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Vacation rentals in Oakmont

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Top-rated vacation rentals in Oakmont

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

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Home in Monroeville

4.81 out of 5 average rating, 185 reviews

Pittsburgh Hideaway - Pets - Private

-Discounts on weekly and monthly stays - Put in dates for prices. -1 bedroom house with 1 bath and everything you need for a comfortable stay. -House is tucked away, but also close to the highway and turnpike. -Walking distance to UPMC East, 6 minutes to Forbes Hospital, and min from major shopping/restaurants. -Pet friendly with a large yard (no fence). -Dog park only 7 minutes away - Monroeville Dog Park. Boyce Park and Penn Hills (fenced dog parks) 15 min away -TV- Amazon Stick to login

Mar 11 – 18

Home in Verona

4.87 out of 5 average rating, 247 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.

Feb 2 – 9

Guest suite in Pittsburgh

4.97 out of 5 average rating, 137 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.

Sep 5 – 10

Apartment in Pittsburgh

4.95 out of 5 average rating, 387 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!

Mar 12 – 19

Guest suite in Gibsonia

4.94 out of 5 average rating, 140 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.

Sep 15 – 22

Apartment in Pittsburgh

4.91 out of 5 average rating, 327 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.

Oct 31 – Nov 7

Guesthouse in Oakmont

4.97 out of 5 average rating, 75 reviews

Cozy Carriage House in Oakmont, PA

Newly renovated detached Carriage House with off-street parking. Sleeps 4 people comfortably with master bedroom on the main floor. Ideal for golfers at the famous Oakmont Country Club or a few days stay in beautiful Oakmont, PA. Living room and Main Bedroom equipped with Smart TVs. Standard cable + HBO. Private patio area with seating. 20 minutes from Downtown Pittsburgh & 5 minutes from PA Turnpike. May not be suitable for small children. Must be able to climb steps.

Jan 19 – 26

Cabin in Pittsburgh

4.92 out of 5 average rating, 126 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.

Oct 11 – 18

Apartment in Pittsburgh

4.99 out of 5 average rating, 144 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!

Aug 22 – 29

Apartment in Glenshaw

4.95 out of 5 average rating, 195 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

Jul 25 – Aug 1

Home in Irwin

5.0 out of 5 average rating, 108 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 .

Dec 4 – 11

Guest suite in Pittsburgh

4.94 out of 5 average rating, 198 reviews

Sweet Mid-Century Modern Suite/Attached Garage

Half-above ground basement studio with secured garage parking (keyless entry) in quiet, peaceful, "Mr. Rogers" neighborhood. Mid-century comfort with modern amenities and eclectic furnishings. Private bath and kitchenette. New queen-size bed, new shower, and new three-quarter sofa bed. Comfortable for single, couple, and 1-2 children. Ground level patio. No stairs or steps.

Jul 13 – 20

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

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Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Oakmont vacation 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 vacation rentals in Oakmont

Bungalow in Oakmont

4.98 out of 5 average rating, 63 reviews

Oakmont Home with Hot Tub

Apartment in Springdale

4.78 out of 5 average rating, 41 reviews

2br gem in cute small town.

May 29 – Jun 5

Apartment in Verona

4.96 out of 5 average rating, 90 reviews

The Sycamore BnB @ 10.7 Marina

Aug 10 – 17

Home in Monroeville

5.0 out of 5 average rating, 12 reviews

Monroeville 2 bedroom 2 queen size beds

Dec 2 – 9

Home in New Kensington

4.98 out of 5 average rating, 64 reviews

Mid-Century Burrell Bungalow

Feb 23 – Mar 2

Apartment in Aspinwall

4.97 out of 5 average rating, 35 reviews

Aspinwall 1 bedroom Apartment

Jan 22 – 29

Home in Brackenridge

4.8 out of 5 average rating, 15 reviews

Cozy two bedroom

Sep 30 – Oct 7

Apartment in Pittsburgh

5.0 out of 5 average rating, 7 reviews

Upscale King Suite by WholeFoods

Jan 2 – 9

Quick stats about vacation rentals 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	$30 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Oakmont?
Yes! Work meets play with ease at over 10 vacation rentals in Oakmont featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Bed And Breakfast Rentals in Oakmont?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do bed and breakfast rentals in Oakmont have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Oakmont have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Oakmont?
Four-legged friends are welcome in Oakmont. Choose from more than 10 vacation rentals for guests traveling with pets.
Do bed and breakfast rentals in Oakmont have free parking?
Absolutely! We offer over 10 bed and breakfast rentals with free parking in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oakmont have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Oakmont?
Oakmont has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Oakmont?
Experience the best of Oakmont with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Oakmont?
Make yourself at home in Oakmont by choosing from our most frequently booked neighborhoods. We have over 260 vacation rentals in Dark Hollow Road, over 260 vacation rentals in Upper Oakmont, and over 220 vacation rentals in Lower Oakmont.

Destinations to explore