Streetsboro Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Streetsboro holiday rentals

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$6,964
HK$13,409 total
includes taxes & fees
30 Dec - 31 Dec
White Tail Run & Eagles Nest At Heron Hill Retreat 2 Hot Tubs On Lake!
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$4,082
HK$9,105 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mighty Duck & Black Bear 2 Hot Tubs On Lake At Heron Hill!
Outdoor spa tub
Black Bear At Heron Hill Retreat Hot Tub On Lake!

Black Bear At Heron Hill Retreat Hot Tub On Lake!

Black Bear At Heron Hill Retreat Hot Tub On Lake!
Streetsboro
9.6 out of 10, Exceptional, (4)
"This is an awesome rental, very spacious, clean and modern in a country setting close to the city."
United States
Paul D.
The price is HK$2,441
HK$4,976 total
includes taxes & fees
28 Dec - 29 Dec
Black Bear At Heron Hill Retreat Hot Tub On Lake!
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$5,871
HK$9,864 total
includes taxes & fees
30 Dec - 31 Dec
White Tail Run At Heron Hill Retreat Hot Tub Lake!
Interior
Primitive cabin with additional camping room

Primitive cabin with additional camping room

Primitive cabin with additional camping room
Atwater
9.8 out of 10, Exceptional, (15)
"Very clean very cozy host was terrific"
United States
Kevin G.
The price is HK$459
HK$841 total
includes taxes & fees
26 Dec - 27 Dec
Primitive cabin with additional camping room
Private kitchen
Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (3)
"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$700
HK$1,484 total
includes taxes & fees
27 Dec - 28 Dec
Peaceful private apartment in the charming Hiram countryside
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

Cozy, comfortable and close to Cleveland-Canton-Skiing & Cuyahoga Natl. Park
Akron
10.0 out of 10, Exceptional, (16)
"Adorable place! Host communication was great. Will stay again!!"
United States
Amanda V.
The price is HK$770
HK$1,532 total
includes taxes & fees
28 Dec - 29 Dec
Cozy, comfortable and close to Cleveland-Canton-Skiing & Cuyahoga Natl. Park
Dining
Charming & Updated ~ Long-Stays OK ~ Near Cleveland Clinic

Charming & Updated ~ Long-Stays OK ~ Near Cleveland Clinic

Charming & Updated ~ Long-Stays OK ~ Near Cleveland Clinic
Shaker Heights
9.4 out of 10, Exceptional, (8)
"We enjoyed our stay thanks so much."
United States
Jody T.
Charming & Updated ~ Long-Stays OK ~ Near Cleveland Clinic
Exterior detail
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Buckeye-Shaker
9.8 out of 10, Exceptional, (58)
"Great location. Host was very responsive. This unit is comfortable, well stocked and was perfect for our trip to Cleveland Clinic!"
United States
Anonymous traveller
The price is HK$560
HK$1,238 total
includes taxes & fees
30 Dec - 31 Dec
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Outdoor dining
Valley Overlook - Cozy 2BR Cabin near Blossom Music Center - Peninsula, Ohio

Valley Overlook - Cozy 2BR Cabin near Blossom Music Center - Peninsula, Ohio

Valley Overlook - Cozy 2BR Cabin near Blossom Music Center - Peninsula, Ohio
Akron
10.0 out of 10, Exceptional, (42)
"Gorgeous, quiet location and clean, comfy accommodations. "
United States
Michelle M.
The price is HK$925
HK$1,652 total
includes taxes & fees
18 Jan - 19 Jan 2026
Valley Overlook - Cozy 2BR Cabin near Blossom Music Center - Peninsula, Ohio
Fridge, microwave, oven, stovetop
Modern & Comfy ~ Close to Cleveland Clinic ~ Long-Stays Welcome ~ Safe Area

Modern & Comfy ~ Close to Cleveland Clinic ~ Long-Stays Welcome ~ Safe Area

Modern & Comfy ~ Close to Cleveland Clinic ~ Long-Stays Welcome ~ Safe Area
Shaker Heights
10.0 out of 10, Exceptional, (3)
"We were two adult couples and this was perfect for our needs. It has a big, beautiful kitchen and everything is up-to-date and freshly renovated. Quiet neighborhood, comfortable beds and a nice living room perfect for watching television or just relaxing with a book. Very spacious rooms! I'd certainly stay here again should I have a need of rooms in the area."
United States
Jean A.
The price is HK$732
HK$1,550 total
includes taxes & fees
27 Dec - 28 Dec
Modern & Comfy ~ Close to Cleveland Clinic ~ Long-Stays Welcome ~ Safe Area
Interior
Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe

Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe

Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe
Shaker Heights
9.8 out of 10, Exceptional, (7)
"Clean, Unique, Safe/Quiet "
United States
Will P.
The price is HK$781
HK$1,625 total
includes taxes & fees
3 Jan - 4 Jan 2026
Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe
Dining
Acadia Farms Carriage House

Acadia Farms Carriage House

Acadia Farms Carriage House
Northfield
10.0 out of 10, Exceptional, (1)
"The Carriage House was very clean, and has everything you need in a small floorplan. And the location was perfect for our plans. We came up to hike the Cuyahoga Valley park, and to go to the Rock & Roll hall of fame. "
United States
Jeff S.
The price is HK$898
HK$1,528 total
includes taxes & fees
15 Jan - 16 Jan 2026
Acadia Farms Carriage House
Oven
Cozy 1 Bedroom in Highland Square, pets welcome!!

Cozy 1 Bedroom in Highland Square, pets welcome!!

Cozy 1 Bedroom in Highland Square, pets welcome!!
Highland Square
9.0 out of 10, Wonderful, (48)
"Excellent value, pleasant neighborhood close to dining options."
United States
John
The price is HK$560
HK$754 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy 1 Bedroom in Highland Square, pets welcome!!
Dining
Cozy, Convenient Getaway 3Bd2Ba dog-friendly home in wonderful Akron, OH

Cozy, Convenient Getaway 3Bd2Ba dog-friendly home in wonderful Akron, OH

Cozy, Convenient Getaway 3Bd2Ba dog-friendly home in wonderful Akron, OH
North Hill
8.8 out of 10, Excellent, (16)
"Convenient location, lots of space, friendly and attentive host! Would definitely recommend!"
United States
Tamera J.
The price is HK$532
HK$2,355 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy, Convenient Getaway 3Bd2Ba dog-friendly home in wonderful Akron, OH
Smart TV
Comfy 3 Bedroom Entire Home With Cozy Vibes

Comfy 3 Bedroom Entire Home With Cozy Vibes

Comfy 3 Bedroom Entire Home With Cozy Vibes
South Akron
7.6 out of 10, Good, (4)
"Will message owner direct-good value, great location!"
United States
Jerome L.
The price is HK$490
HK$1,455 total
includes taxes & fees
26 Dec - 27 Dec
Comfy 3 Bedroom Entire Home With Cozy Vibes
TV
Close to Downtown | Near Museum | Little Italy

Close to Downtown | Near Museum | Little Italy

Close to Downtown | Near Museum | Little Italy
2.0 star property
Buckeye-Shaker
The price is HK$536
HK$1,490 total
includes taxes & fees
29 Dec - 30 Dec
Close to Downtown | Near Museum | Little Italy
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, (50)
"Room was spotless, everything perfect"
United States
Marla
The price is HK$665
HK$1,054 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Smart TV, books
Shaker Square|Sleeps 4|Front Porch|Coffee Station

Shaker Square|Sleeps 4|Front Porch|Coffee Station

Shaker Square|Sleeps 4|Front Porch|Coffee Station
Buckeye-Shaker
10.0 out of 10, Exceptional, (4)
"It is a clean, well maintained property. It was very comfortable & it is in a nice neighborhood."
United States
Julie S.
The price is HK$633
HK$2,347 total
includes taxes & fees
29 Dec - 30 Dec
Shaker Square|Sleeps 4|Front Porch|Coffee Station
Terrace/patio
Comfort Awaits at Cozy Get Away - Dog Friendly - 3BD / 2BA + Living Spaces

Comfort Awaits at Cozy Get Away - Dog Friendly - 3BD / 2BA + Living Spaces

Comfort Awaits at Cozy Get Away - Dog Friendly - 3BD / 2BA + Living Spaces
Ellet
9.4 out of 10, Exceptional, (10)
"Great house. Stocked with all of the necessities!"
United States
James S.
The price is HK$591
HK$2,421 total
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Awaits at Cozy Get Away - Dog Friendly - 3BD / 2BA + Living Spaces
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 Streetsboro Hotel Reviews

Comfort Inn & Suites Streetsboro - Kent

Comfort Inn & Suites Streetsboro - Kent

10/10 Excellent
"Great Staff thank you!"
Gervase 1-night trip
Posted 2 days ago
Comfort Inn & Suites Streetsboro - Kent

Find out more about Streetsboro

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

  • View our selection of featured holiday rentals in Streetsboro
  • Use the map to find apartments and other holiday homes in the Streetsboro neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Streetsboro while they last

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

Frequently asked questions

Are there holiday rentals in Streetsboro?

Yes, there are holiday rentals in Streetsboro close to ZipCity, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Streetsboro. While you're here, grab a bite or have a drink at the coffee shops.

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

Mighty Duck & Black Bear 2 Hot Tubs On Lake At Heron Hill!: This highly rated holiday home rental in Streetsboro is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Streetsboro?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Streetsboro stay.

What’s there to see and do in Streetsboro?

Cuyahoga River and Streetsboro City Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include ZipCity. While here, Boulder Creek Golf Club and Lake Rockwell are other places worth a visit.

What’s a holiday rental in Streetsboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Streetsboro. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for small groups.