A bridge over a calm river surrounded by dense green trees.

Oakwood Village Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Oakwood Village vacation rentals

A dining area with a round table, chairs, a clock on the wall, and a potted plant.

1. Acadia Farms Carriage House

Acadia Farms Carriage House
Northfield
9.6 out of 10, Exceptional, (14 reviews)
"Clean room, beautiful grounds, well equipped kitchen, great location for dog walks! Perfect for our family of four!"
United States
Natalie
$211 nightly
The price is $211
Oct 26 - Oct 27
Total with taxes and fees
Acadia Farms Carriage House
A two-story house with a porch, a small front yard, and a visible front door.

2. Walk to Dining, Bars & Transit!

Walk to Dining, Bars & Transit!
Union-Miles Park
8.4 out of 10, Very good, (146 reviews)
"We came for my son’s graduation and had a great time. The location was centralized to everything we wanted to do. We would stay again."
United States
Chrissy W.
$226 nightly
The price is $239
Oct 4 - Oct 5
Total with taxes and fees
Walk to Dining, Bars & Transit!
A wooden cabin with a large dining table and benches, surrounded by large windows offering a view of the forest.

3. Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
8.8 out of 10, Excellent, (15 reviews)
"I loved this place and will definitely be back in the fall. I have already booked another time in October. Very peaceful and tranquil. The cabin had everything anyone would need. Wonderful getaway."
United States
Jeff
$195 nightly
The price is $195
Oct 4 - Oct 5
Total with taxes and fees
Pine Lake Trout Club Cabin #8!!!
A modern kitchen with white cabinets, a coffee maker, and a chalkboard wall with writing.

4. Cozy 1 Bedroom in Highland Square, pets welcome!!

Cozy 1 Bedroom in Highland Square, pets welcome!!
Highland Square
9.0 out of 10, Wonderful, (64 reviews)
"Loved our stay! Comfortable, clean and restful. Very welcoming to pets. Easy"
United States
Ruth B.
$97 nightly
The price is $97
Oct 2 - Oct 3
Total with taxes and fees
Cozy 1 Bedroom in Highland Square, pets welcome!!
A bedroom with a bed, a flat-screen TV mounted on the wall, a closet with louvered doors, and a window with curtains.

5. Hilliard Lofts

Hilliard Lofts
2.0 star property
Downtown Cleveland
$225 nightly
The price is $264
Oct 4 - Oct 5
Total with taxes and fees
Hilliard Lofts
A modern bedroom with a loft bed, a sofa, and a coffee table.

6. Modern Victorian Studio -Steps to Cleveland Clinic

Modern Victorian Studio -Steps to Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (18 reviews)
"Great location near Cleveland Clinic. Very clean room with free parking onsite."
United States
Mike
$203 nightly
The price is $220
Oct 18 - Oct 19
Total with taxes and fees
Modern Victorian Studio -Steps to Cleveland Clinic
A living room with a sofa, a coffee table, a fireplace, and artwork on the wall.

7. The Gallery House - Art curated by local artist!

The Gallery House - Art curated by local artist!
Cleveland Heights
9.6 out of 10, Exceptional, (9 reviews)
"Everything was great. I will be back!"
United States
David T.
$197 nightly
The price is $197
Oct 25 - Oct 26
Total with taxes and fees
The Gallery House - Art curated by local artist!
Kitchen area.

8. 1-bed on 1 acre complete remodel. Cabin like interior...unique. Sleeps 2.

1-bed on 1 acre complete remodel. Cabin like interior...unique. Sleeps 2.
Strongsville
9.8 out of 10, Exceptional, (39 reviews)
"Great little place in a great location. Comfy and clean."
United States
Wendy L.
$134 nightly
The price is $134
Oct 2 - Oct 3
Total with taxes and fees
1-bed on 1 acre complete remodel. Cabin like interior...unique. Sleeps 2.
A modern living room with a flat-screen TV mounted on a wall, a wooden entertainment center, and a zebra-patterned rug.

9. Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out

Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
Cleveland Heights
9.0 out of 10, Wonderful, (27 reviews)
"Excellent walkable location. Good for one night in town for an event."
United States
Whitney
$171 nightly
The price is $173
Oct 4 - Oct 5
Total with taxes and fees
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
A wooden deck with a metal railing overlooking a forest.

10. Valley Overlook - Cozy Cabin near Blossom Music Center, 1BR - Peninsula, Ohio

Valley Overlook - Cozy Cabin near Blossom Music Center, 1BR - Peninsula, Ohio
Akron
9.8 out of 10, Exceptional, (62 reviews)
"Clean and easy to get in an out. Would recommend for travel to Cuyahoga NP."
United States
Richard M.
$188 nightly
The price is $213
Oct 7 - Oct 8
Total with taxes and fees
Valley Overlook - Cozy Cabin near Blossom Music Center, 1BR - Peninsula, Ohio
A modern living room with a blue sofa, a coffee table, and a kitchen area with a bar and stools.

11. Upscale Little Italy 2BR | Private Drive & Patio

Upscale Little Italy 2BR | Private Drive & Patio
University Circle
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Sandra S.
$206 nightly
The price is $223
Oct 4 - Oct 5
Total with taxes and fees
Upscale Little Italy 2BR | Private Drive & Patio
A Roku TV on a wooden TV stand with a potted plant beside it.

12. Cozy 1bed 1bath near Airport, Cleveland Clinic, & Downtown CLE

Cozy 1bed 1bath near Airport, Cleveland Clinic, & Downtown CLE
Clark-Fulton
9.2 out of 10, Wonderful, (5 reviews)
"Place looks a lot better in photos than in actuality but all in all WAY better than any hotel. The parking situation is a bit dicey though and the door to the bathroom can use an upgrade."
United States
Mohammad B.
$137 nightly
The price is $137
Oct 4 - Oct 5
Total with taxes and fees
Cozy 1bed 1bath near Airport, Cleveland Clinic, & Downtown CLE
A sign for Cleveland Metroparks at Edgewater Beach.

13. CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC

CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
Goodrich-Kirtland Park
8.6 out of 10, Excellent, (55 reviews)
"Everything as described! Great stay!"
United States
Billy M.
$138 nightly
The price is $138
Oct 26 - Oct 27
Total with taxes and fees
CAL KING BED, FREE PARKING PASS FOR 1 CAR, BY DOWNTOWN & CLINIC
A modern living room with a sofa, red chair, and a TV displaying 'NETFLIX'.

14. Rock & Roll Flat w/ Indoor Pool+Sauna+Gym•Downtown

Rock & Roll Flat w/ Indoor Pool+Sauna+Gym•Downtown
Downtown Cleveland
9.4 out of 10, Exceptional, (16 reviews)
"The place was clean and uncluttered. Bed was a little to soft and lumpy. Rooftop was very nice."
United States
Chun W.
$146 nightly
The price is $157
Oct 7 - Oct 8
Total with taxes and fees
Rock & Roll Flat w/ Indoor Pool+Sauna+Gym•Downtown

15. Little Italy Gem | King Bed, Gym & Free Parking

Little Italy Gem | King Bed, Gym & Free Parking
University Circle
9.6 out of 10, Exceptional, (5 reviews)
"Amazing place to stay"
United States
Anonymous traveler
$181 nightly
The price is $197
Oct 26 - Oct 27
Total with taxes and fees
Little Italy Gem | King Bed, Gym & Free Parking
A crowded beach with people swimming and walking along the shore, a large blue archway, and buildings in the background.

16. Historic century home in Parma -oh so charming

Historic century home in Parma -oh so charming
Parma
9.8 out of 10, Exceptional, (59 reviews)
"Great location - very quiet. House very clean. Owner very responsive. Will stay again. "
United States
Todd M.
$202 nightly
The price is $227
Oct 4 - Oct 5
Total with taxes and fees
Historic century home in Parma -oh so charming
A modern kitchen with a central island, stainless steel appliances, pendant lighting, and a wooden floor.

17. Charming studio apartment in fantastic Cleveland Tremont area

Charming studio apartment in fantastic Cleveland Tremont area
Tremont
7.8 out of 10, Good, (42 reviews)
"This is a great apartment for a quick trip."
United States
Kristin
$141 nightly
The price is $141
Oct 5 - Oct 6
Total with taxes and fees
Charming studio apartment in fantastic Cleveland Tremont area
A dining area with a dark wooden table, four chairs, and a decorative centerpiece.

18. Classic Meets Contemporary I Minutes to Cle Clinic

Classic Meets Contemporary I Minutes to Cle Clinic
Cleveland Heights
9.6 out of 10, Exceptional, (14 reviews)
"House was very clean and cozy. Great location."
United States
Monica
$213 nightly
The price is $213
Oct 4 - Oct 5
Total with taxes and fees
Classic Meets Contemporary I Minutes to Cle Clinic
A dining area with a dark wooden table and chairs, a chandelier, and a kitchen in the background.

19. Next 2 Christmas Story House/Tremont/5min downtown

Next 2 Christmas Story House/Tremont/5min downtown
Tremont
9.4 out of 10, Exceptional, (96 reviews)
"Host was great"
United States
Jennifer E.
$150 nightly
The price is $155
Oct 5 - Oct 6
Total with taxes and fees
Next 2 Christmas Story House/Tremont/5min downtown
A living room with a sofa, coffee table, and a TV.

20. The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (22 reviews)
"The house was great for a quick overnight stay and Billy was very responsive answering questions about the house and check-in process. The backyard was large and very accommodating for our two dogs. Would stay again!"
United States
Amy O.
$223 nightly
The price is $223
Oct 5 - Oct 6
Total with taxes and fees
The House Hotels - Superior Road
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 Oakwood Village Hotel Reviews

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

10/10 Excellent
"Nice"
Ashlyn 4-night trip
Posted 3 hours ago
Hotel Indigo Cleveland Downtown by IHG

Find out more about Oakwood Village

Everything you need to know about Oakwood Village vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakwood Village vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakwood Village vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakwood Village vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakwood Village. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oakwood Village in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $77 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakwood Village rentals

At Expedia, we put the best Oakwood Village vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oakwood Village rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakwood Village vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakwood Village. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Oakwood Village?

Yes, there are vacation rentals close to well known points of interest in Oakwood Village, or you can go with a more secluded option if you're looking for relaxation. Oakwood Village is known for its shopping and restaurants. Make sure you have time to check out the sporting events while you're in the area.

What are some of the best vacation home rentals in Oakwood Village?

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This vacation home rental near Oakwood Village offers a balcony, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Oakwood Village?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Oakwood Village stay.

What can I see and do in Oakwood Village?

Bedford Reservation and South Chagrin Reservation are a couple of lovely local spots to get outside and enjoy nature. MGM Northfield Park and Thistledown Racetrack are a couple of places you'll find in the larger area.

What are vacation rentals like in Oakwood Village?

Vacation rentals are privately owned properties you can stay in for several days or longer in Oakwood Village. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for small groups.