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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Oakwood Village vacation rentals

A two-story house with a porch, a small front yard, and a visible front door.

1. 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.
$228 nightly
The price is $241
Oct 12 - Oct 13
Total with taxes and fees
Walk to Dining, Bars & Transit!
A modern living room with a flat-screen TV mounted on a wall, a wooden entertainment center, and a zebra-patterned rug.

2. 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
Chic Coventry — Enjoy 10% off 2+ Nights +Late Check Out
A modern living room with a flat-screen TV, a ceiling fan, and a kitchen area with a sink.

3. Contemporary Coventry

Contemporary Coventry
Cleveland
8.8 out of 10, Excellent, (60 reviews)
"Location was perfect. "
United States
Brian S.
$177 nightly
The price is $177
Oct 12 - Oct 13
Total with taxes and fees
Contemporary Coventry
A sign for Cleveland Metroparks at Edgewater Beach.

4. 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)
"It was perfect for an overnight trip to the city to see a concert."
United States
Laura F.
$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 wooden deck with a metal railing overlooking a forest.

5. 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, (63 reviews)
"The cabin was very nice and the area was very quiet, perfect for our biking adventure!"
United States
Kevin W.
$185 nightly
The price is $210
Oct 20 - Oct 21
Total with taxes and fees
Valley Overlook - Cozy Cabin near Blossom Music Center, 1BR - Peninsula, Ohio
A dining area with a dark wooden table and chairs, a chandelier, and a kitchen in the background.

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

Next 2 Christmas Story House/Tremont/5min downtown
Tremont
9.6 out of 10, Exceptional, (98 reviews)
"Host was great"
United States
Jennifer E.
$150 nightly
The price is $155
Oct 15 - Oct 16
Total with taxes and fees
Next 2 Christmas Story House/Tremont/5min downtown
A modern bedroom with a loft bed, a sofa, and a coffee table.

7. Modern Victorian Studio -Steps to Cleveland Clinic

Modern Victorian Studio -Steps to Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (19 reviews)
"Great location near Cleveland Clinic. Very clean room with free parking onsite."
United States
Mike
$212 nightly
The price is $230
Oct 25 - Oct 26
Total with taxes and fees
Modern Victorian Studio -Steps to Cleveland Clinic
A modern living room with a grey sectional sofa, a red chair, a round wooden coffee table, a TV stand, and a large window with a city view.

8. Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.

Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.
Downtown Cleveland
9.2 out of 10, Wonderful, (20 reviews)
"Great stay would recommend to anyone"
United States
Shane S.
$192 nightly
The price is $198
Oct 13 - Oct 14
Total with taxes and fees
Cleveland Loft-Wolstein/Progressive/Playhouse/CSU.
A living room with a sofa, a coffee table, a fireplace, and artwork on the wall.

9. 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.
$213 nightly
The price is $213
Oct 12 - Oct 13
Total with taxes and fees
The Gallery House - Art curated by local artist!
A modern living room with a blue sofa, a coffee table, and a kitchen area with a bar and stools.

10. 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.
$207 nightly
The price is $224
Oct 13 - Oct 14
Total with taxes and fees
Upscale Little Italy 2BR | Private Drive & Patio
A wooden cabin with a large dining table and benches, surrounded by large windows offering a view of the forest.

11. 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 13 - Oct 14
Total with taxes and fees
Pine Lake Trout Club Cabin #8!!!
A bright kitchen with white cabinets, a wooden dining table, and chairs.

12. Luxury Downtown Townhome w/ Private Garage Unit 10

Luxury Downtown Townhome w/ Private Garage Unit 10
Downtown Cleveland
9.4 out of 10, Exceptional, (38 reviews)
"Property was very clean and super close to the auditorium."
United States
Paula
$171 nightly
The price is $185
Oct 19 - Oct 20
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 10
A dining area with a wooden table and chairs, a bench, and a view of the outdoors through large windows.

13. Luxury Downtown Townhome w/ Private Garage Unit 14

Luxury Downtown Townhome w/ Private Garage Unit 14
Downtown Cleveland
9.6 out of 10, Exceptional, (54 reviews)
"It was Everything I was expecting.!!!!!!Great stay!!"
United States
sara r.
$150 nightly
The price is $162
Oct 12 - Oct 13
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 14
A covered patio area with wooden beams, a swing chair, and several plastic chairs.

14. Gordon Square Studio ~ 4 Mi to Downtown Cleveland!

Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
3.0 star property
Detroit - Shoreway
8.8 out of 10, Excellent, (8 reviews)
"Lovely stay - comfortable studio, communicative host, great location, and easy parking. "
United States
Rachel
Gordon Square Studio ~ 4 Mi to Downtown Cleveland!
A two-door entrance with a concrete step leading up to it, flanked by a large green bush and a stone wall.

15. Luxury Downtown Townhome w/ Private Garage Unit 7

Luxury Downtown Townhome w/ Private Garage Unit 7
Downtown Cleveland
9.8 out of 10, Exceptional, (35 reviews)
"Emails were very informative and the place was clean and well managed! Was nice to have the garage and not have to pay for parking! Would stay here again if we visit Cleveland again!"
United States
Michelle
$160 nightly
The price is $173
Oct 15 - Oct 16
Total with taxes and fees
Luxury Downtown Townhome w/ Private Garage Unit 7
Kitchen area.

16. 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, (41 reviews)
"Super clean, decor was great. Nice sized fridge, plenty of places to sit and converse with my wife. Lots of room outside to roam and has a great fire pit. Close to anything you might need and a very good host. We will return and I've already turned a coworker onto it."
United States
Baron
$125 nightly
The price is $125
Oct 19 - Oct 20
Total with taxes and fees
1-bed on 1 acre complete remodel. Cabin like interior...unique. Sleeps 2.
A hotel room with a large window offering a view of a cityscape, a bed, a nightstand, and a lamp.

17. Peaceful & Relaxing 2BR | Cleveland Clinic

Peaceful & Relaxing 2BR | Cleveland Clinic
University Circle
9.8 out of 10, Exceptional, (8 reviews)
"The condo was extremely clean and perfect for our needs! Will definitely stay again if it's available."
United States
Michelle G.
$237 nightly
The price is $257
Oct 12 - Oct 13
Total with taxes and fees
Peaceful & Relaxing 2BR | Cleveland Clinic
A dining area with a wooden table and chairs, a chandelier, and a television on a shelf.

18. Upscale suite in Lakewood

Upscale suite in Lakewood
Lakewood
9.6 out of 10, Exceptional, (14 reviews)
"Good location"
United States
Ronald
$150 nightly
The price is $155
Oct 15 - Oct 16
Total with taxes and fees
Upscale suite in Lakewood
A modern living room with leather sofas, a coffee table, and a flat-screen TV mounted on the wall.

19. Akron OH|2 Full Bed Non Smoking

Akron OH|2 Full Bed Non Smoking
Akron OH
10.0 out of 10, Exceptional, (69 reviews)
"Cozy atmosphere and friendly staff made our stay enjoyable."
United States
Anonymous traveler
$75 nightly
The price is $84
Oct 13 - Oct 14
Total with taxes and fees
Akron OH|2 Full Bed Non Smoking
A modern kitchen with white cabinets, a coffee maker, and a chalkboard wall with writing.

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

Cozy 1 Bedroom in Highland Square, pets welcome!!
Highland Square
9.0 out of 10, Wonderful, (66 reviews)
"Loved our stay! Comfortable, clean and restful. Very welcoming to pets. Easy"
United States
Ruth B.
$103 nightly
The price is $103
Oct 12 - Oct 13
Total with taxes and fees
Cozy 1 Bedroom in Highland Square, pets welcome!!
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

Extended Stay America Premier Suites - Cleveland - Independence

Extended Stay America Premier Suites - Cleveland - Independence

8/10 Good
"It was “ok”."
LaShelle 2-night trip
Posted 2 hours ago
Extended Stay America Premier Suites - Cleveland - Independence

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 $73 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.