Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite

Guesthouse in Chardon

4.94 out of 5 average rating, 154 reviews

Chardon Loft

Large private studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels are provided. The furnace is nontraditional. It is open and not in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Jul 26 – Aug 2

G$18,850 GYD per night

Guest favorite

Guesthouse in Madison

4.95 out of 5 average rating, 166 reviews

LemonDrop Lake-Front Cottage

Fully remodeled in 2023 LemonDrop Cottage is a Lake-Front property, with direct access to Lake Erie. Lake viewable from Kitchen or Bedroom windows. Mar-2023 all New Windows, Bathroom doubled (2x) in size, new 12K AC. 2021-Hickory hardwood floors,, shower, hot water heater, oven, kitchen table/chairs, king size mattress, sofa-bed, BBQ grill (propane provided), and fire pit with wood provided. Built in 1949 as a fishing cottage, adorable Lake-Front Cabin with private stairwell down to the water.

Mar 12 – 19

G$28,692 GYD per night

Guest favorite

Cabin in Middlefield

4.98 out of 5 average rating, 166 reviews

Forever Spring Cabin

This is a beautiful, brand-new cabin in a quiet wooded setting with nature trails in historic Mesopotamia, Ohio. We are about 45 minutes from Youngstown and Cleveland. Amenities include coffee, tea, juice, soda, cereals, snacks, pancake mix, and even maple syrup gathered in our own local woods. Relax and unwind at the end of the day in our whirlpool for two. Or sit on the porch and enjoy the peaceful surroundings of nature. Continental breakfast only. Outdoor campfire with firewood provided.

Sep 29 – Oct 6

G$35,497 GYD per night

Guest favorite

Home in Garrettsville

5.0 out of 5 average rating, 304 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.

Nov 1 – 8

G$54,522 GYD per night

Guest favorite

Cabin in Burton

4.93 out of 5 average rating, 107 reviews

Romantic Cozy Getaway Cabin with Outdoor Bath

Nestled in the Woods of Geauga County is the home Ma & Pa’s Cabin. An Off the Grid 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. Adventure Awaits at Ma & Pa’s Cabin!

Apr 28 – May 5

G$33,845 GYD per night

Guest favorite

Tiny home in Parkman

4.99 out of 5 average rating, 179 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.

May 7 – 14

G$23,205 GYD per night

Superhost

Cabin in West Farmington

4.9 out of 5 average rating, 602 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. Grab some berries and wildflowers that bloom around the cabin! Extremely close to The Place at 534. Find us on social - @thetrianglecabin

Feb 27 – Mar 6

G$19,932 GYD per night

Guest favorite

Tiny home in Burghill

4.97 out of 5 average rating, 201 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.

Jun 26 – Jul 3

G$14,307 GYD per night

Superhost

Farm stay in Chardon

4.87 out of 5 average rating, 288 reviews

Bonnie's Guesthouse @ Peridot Equine Sanctuary

***ALL PROFITS SUPPORT THE HORSES OF PERIDOT EQUINE SANCTUARY*** The rustic decor and well lit space reflects the nature of our horse farm & sanctuary, where you can stay for a peaceful country getaway. We're rural, but you'll still have easy access to lots of amenities in the wonderful nearby town of Chardon, less than 10 minutes away. Cleveland itself, currently going through a "rustbelt renaissance" is only about 45 minutes minutes West. We welcome guests of all backgrounds!

Oct 27 – Nov 3

G$32,191 GYD per night

Guest favorite

Barn in Kinsman

4.98 out of 5 average rating, 223 reviews

Cozy Cabin in Kinsman

This is a western themed, open concept cabin. The cabin is the upper level of a barn-like structure, separated from our home by a large patio. It has a Loft and a Sleep n’ Play Hideaway for children. (The double bed inside the Hideaway is suitable for teens and even adults.) Our cozy cabin is perfect place for either a couple, a few friends or a family. It is also a wonderful place for a retreat or a place to work away from home or the office. (See photos for clarity of layout.)

Nov 9 – 16

G$21,246 GYD per night

Guest favorite

Apartment in Madison

4.94 out of 5 average rating, 109 reviews

Cozy winery get away with year round hot tub.

Relax in this cozy country garage apt. in Grand River Valley. The first stop on your winery tour is just 4 minutes away with over 30 more to explore. Visit nearby Lake Erie, Thompson Ledges, Geauga Park District Observatory, or a covered bridge. Kitchenette w/ mini fridge, microwave, Keurig & sink. Quaint bath w/ stand up shower Private keycode entry Electric fireplace King size bed Rustic wood rockers & table Pet friendly Shared access to hot tub, back yard fire pit & patio

Oct 25 – Nov 1

G$17,325 GYD per night

Guest favorite

Guest suite in Perry

4.97 out of 5 average rating, 313 reviews

THE KELBY: Private Spacious Suite Near Grand River

Artfully decorated and resort-like, Kelby ABNB. is an absolute gem! It is a 1000 sqft loft on 3 acre wooded ravine: scenic vista with many windows. Half mile from outdoor YMCA trails. Owner provides list of favorite local haunts. Exceptionally clean&fresh.Visit wineries, hike, kayaking, antique stores. Kitchenette/breakfast area with amenities: juice, cereal, breakfast bars, etc. Warm comforters and down pillows, towels, and toiletries provided. Private. Quiet. Comfortable.

Dec 14 – 21

G$19,482 GYD per night