Windham Holiday Rentals

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Holiday Rentals in Windham

Sunset cottage complete w/large deck, fire pit and mins away from public beach

9.2 out of 10, Wonderful, (57)
"Group of four with two boats. Plenty of room for one rig in the driveway and the other along the street in front of the house. Both were plenty close enough to plug in and charge batteries at night."
Sunset cottage complete w/large deck, fire pit and mins away from public beach

Waterfront Home on Lake Milton: Dock, Hot Tub

9.6 out of 10, Exceptional, (15)
"Property is in a nice quiet location in a no wake zone. House is very nice just needs a few items to make it excellent. Kitchen needs additional cooking utensils, outdoor grill needs replaced - burners only worked in a couple spots other than that we really enjoyed our stay and will definitely rent again. "
Waterfront Home on Lake Milton: Dock, Hot Tub

Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country

9.8 out of 10, Exceptional, (21)
"Perfect place for all 24 of us to enjoy a few days away! "
Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country

Walk to Downtown Kent - 3 BR House w/ Patio & Yard

10.0 out of 10, Exceptional, (3)
"We stayed in Kent for a week and were helping to care for my 16 and 8 year old grandsons while my daughter (who lives in Kent) was having surgery. The location was excellent, we were able to walk many places (restaurants, library) and take field trips to beach, aquarium, and mini golf. The home was clean, comfortable, roomy, we made meals, enjoyed home’s board games and books, pitcher of filtered water in frig was a nice touch!"
Walk to Downtown Kent - 3 BR House w/ Patio & Yard

Lake Milton Ohio, Lakefront Vacation Rental, 4 Bedrooms, 3 Bath, Private Dock

9.6 out of 10, Exceptional, (132)
"Met the need for a family Christmas gathering!Overall a very spacious with more than ample room for 9 people. The kitchen was well appointed and met every need we had. Plenty of space for the kids to spread out in the basement and take advantage of bumper pool and video game. The bathrooms were clean and the hot water tank held out!! Overall would recommend John’s place again, and would be looking to check availability when the biggest amenity, the lake can be utilized."
Lake Milton Ohio, Lakefront Vacation Rental, 4 Bedrooms, 3 Bath, Private Dock

Loft Unplugged w/ Outdoor Space in Amish Country!

9.4 out of 10, Exceptional, (28)
"This was exactly what we needed over the holiday weekend! Thank you!!"
Loft Unplugged w/ Outdoor Space in Amish Country!

Conveniently located 2 bedroom home only minutes from hiking and state park fun!

10.0 out of 10, Exceptional, (92)
"All the comforts of home conveniently located for visiting family. The host is very accomodating even left the porch light on for us as we arrived after dark. We will definitely return. "
The price is AU$263
includes taxes & fees
19 Feb - 20 Feb
Conveniently located 2 bedroom home only minutes from hiking and state park fun!

Forever spring cabin

10.0 out of 10, Exceptional, (212)
"Our second time here and as good as the first. Very quiet and cozy. Would recommend."
Forever spring cabin

Luxurious Historic Victorian

9.6 out of 10, Exceptional, (4)
"The house was clean, easy to check into and was spacious. The beds were really soft and comfortable and the big seating area in the living room allowed us to congregate to talk and hangout. It was very well stocked with shampoo, body wash, paper towels, toliet paper, laundry soap, coffee, spices and almost anything else you could have wanted. There was plenty of parking for 4 - 6 cars behind the house. Our only mishap was we ended up being double booked on our last day and had another family...
Luxurious Historic Victorian

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

10.0 out of 10, Exceptional, (16)
"Clean, quiet and comfy. Ideal location in the countryside while visiting family"
The price is AU$250
includes taxes & fees
17 Mar - 18 Mar
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Turkey Trot At Heron Hill Retreat Hot Tub On Lake!

8.8 out of 10, Excellent, (12)
"The place was clean and I thoroughly enjoyed the fire pit and hot tub. It was unclear in the listing that this was connected to another unit and I was glad that it was not rented at the time of our stay. There was construction happening the first two days of our stay, but as we were prepping for my best friend's wedding, it wasn't really an issue. The construction crew was super nice. If I was ever planning a getaway in that area on the future, I would definitely consider this place again,...
Turkey Trot At Heron Hill Retreat Hot Tub On Lake!

The Lakeside Cottage in Stow!

9.6 out of 10, Exceptional, (52)
"The house was everything we needed to visit our son (a student at Kent) and celebrate Thanksgiving together. Toasty cottage with great wildlife watching - ducks, geese and groundhogs close to everything, including great hiking at The Ledges."
The Lakeside Cottage in Stow!

White Tail Run & Eagles Nest At Heron Hill Retreat 2 Hot Tubs On Lake!

10.0 out of 10, Exceptional, (2)
"As advertised, well equipped "
The price is AU$1,839
includes taxes & fees
23 Feb - 24 Feb
White Tail Run & Eagles Nest At Heron Hill Retreat 2 Hot Tubs On Lake!

Fully stocked Suite Dwntown Cuy falls! near cvnp and blossom. Sleeps 4

9.6 out of 10, Exceptional, (28)
"Small but cozy! "
The price is AU$381
includes taxes & fees
19 Feb - 20 Feb
Fully stocked Suite Dwntown Cuy falls! near cvnp and blossom. Sleeps 4

Spacious 4 Bedroom Sleeps 10 W/ Sauna and Hot Tub

Spacious 4 Bedroom Sleeps 10 W/ Sauna and Hot Tub

4 Bedroom/2 bath Cozy Lake Milton Getaway with dock. 300 yards to the water!

9.8 out of 10, Exceptional, (26)
"This property was perfect for our family needs during Christmas. With 3 small children in tow and meeting with grandparents, who also live out of town, this was the perfect fit for our needs. The host was great in communication and even went above and beyond to decorate for Christmas. It was great to be near both of our families."
4 Bedroom/2 bath Cozy Lake Milton Getaway with dock. 300 yards to the water!

Primitive cabin with additional camping room

9.8 out of 10, Exceptional, (12)
"We thoroghly enjoyed our stay. It was such a sweet getaway "
The price is AU$207
includes taxes & fees
19 Mar - 20 Mar
Primitive cabin with additional camping room

Remodeled Stow Home near Blossom Music Center/BMBW Ski Resort/Downtown Cuy Falls

9.8 out of 10, Exceptional, (20)
"Very clean! Easy to check in and out. Has everything we needed! Very nice!"
Remodeled Stow Home near Blossom Music Center/BMBW Ski Resort/Downtown Cuy Falls

Little house on the farm

10.0 out of 10, Exceptional, (90)
"We stayed in town for our daughter's wedding, now mind you we did not spend a lot of time at the house we still enjoyed our stay! It was very clean, and inviting and if we are ever in that area again we would definitely try and book again :)"
Little house on the farm

Barcade and rope swing bar, 5 minutes from The Avalon Grand Resort and Golf!

9.8 out of 10, Exceptional, (20)
"Fun couple nights. Good property. Easy in, easy out. Good times."
Barcade and rope swing bar, 5 minutes from The Avalon Grand Resort and Golf!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Windham you may be interested in

The Grand Resort

4.0 star property
9.4 out of 10, Exceptional, (703)
"Nice property , professional staff , and nice amenities. "
The price is AU$513
includes taxes & fees
24 Feb - 25 Feb
The Grand Resort

Kent State University Hotel and Conference Center

3.5 star property
9.4 out of 10, Exceptional, (1005)
"Great place to stay everyone was nice and friendly "
The price is AU$229
includes taxes & fees
23 Feb - 24 Feb
Kent State University Hotel and Conference Center

Comfort Inn & Suites Cuyahoga Falls - Akron

3.0 star property
8.4 out of 10, Very good, (1002)
"The management moved us daily during our stay. This was very inconvenient. "
The price is AU$154
includes taxes & fees
2 Mar - 3 Mar
Comfort Inn & Suites Cuyahoga Falls - Akron
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windham has to offer?

Conveniently located 2 bedroom home only minutes from hiking and state park fun!: This holiday home rental outside of Windham offers a fireplace, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Windham?

While exploring the area, visit family-friendly sights like AAA I-76 Antique Mall, or get outside and enjoy nature at Nelson Ledges Quarry Park. Nelson-Kennedy Ledges State Park and Hiram College are a couple of places you'll find in the wider area.

What’s a holiday rental in Windham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windham. Holiday rentals feature extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.