Oakland Holiday Rentals

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Holiday Rentals in Oakland

Country Cottage get away w/ fire pit & breath-taking scenery

10.0 out of 10, Exceptional, (37)
"What a wonderful surprise experience. This is a hidden gem outside of the city and surrounding suburbs. The hosts communicated well. Everything was easy and our time was very intimate and lovely. We will be back. Thank you. "
The price is AU$313
includes taxes & fees
29 Nov - 30 Nov
Country Cottage get away w/ fire pit & breath-taking scenery

Lake Cottage with Year Round Swim Spa, Amenities, and Beautiful Views!

10.0 out of 10, Exceptional, (20)
"This house is deceivingly huge on the inside. Everything is clean and well stocked. Lots of seating and sleeping. The pool is amazing! Comfy bed. Very responsive owners. Could not have been better. We would definitely stay again for the pool alone. "
The price is AU$1,068
includes taxes & fees
30 Nov - 1 Dec
Lake Cottage with Year Round Swim Spa, Amenities, and Beautiful Views!

Modern Getaway in Amish Country

10.0 out of 10, Exceptional, (51)
"Great property in New Wilmington but not to far from New Castle shops and restaurants. The property has a great layout with comfortable furnishings, it was perfect for the 4 of us. Everything was in working order and none of the furnishings were overworn. We will recommend to friends and we will stay here again when visiting the area."
Modern Getaway in Amish Country

Beautiful Home at 446 Frank & Fourth

8.6 out of 10, Excellent, (11)
"I needed 1 night in this general location with more than 1 bedroom. I planned to spent little time in the property beyond sleeping. This property met my needs and was as advertised (acceptable housing with a low-end cost). Walking distance to restaurants and Wi-Fi provided. I was worried about potential theft/damage to my vehicle as it was parked openly overnight, but it was fine. Property was clean and neat. For the price, I accept a few minor imperfections. I was surprised that the host fee...
The price is AU$329
includes taxes & fees
1 Dec - 2 Dec
Beautiful Home at 446 Frank & Fourth

Halfway between New York and Chicago

10.0 out of 10, Exceptional, (51)
"The house was everything they advertised. Very clean and well kept. All amenities were as advertised. The extra snacks and drinks provided were a nice touch. Beds were comfortable. Only complaint-tv remote did not work due to dead batteries with no replacements. But we made due with no issues! Would stay here again in a heart beat!"
The price is AU$392
includes taxes & fees
1 Dec - 2 Dec
Halfway between New York and Chicago

Private Cottage minutes from Moraine State Park and McConnell's Mill State Park.

10.0 out of 10, Exceptional, (8)
"This is the perfect place to enjoy a few crisp fall days! "
Private Cottage minutes from Moraine State Park and McConnell's Mill State Park.

Cozy Youngstown Apartment w/ Central A/C + Heating

2.5 star property
10.0 out of 10, Exceptional, (1)
"It was close to everything i needed and yet peaceful"
Cozy Youngstown Apartment w/ Central A/C + Heating

The Railroad Ranch - Station 3 (3 bedrooms)

9.8 out of 10, Exceptional, (8)
"We had a very pleasant stay at the Railroad Ranch. We were in town for a baby shower and needed a central place to stay so we could visit relatives that live in the area. We could not have picked a better spot. It is close to shopping and restaurants. The house has everything you need for a comfortable stay. The area is quite, and I found it be very safe. "
The Railroad Ranch - Station 3 (3 bedrooms)

Down Town Fancy Fancy Upscale 2 Bedroom Loft

10.0 out of 10, Exceptional, (1)
"I was very impressed with this cute little downtown apartment right by the historic district (we walked to restaurants a number of times). It was extremely comfortable, beautifully decorated with all of the extras, like a 5 star hotel. We’ll be booking this one again! The owner was perfect in communication and very kind."
The price is AU$535
includes taxes & fees
28 Nov - 29 Nov
Down Town Fancy Fancy Upscale 2 Bedroom Loft

Peaceful log home retreat.

8.8 out of 10, Excellent, (5)
"Had a wonderful stay. Property was beautiful and the house was perfect."
Peaceful log home retreat.

Historic IronMaster House at Springfield Falls

10.0 out of 10, Exceptional, (7)
"Charming 1800's house, comfortable accommodations, large supportive beds, oversized bathrooms, well equipped kitchen and very large dining room. I stayed here with 5 other women and we had plenty of room to spread out after a long day of shopping. If you love vintage houses and creaky floors this place is for you! We will be back!"
Historic IronMaster House at Springfield Falls

Apartment on the Park

10.0 out of 10, Exceptional, (77)
"Convenient stay"
The price is AU$149
includes taxes & fees
9 Dec - 10 Dec
Apartment on the Park

Woodland Oasis Cabin Apartment

10.0 out of 10, Exceptional, (16)
"Perfect little spot for a weekend getaway, this place had everything an apartment should and was a great, cozy, and quiet space! Would definitely stay here again in a heartbeat!"
The price is AU$148
includes taxes & fees
2 Dec - 3 Dec
Woodland Oasis Cabin Apartment

Luxurious retreat for body&soul/king suite/hot tub

10.0 out of 10, Exceptional, (18)
"Wonderful place to stay for everyone!!! Fishing, kayaking, camp fire, and the girls loved the shopping everyone had a great time!! House was set up great and super clean!! Our host was super also!! Thank you so much!’"
The price is AU$1,073
includes taxes & fees
28 Nov - 29 Nov
Luxurious retreat for body&soul/king suite/hot tub

Cozy Volant Ranch With Lakeview

9.6 out of 10, Exceptional, (11)
"Very welcoming, it had everything we needed."
The price is AU$389
includes taxes & fees
4 Dec - 5 Dec
Cozy Volant Ranch With Lakeview

Pet Friendly 3 bedroom 1 king,1 Queen,1 Full Bed Home

10.0 out of 10, Exceptional, (5)
"This property is just as advertised. The owners thought of everything. I was in town for the week and it was clean, safe and everything worked without a hitch. The fenced-in backyard was perfect for my dog. The property manager was available, knowledgable and non-intrusive. Could not recommened this place more!! "
Pet Friendly 3 bedroom 1 king,1 Queen,1 Full Bed Home

Pet-Friendly Beaver Falls Home, Work Remotely!

9.0 out of 10, Wonderful, (8)
"Perfect for large family gathering"
Pet-Friendly Beaver Falls Home, Work Remotely!

Cozy, Farmview Bungalow, with Central Location!

10.0 out of 10, Exceptional, (14)
"The bungalo was the perfect weekend getaway and the host was very attentive with any concerns I had. One of the best I've stayed in!"
Cozy, Farmview Bungalow, with Central Location!

Slippery Rock Cabin on the Creek. Close to McConnell’s Mill & Moraine St. Parks.

10.0 out of 10, Exceptional, (17)
"I've stayed here twice before with friends and family, due originally to proximity to an annual event in the area. This time, we came just for the Cabin, and got a chance to enjoy things our busy schedule hasn't let us do before; exploding the path along the creek, resting by the firepit, etc. The area is as gorgeous in the Autumn as we'd hoped, and the care that Anita puts into preparing the Cabin for guests is evident everywhere, and very much appreciated. Already looking forward to our...
Slippery Rock Cabin on the Creek. Close to McConnell’s Mill & Moraine St. Parks.

The Railroad Ranch Station 2

9.8 out of 10, Exceptional, (15)
"Great stay, very clean, easy check in and the host was Amazing! "
The Railroad Ranch Station 2
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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Other types of properties in Oakland you may be interested in

Wingate by Wyndham Grove City

2.5 star property
8.4 out of 10, Very good, (1103)
"It was a quick stop on a road trip Simple and Easy "
The price is AU$138
includes taxes & fees
10 Dec - 11 Dec
Wingate by Wyndham Grove City

Super 8 by Wyndham Grove City

2.0 star property
8.2 out of 10, Very good, (748)
"This place was quiet and clean. Someone is clearly working hard to update it. The mattress was AMAZINGLY COMFORTABLE. It had everything that my family needed for a one night stay. "
The price is AU$97
includes taxes & fees
1 Dec - 2 Dec
Super 8 by Wyndham Grove City

Holiday Inn Youngstown South, an IHG Hotel

3.0 star property
8.6 out of 10, Excellent, (547)
"Front desk had some difficulty finding our reservation but not their fault. Expedia had made an error and placed our reservation for the following night!! Luckily they had available rooms"
The price is AU$194
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Youngstown South, an IHG Hotel
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, 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 Oakland has to offer?

Lake Cottage with Year Round Swim Spa, Amenities, and Beautiful Views! : This holiday home rental outside of Oakland is located on a lake, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub.

What’s there to see and do in Oakland?

Explore the area and family-friendly sights such as Living Treasures Wild Animal Park, or get out into nature at a spot like Cascade Park. In the wider area, you’ll find Scottish Rite Cathedral and Westminster College.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for families.