Beach Vacations in South Side 2026

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Flight and Beach hotel deals in South Side

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

The Oaklander Hotel, Autograph Collection

Oakland

CA $1,283

per person

Dec 17 - Dec 20

found 5 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Pittsburgh (PIT)

9.2/10 Wonderful! (826 reviews)

The Inn on Negley

Shadyside

CA $1,310

per person

Dec 17 - Dec 20

found 5 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Pittsburgh (PIT)

10/10 Exceptional! (221 reviews)

So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.

Reviewed on Sep 23, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,700

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.6/10 Excellent! (1,639 reviews)

Checking in took over 2 hours because rooms were ready.

Reviewed on Sep 24, 2026

Omni William Penn Hotel

Downtown Pittsburgh

CA $1,743

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

9.2/10 Wonderful! (2,047 reviews)

I was put in a room adjacent to the elevator bank, which there ARE APPROX 12 ELEVATORS, they travel continuous and sounded like a truck all night, great hotel , horrible room, got zero response when i complained to be moved

Reviewed on Sep 24, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

CA $1,875

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) 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 Sep 14, 2026

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3 Night Beach holidays in South Side

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

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,212

per person

Dec 17 - Dec 20

found 5 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Pittsburgh (PIT)

8.6/10 Excellent! (1,639 reviews)

Checking in took over 2 hours because rooms were ready.

Reviewed on Sep 24, 2026

The Inn on Negley

Shadyside

CA $1,310

per person

Dec 17 - Dec 20

found 5 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Pittsburgh (PIT)

10/10 Exceptional! (221 reviews)

So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.

Reviewed on Sep 23, 2026

The Oaklander Hotel, Autograph Collection

Oakland

CA $1,283

per person

Dec 17 - Dec 20

found 5 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Pittsburgh (PIT)

9.2/10 Wonderful! (826 reviews)

Don't see what you're looking for?

See all available trips from Columbus to South Side

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4 Night Beach holidays in South Side

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

Pittsburgh Marriott City Center

Downtown Pittsburgh

CA $1,530

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.2/10 Very good! (1,333 reviews)

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

CA $1,700

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

8.6/10 Excellent! (1,639 reviews)

Checking in took over 2 hours because rooms were ready.

Reviewed on Sep 24, 2026

Etage Executive Living

Downtown Pittsburgh

CA $2,019

per person

Dec 17 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Pittsburgh (PIT)

9.2/10 Wonderful! (1,895 reviews)

Super location! Great amenities, especially the athletic club. Friendly, helpful staff. Would definitely stay again.

Reviewed on Sep 24, 2026

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What are some benefits when booking beach vacations in South Side?

When you travel to the beach in South Side, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

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

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your South Side trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in South Side?

There are quite a few things you can do to get cheap beach vacations in South Side. Prices range from CA $1,212, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in South Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 10.

Why should I book family beach vacations?

When you're travelling with the family to South Side, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in South Side?

It's easy to find a beachfront vacation accommodation in South Side using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and South Side as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in South Side is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Pittsburgh. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in South Side

Pittsburgh’s Tropicana with outdoor year round hot tub. Fantastic location!

Pittsburgh PA

14 min walk from Rex Theater

Book a stay at this family-friendly vacation home in Pittsburgh. Enjoy free WiFi, laundry facilities, and patios. Popular attractions PPG Paints Arena and PNC ...

10/10 Exceptional! (62 reviews)

"Great place!"

Reviewed on Sep 8, 2026

King Bed | Free Parking | BBQ | Fire pit | Arcade

Pittsburgh PA

1 min walk from Rex Theater

Stay at this vacation home in Pittsburgh. Enjoy a garden, laundry facilities, and patios. Popular attractions PPG Paints Arena and PNC Park are located ...

9.8/10 Exceptional! (70 reviews)

"This property was amazing! The Southside Flats area is a great location! Brandon the host was very responsive to questions and concerns prior to and during our stay. The backyard patio was a nice feature! The appliances were top notch! It had an elegant Bohemian feel to it! Will definitely book in ..."

Reviewed on Aug 4, 2026

Pittsburgh House with Hot Tub, Patio & Free Parking!

Pittsburgh PA

2 min walk from Rex Theater

Book a stay at this family-friendly vacation home in Pittsburgh. Enjoy a garden, laundry facilities, and water skiing on site. Popular attractions PPG Paints ...

10/10 Exceptional! (8 reviews)

"My family loved the walkable neighborhood and the hot tub and the hours spent at nearby Kennywood Park!"

Reviewed on Aug 8, 2026

See all 2,018 properties in South Side

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.