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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Oakland vacation rentals

A lush green landscape with a clear sky and fluffy clouds.

1. Relax & Refresh while enjoying the Simple Life of Amish Country - A Safe Haven

Relax & Refresh while enjoying the Simple Life of Amish Country - A Safe Haven
New Wilmington
10.0 out of 10, Exceptional, (76 reviews)
"The rental was a remodeled lower level of the house. It was very roomy, clean and comfortable with furnishings that were better than most rentals. The host was very friendly and accommodating during or stay. We look forward to returning the next time we stay in the area."
United States
Laurence J
The price is ￥23,545
￥39,260 total
includes taxes & fees
Oct 21 - Oct 22
Relax & Refresh while enjoying the Simple Life of Amish Country - A Safe Haven
A room with a wooden bench, a window with curtains, and a wooden cabinet.

2. Quiet home with old world charm to enjoy visiting relatives in New Castle, PA

Quiet home with old world charm to enjoy visiting relatives in New Castle, PA
New Castle
10.0 out of 10, Exceptional, (4 reviews)
"If you find yourself in New Castle, this home is the best place to stay. Beautiful home, excellent host, perfect accommodations."
United States
Leanne S.
The price is ￥22,191
￥37,630 total
includes taxes & fees
Nov 1 - Nov 2
Quiet home with old world charm to enjoy visiting relatives in New Castle, PA
A cozy living room with a stone fireplace, wooden ceiling, and a comfortable seating area with a sofa and chairs.

3. Nate`s Cabin at Water`s Edge

Nate`s Cabin at Water`s Edge
Portersville
10.0 out of 10, Exceptional, (19 reviews)
"It was a nice relaxing getaway close to home. The atmosphere was very quiet and peaceful. "
United States
Kristine M.
The price is ￥46,339
￥82,407 total
includes taxes & fees
Nov 2 - Nov 3
Nate`s Cabin at Water`s Edge
A hotel room with a bed, bedside tables, a desk, a chair, and a wooden dresser.

4. North Lima OH|King Bed|Smoking

North Lima OH|King Bed|Smoking
North Lima OH
10.0 out of 10, Exceptional, (103 reviews)
"Really peaceful stay, great spot for families!"
United States
Anonymous traveler
The price is ￥13,211
￥16,237 total
includes taxes & fees
Oct 21 - Oct 22
North Lima OH|King Bed|Smoking
A living room with two grey sofas, a teal console table, a kitchen in the background, and a mounted TV.

5. The Railroad Ranch Station 2

The Railroad Ranch Station 2
Youngstown
10.0 out of 10, Exceptional, (21 reviews)
"The Railroad Ranch was the perfect place to stay with my family and our puppy during our visit to the Canfield Fair! The house was spotless and in a wonderful location close to Mill Creek Park and Boardman shopping. Wayne, our host, went above and beyond to help us out with the EV charger and other amenities. We would absolutely recommend the Railroad Ranch to anyone staying in the Youngstown-Boardman area!"
United States
Niki
The price is ￥23,238
￥49,153 total
includes taxes & fees
Oct 21 - Oct 22
The Railroad Ranch Station 2
A bedroom with a large bed, a view of a forest through open doors, and a small balcony with chairs and a table.

6. Gwen`s Cottage at Water`s Edge

Gwen`s Cottage at Water`s Edge
Portersville
9.6 out of 10, Exceptional, (15 reviews)
"Perfect getaway! The property was beautiful and the host was fantastic!"
United States
Gwen H.
The price is ￥31,802
￥58,831 total
includes taxes & fees
Nov 5 - Nov 6
Gwen`s Cottage at Water`s Edge
A room with a round mirror, a desk with a small plant, a floor lamp, and a potted plant.

7. Apt 2 The Mod Squad

Apt 2 The Mod Squad
Masury
9.4 out of 10, Exceptional, (3 reviews)
"Clean, comfortable, lavish bathroom, "
United States
William
The price is ￥11,852
￥27,970 total
includes taxes & fees
Oct 21 - Oct 22
Apt 2 The Mod Squad
A stone sign for Geneva College with the text "Pro Christo Et Patria" and "Founded 1848".

8. Super Clean, Snug 2BR: By Geneva College, Fire Pit, Big TV & NFL Ticket!

Super Clean, Snug 2BR: By Geneva College, Fire Pit, Big TV & NFL Ticket!
Beaver Falls
10.0 out of 10, Exceptional, (12 reviews)
"We loved our stay at the Campus Cove on College Hill.We especially appreciated how nice and helpful the owners were. We will defiinitely come back. "
United States
Byron S.
The price is ￥16,308
￥40,202 total
includes taxes & fees
Oct 21 - Oct 22
Super Clean, Snug 2BR: By Geneva College, Fire Pit, Big TV & NFL Ticket!
A two-story house with a white exterior, a front porch, and a white picket fence.

9. Apartment on the Park

Apartment on the Park
Zelienople
9.8 out of 10, Exceptional, (143 reviews)
"Great little place to stay right in the heart of Zelie"
United States
KNOWLAN R.
The price is ￥11,852
￥16,664 total
includes taxes & fees
Oct 21 - Oct 22
Apartment on the Park
A living room with a checkered armchair, a grey sofa, a wooden bookshelf, and a decorative wreath on the wall.

10. Spacious 3 bedroom home with plenty of green space

Spacious 3 bedroom home with plenty of green space
Slippery Rock
10.0 out of 10, Exceptional, (31 reviews)
"House was very nice and in a perfect location"
United States
Ken C.
The price is ￥22,044
￥57,270 total
includes taxes & fees
Oct 21 - Oct 22
Spacious 3 bedroom home with plenty of green space
A kitchen with dark cabinets, a granite countertop, and a dining area with a table and chairs.

11. Breckenridge Suites #2 - One-Bedroom Suite Perfect for Business or Leisure

Breckenridge Suites #2 - One-Bedroom Suite Perfect for Business or Leisure
Grove City
9.4 out of 10, Exceptional, (9 reviews)
"Awesome stay!"
United States
Yuliya
The price is ￥12,484
￥24,048 total
includes taxes & fees
Oct 27 - Oct 28
Breckenridge Suites #2 - One-Bedroom Suite Perfect for Business or Leisure
A wooden desk with a black office chair, a small window, and a framed picture on the wall.

12. Pet-Friendly 2-Story Home Near Youngstown - Fast WiFi - Quiet Area

Pet-Friendly 2-Story Home Near Youngstown - Fast WiFi - Quiet Area
Struthers
9.8 out of 10, Exceptional, (10 reviews)
"Amazing stay!"
United States
Carter V.
The price is ￥22,984
￥30,329 total
includes taxes & fees
Oct 27 - Oct 28
Pet-Friendly 2-Story Home Near Youngstown - Fast WiFi - Quiet Area
A living room with a fireplace, sofa, armchair, coffee table, and a TV mounted on the wall.

13. Spacious 3 level 4-bedroom house- 2 Full kitchens-2 king beds and 3 queen beds.

Spacious 3 level 4-bedroom house- 2 Full kitchens-2 king beds and 3 queen beds.
Campbell
10.0 out of 10, Exceptional, (2 reviews)
"We had a family wedding and it was perfect stay for my brothers family and mine!"
United States
Laura D.
The price is ￥32,669
￥80,098 total
includes taxes & fees
Oct 21 - Oct 22
Spacious 3 level 4-bedroom house- 2 Full kitchens-2 king beds and 3 queen beds.
A round glass table with a decorative centerpiece, surrounded by wooden furniture and potted plants.

14. Simple Stay for Family and Friends, 2-bedroom upstairs apartment in Boardman.

Simple Stay for Family and Friends, 2-bedroom upstairs apartment in Boardman.
Youngstown
10.0 out of 10, Exceptional, (15 reviews)
"Clean and comfortable stay. Everything was in working order and close to where we needed to be. Would recommend!"
United States
Vanessa B.
The price is ￥12,484
￥23,545 total
includes taxes & fees
Oct 25 - Oct 26
Simple Stay for Family and Friends, 2-bedroom upstairs apartment in Boardman.
A white house with a green door, a yellow door, and a porch with a chair.

15. Apt A The Yellow Shuttered House

Apt A The Yellow Shuttered House
Sharon
9.2 out of 10, Wonderful, (5 reviews)
"Great value and very convenient for my visit to the area."
United States
MARK
The price is ￥12,484
￥29,275 total
includes taxes & fees
Oct 28 - Oct 29
Apt A The Yellow Shuttered House
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

16. Cozy fully remodeled home in Hermitage.

Cozy fully remodeled home in Hermitage.
Hermitage
10.0 out of 10, Exceptional, (3 reviews)
"Miss Pats place is hands down one of the nicest places we have stayed at. It was so incredibly clean and organized! Such a perfect house for a small gathering! Thank you Bob and Monica for being wonderful hosts!"
United States
Virginia
The price is ￥15,310
￥42,364 total
includes taxes & fees
Oct 25 - Oct 26
Cozy fully remodeled home in Hermitage.
A living room with a plaid sofa, a blue armchair, a glass coffee table, a lamp, and a framed picture on the wall.

17. The Yellow-Shuttered House apt B

The Yellow-Shuttered House apt B
Sharon
10.0 out of 10, Exceptional, (6 reviews)
"The property was well kept up and pet friendly! And I will definitely stay here again when I'm in the area.. The host went on and above to make sure I had everything for a great stay.. "
United States
Matthew B.
The price is ￥11,730
￥28,573 total
includes taxes & fees
Nov 3 - Nov 4
The Yellow-Shuttered House apt B
A modern kitchen with a wooden countertop, stainless steel appliances, and a ceiling fan.

18. Beautiful Home at 446 Frank & Fourth

Beautiful Home at 446 Frank & Fourth
Sharon
9.0 out of 10, Wonderful, (33 reviews)
"Very accommodating, clean home!"
United States
A R.
The price is ￥15,786
￥34,530 total
includes taxes & fees
Oct 22 - Oct 23
Beautiful Home at 446 Frank & Fourth
A living room with a flat-screen TV on a stand, a glass coffee table with coasters, a grey sofa, and a dining area in the background.

19. Apt 3 Comfortable and Convenient

Apt 3 Comfortable and Convenient
Masury
8.6 out of 10, Excellent, (4 reviews)
"It was a very comfortable stay. It was convenient for the purpose of my trip. I will truly make this my favorite spot when I travel to Pennsylvania. Thank you "
United States
Marjorie R.
The price is ￥11,852
￥28,128 total
includes taxes & fees
Nov 16 - Nov 17
Apt 3 Comfortable and Convenient
A wooden deck with a metal chair, a welcome mat, and potted plants.

20. "Simple Stay" Conveniently located to everything!

"Simple Stay" Conveniently located to everything!
Youngstown
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful communication, great host and location"
United States
Kelly H.
The price is ￥12,958
￥21,965 total
includes taxes & fees
Nov 2 - Nov 3
"Simple Stay" Conveniently located to everything!
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 Oakland Hotel Reviews

Wingate by Wyndham Grove City

Wingate by Wyndham Grove City

10/10 Excellent
"The breakfast was good and the lady though could be a little was very friendly and attentive. The rooms was clean and nice."
David 1-night trip
Posted 6 hours ago
Wingate by Wyndham Grove City

Find out more about Oakland

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

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

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

Frequently asked questions

Can I find a vacation rental in Oakland?

Yes, we have vacation rentals close to top points of interest in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Oakland?

Stien Oasis: Heated Indoor Pool Oasis With Theater, Bar&Tennis Court.: Visitors like this Oakland vacation home rental. It offers an indoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and an arcade game room so you can immerse yourself in your vacation.

What’s there to see and do in Oakland?

Explore the area and family-friendly sights such as Chuck E. Cheese's, or get out into nature at a spot like Moraine State Park. In the larger area, you’ll find Scottish Rite Cathedral and Westminster College.

What’s a vacation rental in Oakland like?

A vacation rental is a private property you can book for a couple of days or more in Oakland. Vacation rentals feature extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.