South Side All inclusive Holidays
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Top All-inclusive holiday packages in South Side
- Hyatt House Pittsburgh/Bloomfield/Shadyside
9 Oct - 13 OctHyatt House Pittsburgh/Bloomfield/Shadyside + Flight
Bloomfield4 nights3.0 star property9.0/10 - Wonderful (1,009 reviews)"Excellent stay! Thank you to all the staff!"Reviewed August 5, 2026Return • Edinburgh (EDI) - Pittsburgh (PIT)EDI - PIT • 1 stop PIT - EDI • 1 stop£1,372£1,128found 22 hours agoper traveller - Stay Pittsburgh
25 Sept - 29 SeptStay Pittsburgh + Flight
Downtown Pittsburgh4 nights2.0 star property8.0/10 - Very good (314 reviews)"Very responsive, great location, awesome hosts! 10/10 would recommend."Reviewed July 31, 2026Return • Edinburgh (EDI) - Pittsburgh (PIT)EDI - PIT • 1 stop PIT - EDI • 1 stop£1,934£1,456found 23 hours agoper traveller - The Westin Pittsburgh, a Marriott Hotel
9 Oct - 13 OctThe Westin Pittsburgh, a Marriott Hotel + Flight
Downtown Pittsburgh4 nights4.0 star property8.6/10 - Excellent (1,001 reviews)"The staff at the Westin was extremely helpful and proactive. The initial room they gave us had some issues, including a smoke-like smell (not cigarette smoke). As soon as we notified reception, someone handled it extremely professionally, and within minutes we were moved to a much better room."Reviewed August 3, 2026Return • Edinburgh (EDI) - Pittsburgh (PIT)EDI - PIT • 1 stop PIT - EDI • 1 stop£1,789£1,473found 22 hours agoper traveller - Joinery Hotel Pittsburgh, Curio Collection by Hilton
9 Oct - 13 OctJoinery Hotel Pittsburgh, Curio Collection by Hilton + Flight
Downtown Pittsburgh4 nights4.0 star property8.6/10 - Excellent (1,606 reviews)"I nice and clean."Reviewed August 6, 2026Return • Edinburgh (EDI) - Pittsburgh (PIT)EDI - PIT • 1 stop PIT - EDI • 1 stop£1,453£1,204found 22 hours agoper traveller - Etage Executive Living
9 Oct - 13 OctEtage Executive Living + Flight
Downtown Pittsburgh4 nights3.5 star property9.2/10 - Wonderful (1,862 reviews)"Stayed in a one bedroom King and the room (1105) was great except two things. The King bed was a true King size but the mattress was more of a futon mattress than a real mattress. It was only about 4 inches thick so it didn't really provide much support. Other thing is the pull out couch. The staff do not clean under or between the cushions. If you need to use the pull out make sure you call ahead and tell them to clean it. I always bring an inflatable for the kids so i kept that couch..."Reviewed August 6, 2026Return • Edinburgh (EDI) - Pittsburgh (PIT)EDI - PIT • 1 stop PIT - EDI • 1 stop£1,424£1,207found 22 hours agoper traveller
What to do in South Side
Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers
Top All-inclusive South Side Hotels
SpringHill Suites by Marriott Pittsburgh Southside Works
SpringHill Suites by Marriott Pittsburgh Southside Works"Great property in a great location!"
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG"first of all i put down the wong date and bought 2 rooms instead of one room and only stayed in one room. so i got charged an extra night and had to extent my stay with holiday inn . it was an night mare and the htel said i had to ask for a refund thru expedia witch is abig pain in my butt . there was no towels at the pool for two days in a row and having two kids that are wet and had to run upstair just to get towels. overall i am very disappointed"
HYATT house Pittsburgh-South Side
HYATT house Pittsburgh-South Side"This property is brand new. Breakfast is really good. The room has a small kitchen."
2 Mi to Market Sq! Row House w/ Dedicated Office
2 Mi to Market Sq! Row House w/ Dedicated Office"Great house! Feels brand new."
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere"Very accessible by car and easy to get to other parts of city"
Iron City of South Side Flats Charming 2-bedroom Unit
Iron City of South Side Flats Charming 2-bedroom Unit"Minus parking great stay will be back "
Steel City of South Side Flats Charming 2-Bedroom Unit
Steel City of South Side Flats Charming 2-Bedroom Unit"Great location, appreciated off-street gated parking at residence. Unit is updated and clean with lots of modern amenities. Had a great visit, would definitely stay here again."
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 £1,128 – 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.