South Side Beach Holidays

Book a Beach Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Top flight + Beach hotel deals in South Side

Price found within the past 48 hours. Click for updated prices.
EVEN Hotel Pittsburgh Downtown by IHG

EVEN Hotel Pittsburgh Downtown by IHG

Downtown Pittsburgh
£1,076
per person
28 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.8/10 Excellent! (1,063 reviews)
I enjoyed my 3-night stay here. Bed comfortable, room clean and everything was in it's place. Breakfast was great every morning with a good selection of offerings. Staff was friendly and helpful.

Reviewed on 25 Sept 2026

The Inn on Negley

The Inn on Negley

Shadyside
£1,128
per person
28 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
10/10 Exceptional! (224 reviews)
So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.

Reviewed on 23 Sept 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

Downtown Pittsburgh
£1,174
per person
28 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.4/10 Very good! (1,106 reviews)
The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh
£1,169
per person
28 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!

Reviewed on 14 Sept 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh
£1,107
per person
28 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.6/10 Excellent! (1,639 reviews)
Don't see what you're looking for?
See all available trips from London to South Side
View all trips

4 Night Beach holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

Downtown Pittsburgh
£913
per person
29 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8/10 Very good! (325 reviews)
The property was located in a good area for what we where there for. The staff was friendly and made sure we were taken care of. Our check-in time was 3pm we arrived around 4pm. Upon entering the property it was clean and smelled amazing. Once we made it to our room it wasn't clean the bedding was still on from the previous guest, microwave was dirty as well as the floor had a sticky substance on it which means it hadn't been mopped, the TV in the bedroom did not work. We called the property immediately left a message and they called us right back. They apologized and had a young man who spoke no English (which made it hard to communicate) he apologized again and finished cleaning the apartment and changed the bedding. Once he finished the property called back and offered a discount which we still haven't received. I will suggest that the owners of this property do a deep clean. A fresh coat of paint or even wiping the walls down would work as well as changing the shower curtains. I don't think we will come back here.

Reviewed on 24 Sept 2026

The Inn on Negley

The Inn on Negley

Shadyside
£1,030
per person
29 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
10/10 Exceptional! (224 reviews)
So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.

Reviewed on 23 Sept 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

Downtown Pittsburgh
£1,042
per person
29 Oct - 2 Nov
found 1 hour ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.4/10 Very good! (1,106 reviews)
Don't see what you're looking for?
See all available trips from London to South Side
View all trips

Find your perfect South Side beach holiday

How can I book the best beach holidays in South Side?

Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your South Side beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options.

Can I book cheap beach holidays in South Side?

For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable South Side beach holidays, which start from £913. Prices and availability are subject to change. Additional terms may apply.

When can I go on a quiet beach holiday in South Side?

Enjoy out-of-season seclusion on a beach holiday to South Side during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too.

Why should I book family holidays in South Side with beach access?

If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties.

How can I find a South Side beachfront holiday?

For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water.

How can I book last-minute South Side beach holidays?

Add a little spontaneity to your beach holiday by looking for a last-minute deal in South Side. If you have set dates, pop them into the search and see what heaven awaits in just a few days.

Can I find South Side beach holidays which are all inclusive?

A beach holiday to South Side is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available.

Can I book a South Side beach trip with free cancellation and/or flexible dates?

Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details.

Why should I book a South Side beach holiday with Expedia?

Our huge range of accommodation and flights mean you’ll find the best beach holidays in South Side on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea.

Things to do

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

£15
per traveller
Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers
Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

£30
per adult
100% of travellers recommend
Pittsburgh Pirates Baseball Game at PNC Park
Picture 4 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

£22
per adult
86% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
See all activities in South Side

More holidays you might like

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holiday packages
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Where to go when
Where to go when

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.