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Holiday houses in Oakmont

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Top-rated holiday rentals in Oakmont

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Verona

4.87 out of 5 average rating, 250 reviews

Wyckoff-Mason Log House 1774 Historic Landmark

Stay in the historic Wyckoff-Mason House, a Pittsburgh Historical landmark. This beautifully kept log house built in 1774-75, still maintains the colonial charm of pre-revolutionary times. This property has a storied past, including local lore that it was the residence of William Penn’s brother and was visited by Benjamin Franklin. This relaxing getaway is located in one of Pittsburgh’s eastern suburbs. Get the best of the countries antiquity while visiting the city. We love all people.

21 – 28 Sept

$1,336 AUD total

Guest favourite

Guest suite in Pittsburgh

4.97 out of 5 average rating, 142 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

29 Aug – 3 Sept

Guest favourite

Home in Pittsburgh

4.92 out of 5 average rating, 264 reviews

Upscale Modern 2 BR Apartment

This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

20 – 27 June

$1,668 AUD total

Guest favourite

Apartment in Pittsburgh

4.95 out of 5 average rating, 392 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

21 – 28 Mar

Guest favourite

Guest suite in Gibsonia

4.94 out of 5 average rating, 141 reviews

Cozy Comfortable Retreat #1

Beautiful basement guest suite with a gas fireplace, full bath, kitchen with cooktop stove, mini refrigerator and microwave/convection oven. Enjoy off street parking in a quiet friendly neighborhood with outdoor patio. Close to shopping, restaurants, North Park and Hartwood Acres. Downtown Pittsburgh is less than 13 miles away which allows for easy access to all the sporting events Steeler games, Pirate games and Penguin games. Located less than 2 miles from the PA turnpike exit.

3 – 10 June

$1,222 AUD total

Guest favourite

Apartment in Pittsburgh

4.91 out of 5 average rating, 329 reviews

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

14 – 21 Jan

$1,143 AUD total

Guest favourite

Cabin in Pittsburgh

4.92 out of 5 average rating, 127 reviews

Cabin in Pittsburgh. 20 minutes to Pittsburgh

Please do not request booking until you have contacted the owner for pricing. The cabin is a perfect place to stay while visiting friends and family in Pittsburgh. Private and comfortable, clean and convenient to many locations in Pittsburgh. Only 20minutes to the city, and stadiums. The cost/night is $135.00 for 2 adults. Extra adults (18 and over) are $25.00/adult/day. Children under 18 are $10.00/child/day. Children under 2 are free. Dogs are $10.00/day.

28 Aug – 4 Sept

$1,902 AUD total

Guest favourite

Apartment in Pittsburgh

4.99 out of 5 average rating, 145 reviews

504 Bascom Ave Serene Luxury

Nestled in the middle of an adorable community of stone cottages, this historic structure built in 1938 was the first home John Mattys built in this neighborhood. He went on to build all the houses on Mattys (named after himself) and Oceanas Avenues (named for the sisters that commissioned and lived in this duplex). Re-imagined for contemporary lifestyles, 504 Bascom is your cozy cottage but with all the amenities you deserve. I look forward to hosting you!

28 Sept – 5 Oct

$1,489 AUD total

Guest favourite

Apartment in Glenshaw

4.95 out of 5 average rating, 200 reviews

The Camera Stop

Open and bright private apartment located in the Fox Chapel area. Entire apartment was recently remodeled with all new furnishings and fixtures. We are located only 20 minutes from Downtown Pittsburgh and 15 minutes to Heinz Field, PPG Paints Arena, and PNC Park. This area is close to shopping, restaurants, grocery stores and the PA Turnpike. Jennifer is my office manager and your contact for any bookings or questions you may have. NO SMOKING

27 Sept – 4 Oct

Guest favourite

Home in Irwin

5.0 out of 5 average rating, 110 reviews

Our cozy contemporary home near PA turnpike

Enjoy this peaceful, private residence conveniently located <5 miles from PA turnpike exit 67 with quick access to many restaurants and retail establishments. This is a nicely appointed and recently renovated ranch home in a residential neighborhood with a peaceful outdoor space. There is an open concept living room, dining area and new modern kitchen with stainless steel appliances. The bedrooms have comfortable beds with down comforters .

7 – 14 Jan

$1,374 AUD total

Guest favourite

Home in Export

4.97 out of 5 average rating, 117 reviews

Peaceful Export home with Large Deck

Enjoy this newly remodeled home with a spacious master bedroom and large deck. You'll be pleasantly surprised by the secluded and private feel of this space. It is perfect for a get away with family, friends, or all by yourself! Come relax, have fun, and explore all that the small town of Export has to offer. 25 minutes from Pittsburgh city center, 15 minutes from Monroeville, right off the Westmoreland Heritage Trail.

12 – 19 Dec

$2,116 AUD total

Guest favourite

Townhouse in Pittsburgh

4.91 out of 5 average rating, 122 reviews

Family friendly *garage parking *10 min DT Pitt

Nestled in a quiet neighborhood, our home is the perfect haven for families looking to explore the vibrant city of Pittsburgh. With ample space for everyone to spread out and relax, our home offers a comfortable and inviting atmosphere. We offer premium amenities, including whole bean coffee, tea selection, soft towels, toiletries, and in-unit laundry (w/d) with laundry supplies provided.

16 – 23 June

$2,090 AUD total

Holiday rentals for every style

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Popular amenities for Oakmont holiday rentals

Free parking on premises

Air conditioning

Stay near Oakmont's top sights

Oakmont Bakery25 locals recommend

The Lot at Edgewater6 locals recommend

Carnivores11 locals recommend

The Pub at 3335 locals recommend

Hoffstot's Cafe Monaco6 locals recommend

The Oaks Theater4 locals recommend

Other great holiday rentals in Oakmont

Guest favourite

Guest suite in Pittsburgh

4.94 out of 5 average rating, 236 reviews

Warm & Cozy, Newly Remodeled Private Space.

22 – 29 Apr

$1,199 AUD total

Guest favourite

Apartment in Valencia

5.0 out of 5 average rating, 115 reviews

Inspired farmhouse apartment

12 – 19 Apr

$1,500 AUD total

Guest favourite

Townhouse in Pittsburgh

4.88 out of 5 average rating, 99 reviews

Modern/Industrial Townhouse in Lawrenceville

16 – 23 Sept

$1,232 AUD total

Home in Monroeville

4.81 out of 5 average rating, 187 reviews

Pittsburgh Hideaway - Pets - Private

15 – 22 Aug

$1,807 AUD total

Guest favourite

Guest suite in West Mifflin

4.99 out of 5 average rating, 106 reviews

Hilltop Suite, Quiet Street

4 – 11 Nov

$1,456 AUD total

Guest favourite

Apartment in East McKeesport

4.94 out of 5 average rating, 261 reviews

Quiet Luxury Apartment!

11 – 18 Jan

$1,618 AUD total

Guest favourite

Home in Pittsburgh

4.91 out of 5 average rating, 348 reviews

Urban converted gas station in heart of South Side

28 Nov – 5 Dec

$1,496 AUD total

Guest favourite

Apartment in Pittsburgh

4.94 out of 5 average rating, 191 reviews

MINIMALIST + MODERN 2BR in trendy PGH enclave

31 July – 7 Aug

$1,425 AUD total

Quick stats about accommodation in Oakmont

Total rentals
30 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
450 reviews
Nightly prices starting at
$45 AUD before taxes and fees

Destinations to explore