 average rating, 427 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 unique retro fireplace is featured in the center of the room, set on a stone base. The fireplace adds warmth to the inviting living space, which showcases wood-paneled walls and an open kitchen area in the background. The cozy atmosphere is enhanced by a plush carpeted floor.

Cabin in West Farmington

4.85 out of 5 average rating, 221 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 cozy seating area is positioned in front of two large windows, offering an abundance of natural light. A comfortable black leather chair is paired with a stylish ottoman, while a floor lamp provides additional illumination. A potted plant adds a touch of greenery to the space.

Apartment in Mantua

5 out of 5 average rating, 90 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)

Guest favorite

A welcoming entryway features patterned tile flooring, bordered by dark mats. The walls are painted a soft gray, accented by black window treatments on three windows. A round white chair sits near the entrance, illuminated by a central light fixture.

Home in Newton Falls

4.91 out of 5 average rating, 32 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 front view of the Old Postal Cottage showcases its charming brick facade and welcoming porch. Lush greenery surrounds the exterior, and a flag can be seen displayed. A cloudy sunset sky adds a gentle glow, enhancing the inviting atmosphere of the residence.

Tiny home in Parkman

4.98 out of 5 average rating, 195 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

A welcoming front door with a glass panel is adorned with a seasonal wreath featuring sunflowers and autumn foliage. Flanking the door are two decorative pumpkins, positioned on rustic wooden pedestals. A textured doormat is situated below, enhancing the inviting entrance.

Apartment in Youngstown

4.88 out of 5 average rating, 543 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

A serene campfire scene displays vibrant flames flickering above a stack of logs, surrounded by rocks. Two individuals are seated nearby, hands intertwined, enjoying the warmth of the fire. The surrounding area features natural ground covered in leaves and grass.

Tiny home in Burghill

4.97 out of 5 average rating, 248 reviews

The Creekside Cottage

The Creekside Cottage is quietly located on our 240 acre property. If you're looking for a quiet "get-away" then our quaint, studio cottage is for you. We have a queen bed. Outside, we have a fire ring with firewood, grill, outdoor seating, and beautiful view. We DO NOT have TV/internet, or WiFi, although most phones get service. There is a small kitchenette but there is NO oven/stove. We DO have a toaster oven, microwave, mini-fridge, coffee pot Keurig, coffee pods, and bottled water.

Guest favorite

A compact bathroom features wood-paneled walls and a shower area enclosed by a white curtain. A white toilet is positioned beside a small window, allowing natural light. Fresh towels are neatly arranged, and a decorative wall sign adds a subtle touch to the wooden decor.

Cabin in Cortland

4.91 out of 5 average rating, 411 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 favorite

Home in West Farmington

5 out of 5 average rating, 8 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.

Superhost

A serene view of a water feature with gentle waterfalls cascading over smooth rocks. Lush greenery frames the scene, while a footbridge is visible in the background, enhancing the natural setting near the river.

Apartment in Garrettsville

4.83 out of 5 average rating, 173 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.

Superhost

The A-Frame cabin is nestled among tall trees, with a triangular roof and a welcoming entryway. A small deck is seen in front, surrounded by a lush green forest, providing a serene atmosphere for relaxation and exploration.

Cabin in West Farmington

4.9 out of 5 average rating, 694 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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Windham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Windham

Guest favorite

The kitchen counter features a coffee maker beside two white cups. A waffle maker is visible on the left. A drawer below is partially open, revealing an assortment of coffee creamers in various colors placed neatly within.

Condo in Warren

4.91 out of 5 average rating, 126 reviews

Beautiful Executive Suite - Howland

DeniseRating, 5 stars6 days ago

We very much enjoyed these accommodations. Felt safe and at home. Clean, spacious. Amazing shower! Lots of clean linens. Washer with soap and dryer super convenient. Look forward to another stay!

A serene creek flows through a wooded area, flanked by tall trees and lush greenery. Sunlight filters through the leaves, creating dappled light on the water's surface. A rocky bank leads to the clear water, inviting fishing and swimming experiences.

Home in Berlin Center

4.71 out of 5 average rating, 7 reviews

Retreat on Lake Milton

MatthewRating, 5 stars1 month ago

Great place to stay at if traveling with a dog and/or dogs. If I am ever in the area again, I’ll definitely try to book here. Many thanks.

Top guest favorite

A charming house with light gray siding is complemented by a welcoming front porch. A neatly manicured lawn is adorned with stones and shrubs. A driveway leads to a detached garage, featuring a parked car and an additional covered parking space.

Home in Niles

5 out of 5 average rating, 29 reviews

Charming 3 Bedroom Home

ThomasRating, 5 stars1 day ago

everything was great. was close to the restaurants and things to do. close to where I needed to go on Saturday. was an awesome experience at Suzanne's place. Definitely recommend this place.

The interior of a pine cabin features a high, wooden ceiling with exposed beams. Light-colored wooden walls create a warm ambiance. A pull-out sofa is positioned near a rustic wooden coffee table. Two windows, dressed in sheer curtains, allow natural light to enter the space.

Tiny home in Cortland

4.83 out of 5 average rating, 113 reviews

One Room Lakeside Cabin (Green Roof)

KikiRating, 5 stars3 weeks ago

We had so much fun! It was walkable to all of the nearby shops! Lisa’s place was so comfy and it had everything we needed for our Memorial Day weekend, a bbq grill, picnic table and a fire pit! 10/10!

A serene view of the calm Cuyahoga River captures reflections of lush greenery on its surface. The outdoor dock, framed by trees, offers direct access to the water, creating an inviting spot for relaxation and outdoor activities.

Apartment in Mantua

5 out of 5 average rating, 4 reviews

Crooked River Retreat

SarahroseRating, 5 stars1 month ago

I had a wonderful time here. My friend lives in Ohio and I live in NYC. I just found out I beat cancer and I started to just shut down in ny and this place was perfect. My body is still on the mend so we would go do something like see the troll doll museum (lol) and come back and be able to nap. The bathroom is Amazing with a lot of amenities and the river is very pretty. It was raining during our stay but we just cuddled up and rested. It was a perfect Place and the host was very kind and gave us a lot of Privacy.

Two wooden doors are displayed, featuring distinct paneling. Soft white towels hang on a polished metal rod, complementing the warm tones of the door finishes. A touch of greenery is seen above, adding a natural element to the setting.

Apartment in Leavittsburg

5 out of 5 average rating, 4 reviews

Quaint Lil Studio

KenRating, 5 stars4 weeks ago

Jeff's space was perfect for our short visit. Everything was exactly as pictured and was very new / clean throughout. We'd definitely book again next time we're in the area.

Top guest favorite