Windham Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Windham holiday rentals

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!
Warren
10.0 out of 10, Exceptional, (130 reviews)
"Great stay and pet friendly. Very clean and excellent, comfortable furniture. Definitely would stay again when in the area"
United States
Andrew B.
The price is HK$705
HK$1,348 total
includes taxes & fees
12 May - 13 May
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
View from property

Prairie House RV Spaces

Prairie House RV Spaces
1.0 star property
Deerfield
8.0 out of 10, Very good, (2 reviews)
"Relax a little close to road but easy in easy out. "
United States
Mark
The price is HK$330
HK$353 total
includes taxes & fees
8 May - 9 May
Prairie House RV Spaces
Fridge, microwave, oven, stovetop

Cozy, comfortable and close to Cleveland-Canton-Skiing & Cuyahoga Natl. Park

Cozy, comfortable and close to Cleveland-Canton-Skiing & Cuyahoga Natl. Park
Akron
10.0 out of 10, Exceptional, (18 reviews)
"Adorable place! Host communication was great. Will stay again!!"
United States
Amanda V.
The price is HK$862
HK$1,653 total
includes taxes & fees
19 May - 20 May
Cozy, comfortable and close to Cleveland-Canton-Skiing & Cuyahoga Natl. Park
Interior

Buckeye Bungalow-Charming 2-bedroom apartment in Youngstown

Buckeye Bungalow-Charming 2-bedroom apartment in Youngstown
Youngstown
10.0 out of 10, Exceptional, (5 reviews)
"The stay was amazing! Only thing missing was extra linens in case of emergency. "
United States
June D.
The price is HK$737
HK$1,168 total
includes taxes & fees
8 May - 9 May
Buckeye Bungalow-Charming 2-bedroom apartment in Youngstown
Exterior

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (96 reviews)
"Wonderful hosts, made us feel right at home!"
United States
Lynn
The price is HK$1,214
HK$1,794 total
includes taxes & fees
11 May - 12 May
Little house on the farm
Terrace/patio

Lakeside Paradise on Berlin

Lakeside Paradise on Berlin
Deerfield
9.8 out of 10, Exceptional, (103 reviews)
"Nice stay, kids had a great time and want to return."
United States
Joey H.
The price is HK$1,528
HK$2,524 total
includes taxes & fees
10 May - 11 May
Lakeside Paradise on Berlin
Property grounds

2 bedroom apartment in the beautiful Middlefield countryside!

2 bedroom apartment in the beautiful Middlefield countryside!
Middlefield
The price is HK$784
HK$1,450 total
includes taxes & fees
12 May - 13 May
2 bedroom apartment in the beautiful Middlefield countryside!
Exterior

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, (60 reviews)
"We loved this little place. "
United States
Rolanda R.
The price is HK$846
HK$1,277 total
includes taxes & fees
13 May - 14 May
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Dining

Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
8.8 out of 10, Excellent, (12 reviews)
"I always love staying here! "
United States
Jade R.
The price is HK$1,332
HK$1,528 total
includes taxes & fees
12 May - 13 May
Pine Lake Trout Club Cabin #8!!!
Private kitchen

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful experience! The bed was very comfortable and the space was beautiful and clean. We enjoyed how quiet the area was and it was perfect for our weekend getaway. We will absolutely be staying here the next time we are out this way!"
United States
Ashley
The price is HK$705
HK$1,479 total
includes taxes & fees
8 May - 9 May
Peaceful private apartment in the charming Hiram countryside
Dining

Rest, Relax and Enjoy our Gentleman's Farm in Mantua

Rest, Relax and Enjoy our Gentleman's Farm in Mantua
Mantua
9.6 out of 10, Exceptional, (38 reviews)
"We had a great time here! The kitchen was well-stocked and we enjoyed the beautiful outdoor gardens! We would definitely come back again!"
United States
Dale D.
The price is HK$1,003
HK$2,045 total
includes taxes & fees
11 May - 12 May
Rest, Relax and Enjoy our Gentleman's Farm in Mantua
Fridge, microwave, oven, stovetop

Luxury Home near Blossom, CVNP, Ski Resort

Luxury Home near Blossom, CVNP, Ski Resort
Cuyahoga Falls
10.0 out of 10, Exceptional, (6 reviews)
"Nice house, very clean, great location."
United States
David R.
The price is HK$875
HK$1,870 total
includes taxes & fees
10 May - 11 May
Luxury Home near Blossom, CVNP, Ski Resort
Interior

Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful place and very well taken care of."
United States
Andrew G.
The price is HK$1,175
HK$1,614 total
includes taxes & fees
8 May - 9 May
Nestled Inn Mespo Modern & Cozy Apartment
Exterior

Relaxing Retreat Near Cleveland | Shared Indoor Pool + BBQ Area

Relaxing Retreat Near Cleveland | Shared Indoor Pool + BBQ Area
Stow
The price is HK$995
HK$1,301 total
includes taxes & fees
17 May - 18 May
Relaxing Retreat Near Cleveland | Shared Indoor Pool + BBQ Area
Private kitchen

Lovely private 3 bedroom house nestled in the Hiram countryside.

Lovely private 3 bedroom house nestled in the Hiram countryside.
Garrettsville
9.0 out of 10, Wonderful, (9 reviews)
"Clean, large and quiet place."
United States
Michelle T.
The price is HK$1,450
HK$2,748 total
includes taxes & fees
10 May - 11 May
Lovely private 3 bedroom house nestled in the Hiram countryside.
Smart TV

Private Studio unit

Private Studio unit
Warren
8.8 out of 10, Excellent, (5 reviews)
"Great hospitality and the amenities were spot on. Perfect set up if you’re looking for something for a few days."
United States
Wendie P.
The price is HK$407
HK$838 total
includes taxes & fees
11 May - 12 May
Private Studio unit
Exterior

Modern Retreat Near Cuyahoga Valley Bright & Spacious

Modern Retreat Near Cuyahoga Valley Bright & Spacious
Hudson
9.0 out of 10, Wonderful, (2 reviews)
"Very clean home, fantastic option for stays in the Hudson OH area. Very close to downtown Hudson shops and restaurants. Very comfortable stay, I will be back. Communication with owners was outstanding!"
United States
Jim H.
Modern Retreat Near Cuyahoga Valley Bright & Spacious
Microwave, oven, stovetop

Private house 1 bedroom 1 bath ground-floor

Private house 1 bedroom 1 bath ground-floor
Warren
10.0 out of 10, Exceptional, (1 review)
"Everything was amazing...the property was as described. The host and property manager were very approachable and responded quickly when needed. Fanny, the property manager is a treasure! We felt very comfortable and safe. Would definitely stay here again. The only thing I'd say would be to provide a light for the backyard area. Thank you so much for being exceptional hosts!Kathy & Mark "
United States
KATHLEEN W.
The price is HK$572
HK$1,081 total
includes taxes & fees
21 May - 22 May
Private house 1 bedroom 1 bath ground-floor
Exterior

2 Bedroom | Comfortable Suite Near Cleveland

2 Bedroom | Comfortable Suite Near Cleveland
Stow
The price is HK$1,530
HK$1,979 total
includes taxes & fees
10 May - 11 May
2 Bedroom | Comfortable Suite Near Cleveland
Dining

Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (72 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
The price is HK$1,559
HK$2,727 total
includes taxes & fees
11 May - 12 May
Country Cottage Farm Stay at Stoneycreek Acres
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

Super 8 by Wyndham Kent/Akron Area

Super 8 by Wyndham Kent/Akron Area

8/10 Good
"We were short on towels and toilet paper. The door key did not work at first . I had to make a few trips downstairs to get what we needed. Over all it was clean and beds were good . Just check what you need before you get stated. We had 3 people registered for the room and only two sets of towles"
Beulah 1-night trip
Posted 1 hour ago
Super 8 by Wyndham Kent/Akron Area

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?

Lakefront Haven w/ 50-ft Dock 4BR Near Punderson Park & Amish Country EV Charger: This holiday home rental outside of Windham offers a balcony, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, 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 Southington Township Park 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.