Windham Holiday Rentals

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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Windham holiday rentals

Exterior
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Burton
10.0 out of 10, Exceptional, (49)
"Room was spotless, everything perfect"
United States
Marla
The price is HK$700
HK$1,089 total
includes taxes & fees
22 Dec - 23 Dec
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Smart TV
Lakeside living awaits at beautiful Lake Milton, OH with dock across the street

Lakeside living awaits at beautiful Lake Milton, OH with dock across the street

Lakeside living awaits at beautiful Lake Milton, OH with dock across the street
Lake Milton
10.0 out of 10, Exceptional, (155)
"Amazing stay !! Hope to return "
United States
Lisa J.
Lakeside living awaits at beautiful Lake Milton, OH with dock across the street
Smart TV, fireplace
Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country

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

Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country
Burton
9.8 out of 10, Exceptional, (29)
"Wonderful property and house for our family of 22 to enjoy for the week! Great pool and so many different gathering spaces for our family to use, from age 6-74, all were very pleased! The house was clean and very well stocked…Nathan and JT were so responsive and helpful throughout the week…looking forward to a return visit! "
United States
Clifton P.
Cheerful Family Manor- Sleeps 25 w/hot tub and private pool in Amish Country
View from property
Prairie House RV Spaces

Prairie House RV Spaces

Prairie House RV Spaces
1.0 star property
Deerfield
8.0 out of 10, Very good, (1)
"Relax a little close to road but easy in easy out. "
United States
Mark
The price is HK$327
HK$350 total
includes taxes & fees
22 Dec - 23 Dec
Prairie House RV Spaces
Interior
3 blocks from the falls viewing area in the heart of downtown Chagrin Falls!

3 blocks from the falls viewing area in the heart of downtown Chagrin Falls!

3 blocks from the falls viewing area in the heart of downtown Chagrin Falls!
Chagrin Falls
10.0 out of 10, Exceptional, (25)
"Nice little house super close to downtown Very clean and host was super responsive Would stay here again"
United States
Carrie C.
3 blocks from the falls viewing area in the heart of downtown Chagrin Falls!
Interior
White Tail Run & Eagles Nest At Heron Hill Retreat 2 Hot Tubs On Lake!

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

White Tail Run & Eagles Nest At Heron Hill Retreat 2 Hot Tubs On Lake!
Streetsboro
10.0 out of 10, Exceptional, (3)
"Overall our family enjoyed being able to spread out and also enjoy the beautiful scenery! Snow and cold kept us inside for most of the time, but it was very peaceful."
United States
Leslie S.
The price is HK$9,459
HK$16,367 total
includes taxes & fees
30 Dec - 31 Dec
White Tail Run & Eagles Nest At Heron Hill Retreat 2 Hot Tubs On Lake!
Terrace/patio
Lakeside Paradise on Berlin

Lakeside Paradise on Berlin

Lakeside Paradise on Berlin
Deerfield
9.8 out of 10, Exceptional, (103)
"Nice stay, kids had a great time and want to return."
United States
Joey H.
The price is HK$1,517
HK$2,514 total
includes taxes & fees
21 Dec - 22 Dec
Lakeside Paradise on Berlin
Exterior
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Burton
10.0 out of 10, Exceptional, (4)
"Axel was very accommodating and helpful. The property is great."
United States
Jeremy M.
The price is HK$2,451
HK$2,785 total
includes taxes & fees
20 Dec - 21 Dec
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Outdoor spa tub
Mighty Duck & Black Bear 2 Hot Tubs On Lake At Heron Hill!

Mighty Duck & Black Bear 2 Hot Tubs On Lake At Heron Hill!

Mighty Duck & Black Bear 2 Hot Tubs On Lake At Heron Hill!
Streetsboro
10.0 out of 10, Exceptional, (1)
"Worked great for our needs! Very comfortable and housed everyone with room to spare."
United States
Jamie L.
The price is HK$4,084
HK$9,110 total
includes taxes & fees
11 Jan - 12 Jan 2026
Mighty Duck & Black Bear 2 Hot Tubs On Lake At Heron Hill!
Exterior
The Wildflower - Private cabin in wooded setting

The Wildflower - Private cabin in wooded setting

The Wildflower - Private cabin in wooded setting
Middlefield
10.0 out of 10, Exceptional, (42)
"Wonderful relaxing getaway. Looking forward to coming back sometime!"
United States
Ryan F.
The Wildflower - Private cabin in wooded setting
Fridge, microwave, oven, stovetop
The Lakeside Cottage in Stow!

The Lakeside Cottage in Stow!

The Lakeside Cottage in Stow!
Stow
9.8 out of 10, Exceptional, (87)
"We really enjoyed our time- thank you! "
United States
Adele I.
The Lakeside Cottage in Stow!
1 bedroom, free WiFi, bed sheets
Ledgestone Farms-Rustic Western Getaway

Ledgestone Farms-Rustic Western Getaway

Ledgestone Farms-Rustic Western Getaway
Warren
8.6 out of 10, Excellent, (29)
"Clean pleasant and quiet atmosphere "
United States
Christine P.
The price is HK$778
HK$1,323 total
includes taxes & fees
20 Dec - 21 Dec
Ledgestone Farms-Rustic Western Getaway
Terrace/patio
White Tail Run At Heron Hill Retreat Hot Tub Lake!

White Tail Run At Heron Hill Retreat Hot Tub Lake!

White Tail Run At Heron Hill Retreat Hot Tub Lake!
Streetsboro
10.0 out of 10, Exceptional, (8)
"Great place for a bunch of people!"
United States
Jamie L.
The price is HK$6,724
HK$10,862 total
includes taxes & fees
30 Dec - 31 Dec
White Tail Run At Heron Hill Retreat Hot Tub Lake!
Fridge, microwave, oven, stovetop
Holidays at Lake Time Cottage Lake Milton OH: Wifi, Smart TVs, fireplace

Holidays at Lake Time Cottage Lake Milton OH: Wifi, Smart TVs, fireplace

Holidays at Lake Time Cottage Lake Milton OH: Wifi, Smart TVs, fireplace
Lake Milton
10.0 out of 10, Exceptional, (29)
"Adorable property with a perfect kitchen and nice backyard setup. You can tell the owner cares about the property with all the little details to make your stay enjoyable. Lake Milton is a wonderful lake, and I hope to be back."
United States
Courtney S.
Holidays at Lake Time Cottage Lake Milton OH: Wifi, Smart TVs, fireplace
Property grounds
Eagles Nest At Heron Hill Retreat Hot Tub on Lake!

Eagles Nest At Heron Hill Retreat Hot Tub on Lake!

Eagles Nest At Heron Hill Retreat Hot Tub on Lake!
Streetsboro
9.6 out of 10, Exceptional, (15)
"The property easily accommodated my wife and I, our two dogs, and 3 of our adult children with their spouses for a long weekend visit. It was perfectly located near Cuyahoga Valley National Park."
United States
Mike W.
Eagles Nest At Heron Hill Retreat Hot Tub on Lake!
Smart TV, fireplace
Conveniently located 2 bedroom home only minutes from hiking and state park fun!

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

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Warren
10.0 out of 10, Exceptional, (126)
"Cute little house, perfect for a long weekend stay with the family "
United States
Megan M.
The price is HK$700
HK$1,323 total
includes taxes & fees
20 Dec - 21 Dec
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Blue Shutters Inn

Blue Shutters Inn

Blue Shutters Inn
Youngstown
9.8 out of 10, Exceptional, (26)
"Good place. "
United States
Earl Jamieson
The price is HK$739
HK$1,167 total
includes taxes & fees
28 Dec - 29 Dec
Blue Shutters Inn
Fridge, microwave, oven, stovetop
Oasis at Avalon Lakes - Hot Tub - Gas Fire Pit - Outdoor livingroom w/gas fire

Oasis at Avalon Lakes - Hot Tub - Gas Fire Pit - Outdoor livingroom w/gas fire

Oasis at Avalon Lakes - Hot Tub - Gas Fire Pit - Outdoor livingroom w/gas fire
Warren
10.0 out of 10, Exceptional, (31)
"Great!"
United States
Jennifer V.
Oasis at Avalon Lakes - Hot Tub - Gas Fire Pit - Outdoor livingroom w/gas fire
Property grounds
Sunset cottage complete w/large deck, fire pit and mins away from public beach

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

Sunset cottage complete w/large deck, fire pit and mins away from public beach
Lake Milton
9.2 out of 10, Wonderful, (71)
"Great place for the price! Our family truly enjoyed our stay. Maybe could use a new cleaning crew?"
United States
jklorenzen
Sunset cottage complete w/large deck, fire pit and mins away from public beach
Golf
Charming Lake cottage/duplex, Golf outing ready in beautiful Lake Milton.

Charming Lake cottage/duplex, Golf outing ready in beautiful Lake Milton.

Charming Lake cottage/duplex, Golf outing ready in beautiful Lake Milton.
Lake Milton
Charming Lake cottage/duplex, Golf outing ready in beautiful Lake Milton.
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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Top Windham Hotel Reviews

Kent State University Hotel and Conference Center

Kent State University Hotel and Conference Center

10/10 Excellent
"Super clean"
nallelyt 1-night trip
Posted 4 days ago
Kent State University Hotel and Conference Center

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
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  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

Look no further and take a look at our great range of rental properties in Windham!

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?

Lakeside living awaits at beautiful Lake Milton, OH with dock across the street: This holiday home rental outside of Windham is located on a lake, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.