Title: South Shore Vacation Packages 2026 from $301 | Expedia.com [South Shore Travel Guide](https://expedia.com/Pittsburgh-South-Shore.dx553248634333002587)[Hotels in South Shore](https://expedia.com/South-Shore-Pittsburgh-Hotels.0-n553248634333002587-0.Travel-Guide-Filter-Hotels)[Flights to Pittsburgh](https://expedia.com/Cheap-Flights-To-Pittsburgh.d601717.Travel-Guide-Flights)[Things to do in Pittsburgh](https://expedia.com/Things-To-Do-In-Pittsburgh.d601717.Travel-Guide-Activities)[Car Rentals in South Shore](https://expedia.com/Car-Rentals-In-South-Shore.d553248634333002587.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248634333002587/2b17da6a-c3b2-4aff-ac99-a74d1fd9f910.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Shore Vacations from $301 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your South Shore Vacation Avoid the hassle of travel planning with a South Shore vacation package. With all the details organized before you go away, all that's left for you to do is enjoy this riverside neighborhood's cycling, views and walking. Start your trip to South Shore by heading to nearby attractions such as [Acrisure Stadium](https://www.expedia.com/Acrisure-Stadium-North-Shore.d6058087.Vacation-Attraction), [University of Pittsburgh](https://www.expedia.com/University-Of-Pittsburgh-Oakland.d6090505.Vacation-Attraction) and [PNC Park](https://www.expedia.com/PNC-Park-North-Shore.d6034814.Vacation-Attraction). Stop daydreaming and start doing. When it's time to book your next vacation to South Shore, Expedia is here to help. ## The Latest South Shore Vacation Packages Price found within the past 48 hours. Click for updated prices. ![Americas Best Value Inn Pittsburgh Airport](https://images.trvl-media.com/lodging/1000000/30000/24900/24864/bce8953f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Americas Best Value Inn Pittsburgh Airport $301 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 6.6/10 (1,006 reviews) Room was clean. Took a while to heat up. Reviewed on Feb 4, 2026 ![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/b0ce2278_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wyndham Grand Pittsburgh Downtown Downtown Pittsburgh $380 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 8.2/10 Very Good! (3,437 reviews) I had a great stay at the Wyndham in downtown Pittsburgh. The location is excellent—right in the heart of the city and within easy walking distance of restaurants, shops, and the riverfront. It made exploring the area incredibly convenient. The hotel staff was friendly and welcoming from the moment I checked in. Everyone I interacted with was helpful and professional, which really made the stay feel comfortable and stress-free. My room was clean, spacious, and well maintained. The bed was very comfortable, and the views of the city were a nice bonus. I also appreciated how quiet the room was at night, which made it easy to relax and get a good night’s sleep. Overall, this is a great choice if you’re visiting downtown Pittsburgh. Between the convenient location, comfortable rooms, and excellent service, I would definitely stay here again. Reviewed on Mar 16, 2026 ![Holiday Inn Express & Suites Pittsburgh North Shore by IHG](https://images.trvl-media.com/lodging/11000000/10920000/10914800/10914769/91dbd17d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express & Suites Pittsburgh North Shore by IHG North Shore Save 100% on your flight $674 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 8.6/10 Excellent! (1,399 reviews) Clean room. Convenient location. Heard some road noise through the night but if you’re a heavy sleeper it shouldn’t bother you. One of the elevators was out of order so it took a little longer to get to and from 8th floor. I would most likely stay again for location. Reviewed on Mar 9, 2026 ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton Downtown Pittsburgh Save 100% on your flight $831 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 8.4/10 Very Good! (1,475 reviews) The staff were all very friendly and welcoming. The rooms and all of the public areas were very clean and well maintained. I will say the room layout was a bit awkward. Having the hangers for clothes right above the refrigerator allowed for the clothes to constantly get in the way of closing the refrigerator, and overall it didn’t seem like the space was used efficiently. The hotel was a great location and easily accessible. I would probably not use the valet parking next time, as there is a public lot adjacent to the hotel, and a public garage approximately 100 steps away, both of which are available for half of what the valet charge is. Reviewed on Mar 16, 2026 ![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/0729901f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Downtown Pittsburgh at The Pennsylvanian Downtown Pittsburgh $551 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Boston (BOS) to Pittsburgh (PIT) 8.2/10 Very Good! (71 reviews) Best place I have stayed in Pittsburgh Reviewed on Mar 16, 2026 ## Where to stay in South Shore Find the best South Shore areas and neighborhoods for the activities you enjoy most. [Learn more about South Shore](https://expedia.com/Pittsburgh-South-Shore.dx553248634333002587) ![Downtown Pittsburgh which includes a bridge and a river or creek](https://images.trvl-media.com/place/6057662/7df71e93-fe04-46c9-a8b8-caf07e34fbb5.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Pittsburgh 2 out of top 10 points of interest in this area 4.5/5(2,251 area reviews) Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks. [Find hotel + flight trips in Downtown Pittsburgh](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Pittsburgh&DestID=6057662&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![North Shore showing a river or creek, a bridge and a city](https://images.trvl-media.com/place/553248633938969308/c1d2f3a4-eff8-47ed-b1af-f88f96028a9d.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### North Shore 2 out of top 10 points of interest in this area 4.5/5(567 area reviews) Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations. [Find hotel + flight trips in North Shore](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20Shore&DestID=553248633938969308&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![View of the Strip District, from Frank Curto Park in Pittsburgh, Pennsylvania](https://images.trvl-media.com/place/6343592/dc99580f-c44b-45af-9529-30dbfbc703a3.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Strip District 4/5(17 area reviews) Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months. [Find hotel + flight trips in Strip District](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Strip%20District&DestID=6343592&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![South Shore showing a city, landscape views and a river or creek](https://images.trvl-media.com/place/553248634333002587/46d6c5fe-6780-4437-8b35-94be38c886fb.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Mount Washington Restaurant Row and scenic leafy parks lie along the ridge of a famous hill, where George Washington mapped the terrain for the British. [Find hotel + flight trips in Mount Washington](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Mount%20Washington&DestID=6343586&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![PITTSBURGH, PENNSYLVANIA, USA 4-30-2018 Mellon Park. Designed in 1929 and later donated to the city by Richard Mellon as part of his estate in the Shadyside neighborhood of the the City](https://images.trvl-media.com/place/6156339/b2f1141a-234f-4e0d-9662-7e5f7d7d28a0.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Shadyside 4.5/5(37 area reviews) Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible. [Find hotel + flight trips in Shadyside](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Shadyside&DestID=6156339&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## South Shore Hotel Deals ![Sheraton Pittsburgh Hotel at Station Square](https://images.trvl-media.com/lodging/1000000/30000/20400/20319/b7421ee2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Pittsburgh Hotel at Station Square 300 West Station Square Drive Pittsburgh PA Fully refundableReserve now, pay when you stay $152 nightly $173 total Apr 5 - Apr 6 Total with taxes and fees 9/10 Wonderful! (1,049 reviews) Keep in mind $25/night parking! Reviewed on Mar 12, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=20319&PinnedHotelID=20319&HadPinnedHotel=true®ionId=553248634333002587) ![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/b0ce2278_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Grand Pittsburgh Downtown 600 Commonwealth Pl Pittsburgh PA Fully refundableReserve now, pay when you stay $124 nightly $141 total Apr 5 - Apr 6 Total with taxes and fees 8.2/10 Very Good! (3,438 reviews) Rooms were SMALL. Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=25509&PinnedHotelID=25509&HadPinnedHotel=true®ionId=553248634333002587) ![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Joinery Hotel Pittsburgh, Curio Collection by Hilton 453 Boulevard of the Allies Pittsburgh PA Fully refundableReserve now, pay when you stay $126 nightly $143 total Mar 29 - Mar 30 Total with taxes and fees 8.4/10 Very Good! (1,480 reviews) The staff were all very friendly and welcoming. The rooms and all of the public areas were very clean and well maintained. I will say the room layout was a bit awkward. Having the hangers for clothes right above the refrigerator allowed for the clothes to constantly get in the way of closing the ... Reviewed on Mar 16, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=17900777&PinnedHotelID=17900777&HadPinnedHotel=true®ionId=553248634333002587) [See all 1,948 properties in South Shore](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F19%2F2026&endDate=3%2F20%2F2026®ionId=553248634333002587) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ### Discover the most popular places to visit in South Shore ![Smithfield Street Bridge](https://images.trvl-media.com/place/6078709/e5c6af7f-98ad-4ec6-8e14-6c491a9fbac8.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Station Square You can do some window-shopping at Station Square during your trip to Pittsburgh. Experience the acclaimed theater scene and entertainment choices in this vibrant area. [](https://expedia.com/Station-Square-South-Shore.d6078709.Vacation-Attraction) ![Monongahela Incline showing a gondola](https://images.trvl-media.com/place/6078693/75bc7d24-c8ee-47a0-9e5b-56dc55038fa9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Monongahela Incline Spectacular views of the Pittsburgh cityscape await at the top of the steepest funicular railway in the United States. [](https://expedia.com/Monongahela-Incline-South-Shore.d6078693.Vacation-Attraction) ### Things to do ![Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena](https://mediaim.expedia.com/localexpert/47588438/9191c759-53fb-49fa-8583-0093ee671ca3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena $93 per adult [](https://expedia.com/things-to-do/pittsburgh-penguins-ice-hockey-game-at-ppg-paints-arena.a47588438.activity-details) ![Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl](https://mediaim.expedia.com/localexpert/697587/fb378b65-03b5-422b-84c6-ec829fe06b75.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl $13 per adult [](https://expedia.com/things-to-do/pittsburgh-bar-hunt-party-through-pittsburgh-bar-crawl.a697587.activity-details) ![Pittsburgh: Beauty of the Burgh Bike Tour](https://mediaim.expedia.com/localexpert/4572811/f96e6be9-59d9-405e-9cf4-20718d608bf0.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pittsburgh: Beauty of the Burgh Bike Tour $59 per adult **94%** of travellers recommend [](https://expedia.com/things-to-do/pittsburgh-beauty-of-the-burgh-bike-tour.a4572811.activity-details) [See all activities in Pittsburgh](https://expedia.com/things-to-do/search?rid=553248634333002587) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.