Photo by Linda Monteleone

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Featured Cottages in Oakdale

Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet

9.4 out of 10, Exceptional, (136)
"Very cute house on a dead end street, tucked away on the ridge in the woods, just a few minutes from downtown Carnegie. The house is very quirky but a lovely stay that feels private and easy to access all the things you’ll want from your stay in Pittsburgh!"
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet

Take it easy at this unique and tranquil getaway.

6.0 out of 10, (2)
"The home was exactly as I was expecting.. it’s an older home with older home issues. The bathroom floor was uneven in paces. The beds were comfortable and the kitchen adequate. There was a smoke detector that was NOT installed, it was lying in a drawer. My BIGGEST complaint was the fact that the dryer was broken. In correspondence with Chris he stated that he had told me that it would not be fixed until after our stay and when I corrected him that he did not tell me that his message became a bit...
Take it easy at this unique and tranquil getaway.

Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!

3.0 star property
Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!

Well-appointed Pittsburgh Home: 1 Mi to Dtwn!

3.0 star property
Well-appointed Pittsburgh Home: 1 Mi to Dtwn!

Pittsburgh Home Near Frick Park, 7 Mi to Dtwn

3.0 star property
Pittsburgh Home Near Frick Park, 7 Mi to Dtwn

Pittsburgh Home w/ Pool, Fire Pit + Game Room

3.0 star property
Pittsburgh Home w/ Pool, Fire Pit + Game Room

Pet-friendly Home - 100 Feet to Walnut Street

3.0 star property
9.0 out of 10, Wonderful, (2)
"I wasn’t thrilled the rental was on a second floor when I had my dogs. Pets, unfortunately, tend to move freely and I thought the guests on the first floor below us may have been annoyed with that. I also didn’t like having to haul our luggage up many stairs, including heavy video equipment I brought with me for this scheduled trip to attend an event. I also received many emails and text messages reminding me about the trip; and overlooked that the instructions said our entrance was in the...
Pet-friendly Home - 100 Feet to Walnut Street

Shadyside House - 100 Feet to Walnut Street!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The property was extremely well located, comfortable, and well appointed. I cooked meals, but there are many restaurants in the neighborhood too. I would stay here again without hesitation. "
Shadyside House - 100 Feet to Walnut Street!

This private residence is perfect for an extended stay or executive relocation..

This private residence is perfect for an extended stay or executive relocation..

Spacious Pittsburgh Rental: Walk to Frick Park!

3.0 star property
Spacious Pittsburgh Rental: Walk to Frick Park!

Cute Home w/ Patio ~ 7 Mi to Dtwn Pittsburgh

3.0 star property
4.0 out of 10, (1)
"Motion detector lights were very bright and non sense Hard mattress House older and dated"
Cute Home w/ Patio ~ 7 Mi to Dtwn Pittsburgh

Family-friendly Shadyside Gem Near Dtwn Pittsburgh

3.0 star property
Family-friendly Shadyside Gem Near Dtwn Pittsburgh

Charming West Mifflin House - 3 Mi to Kennywood!

3.0 star property
Charming West Mifflin House - 3 Mi to Kennywood!

Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice, well kept and easy to communicate with host/ owners. Would recommend! "
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

Modern Pittsburgh Home w/ Rooftop Deck & Backyard

3.0 star property
Modern Pittsburgh Home w/ Rooftop Deck & Backyard

Penn Hills Home ~ 11 Mi to Pittsburgh

3.0 star property
Penn Hills Home ~ 11 Mi to Pittsburgh

Pittsburgh Vacation Rental: 3 Mi to Downtown!

3.0 star property
Pittsburgh Vacation Rental: 3 Mi to Downtown!

Pittsburgh Retreat w/ Deck ~ 4 Mi to Dtwn!

3.0 star property
Pittsburgh Retreat w/ Deck ~ 4 Mi to Dtwn!

Pittsburgh Vacation Rental in Lawrenceville!

3.0 star property
Pittsburgh Vacation Rental in Lawrenceville!

Pittsburgh Row Home: Steps to Stadiums & Dtwn!

3.0 star property
Pittsburgh Row Home: Steps to Stadiums & Dtwn!
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 property types in Oakdale

Stay Pittsburgh

2.0 star property
7.6 out of 10, Good, (83)
"It was def worth the price you pay to stay "
The price is NZ$179
includes taxes & fees
11 Dec - 12 Dec
Stay Pittsburgh

Kasa South Side Pittsburgh

4.0 star property
8.6 out of 10, Excellent, (67)
"It's conveniently located with easy access to CMU, downtown etc. We love staying in this property. This is our 4th stay. we stay here when we come to drop off our kid to college or visit her. Apartment is very neat, self sufficient even for longer stays. Love it"
Kasa South Side Pittsburgh

The Warhola Bloomfield

4.5 star property
5.0 out of 10, (20)
"This place is incredible!! Walking distance to awesome neighborhoods, immaculately clean, comfy furniture and all amenities top-notch! I already want to plan more stays at this spot!!"
The price is NZ$217
includes taxes & fees
2 Dec - 3 Dec
The Warhola Bloomfield
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

Black Friday: Members save 30%+

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

Frequently asked questions

How much do cottages in Oakdale cost?
Rates for cottages in Oakdale range between and per night. No matter your budget, you’ll find the ideal place to relax and reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What is there to do in Oakdale near my cottage?
After you’ve unpacked your bags and settled in, set out and explore the amazing things Oakdale has for you to experience. Pittsburgh Botanic Garden is a popular attraction to add to your must-do list.