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South Side All inclusive Holidays

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  • Discover the most popular places to visit in South Side

    Rex Theater

    Rating: 6.0/10 (1 review)

    You can make plans for a show at Rex Theater during your trip to Pittsburgh. Visit the shops and top-notch restaurants in this family-friendly area.

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    What to do in South Side

    Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

    Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

    £15

    per traveller

    0% of travellers recommend

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    Top All-inclusive South Side Hotels

    Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

    A breakfast bar with various food items and a sign that says "Egg-Xactly The Start You Need".
    • Address: 20 S 10th St, Pittsburgh, PA, 15203, US
    • Location: South Side Flats, 0.7 mi from South Side
    • Star rating: 2.5/5
    • Guest rating: 8.2/10 (Very good, 1042 reviews)
    • Price: £79, includes taxes & fees, 14 Dec - 15 Dec, for Top All-inclusive South Side Hotels
    • Review: Plenty of parking, clean room, and good breakfast.

    HYATT house Pittsburgh-South Side

    An outdoor seating area with wicker furniture and a view of a river and buildings in the background.
    • Address: 2795 S Water St, Pittsburgh, PA, 15203, US
    • Location: South Side Flats, 0.8 mi from South Side
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 1000 reviews)
    • Price: £116, includes taxes & fees, 24 Nov - 25 Nov, for Top All-inclusive South Side Hotels

    SpringHill Suites by Marriott Pittsburgh Southside Works

    A modern dining area with a round table, chairs, and a sofa. There are large windows providing natural light and a view of the outdoors.
    • Address: 2950 S Water St, Pittsburgh, PA, 15203, US
    • Location: South Side Flats, 0.8 mi from South Side
    • Star rating: 3/5
    • Guest rating: 8.6/10 (Excellent, 1001 reviews)
    • Price: £98, includes taxes & fees, 7 Dec - 8 Dec, for Top All-inclusive South Side Hotels
    • Review: The hotel is situated next to train tracks that actually make the building shake slightly when they come by. Every train that came by I heard through the night and I was on the 6th floor. I will not return

    Traveler's Rest Hotel

    A spacious living room with a wooden ceiling, large windows with curtains, a leather sofa, a dining table, and a kitchen area.
    • Address: 27 S 6th St, Pittsburgh, PA, 15203, US
    • Location: South Side Flats, 0.9 mi from South Side
    • Star rating: 2/5
    • Guest rating: 9.6/10 (Exceptional, 133 reviews)
    • Price: £82, includes taxes & fees, 3 Dec - 4 Dec, for Top All-inclusive South Side Hotels
    • Review: Private but not attached bathroom/ shower wad different, but very clean and roomy.

    The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!

    A rustic bar area with wooden walls, two stools, a barrel, and a hanging light fixture.
    • Address: Pittsburgh, PA, US
    • Location: South Side Flats, 0.3 mi from South Side
    • Guest rating: 7/10 (Good, 2 reviews)
    • Review: "The location of the property is in the heart of the Southside and walkable to many places (Station Square, over the bridge to downtown, and lots of close places right on Carson St). Street parking is available, but there is not much of it. Our first night we had to pay to park in a public lot just around the corner. The next day I was able to get street parking, and then didn't move my car the rest of the weekend. This is an older apartment and located in a narrow alley. The property was...

    2615 Jane Down - Southside

    A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with wicker chairs and a round table.
    • Address: Pittsburgh, PA, US
    • Location: South Side Flats, 0.4 mi from South Side
    • Guest rating: 8.8/10 (Excellent, 5 reviews)
    • Price: £146, includes taxes & fees, 16 Nov - 17 Nov, for Top All-inclusive South Side Hotels
    • Review: Very clean modern place in nice neighborhood. Location great for walking. Found a vegan restaurant less than two blocks away.

    Birmingham Bridge Beauty Cozy Stay Near Downtown

    A living room with a blue sofa, a coffee table, and a painting of a sunset.
    • Address: Pittsburgh, PA, US
    • Location: South Side Flats, 0.3 mi from South Side
    • Guest rating: 2/10 (1 review)
    • Price: £126, includes taxes & fees, 15 Nov - 16 Nov, for Top All-inclusive South Side Hotels
    • Review: "While the host was responsive when requested, the check-in link provided with pictures was not live, making check-in confusing especially in the dark when we didn’t know the entrance was on the side of the building. The property is basic with no charm or comfort commodities which are usually found in a rental property such as this. There are two doors from the unit that gain access to other areas of the house that, while are locked to prevent people from gaining access to the apartment, they are...

    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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    All-inclusive South Side holidays: everything you need to know

    Can I book South Side all-inclusive holidays with airfare and meals?

    Use the all-inclusive filter to find amazing all-inclusive package holidays to South Side, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset.

    Why should I book a South Side adults-only all-inclusive holiday?

    If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to South Side and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday.

    Can I book last minute all-inclusive holidays to South Side?

    Last-minute breaks are a great way to find very cheap all-inclusive holidays to South Side. If you can be flexible with your holiday dates, browse our best South Side deals and use the all-inclusive filter to add everything that makes your hols perfect.

    Can I book a cheap all-inclusive South Side trip?

    There are some nifty little tricks to find pocket-friendly all-inclusive breaks in South Side. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply.

    What should I look for when booking a 5-star all-inclusive holiday to South Side?

    All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine.

    What should I consider when booking a South Side all-inclusive family holiday?

    If you’re holidaying with tots in tow, book an all-inclusive South Side package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind.

    How can I find the best deals on all-inclusive holidays to South Side in 2026/2027?

    There are great all-inclusive deals galore in South Side. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices.

    Can I book an all-inclusive South Side package with free cancellation and/or flexible dates?

    Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks.

    Why should I book an all-inclusive South Side package holiday with Expedia?

    With a huge range of all-inclusive South Side trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here.

    Explore a world of travel with Expedia