The Pines Holidays from AU$2,189

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Your The Pines Holiday

The Pines is calling your name! Whatever type of adventure you're organising, you can see and experience the best of this neighbourhood with a The Pines holiday package. Some nearby attractions to see during your trip to The Pines include Rehoboth Beach Boardwalk, Tanger Outlets and Rehoboth Beach. No matter what your dream The Pines holiday looks like, you can turn it into reality with Expedia.

Top Holiday Package Deals in The Pines

Price found within the past 48 hours. Click for updated prices.
The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

2.5 out of 5
Price was AU$2,300, price is now AU$2,189 per person
AU$2,189
per person
20 July - 23 July
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
9.4/10 Exceptional! (179 reviews)
A quiet and clean gem set in the heart of Leonardtown in walking distance to shops and restaurants. Great breakfast area.

Reviewed on 31 May 2026

Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
Price was AU$3,335, price is now AU$3,090 per person
AU$3,090
per person
20 July - 23 July
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
9.8/10 Exceptional! (33 reviews)
Everything about the Swanendele Inn was exceptional: the location, the accommodations, the facilities, the decor, the hosts, and, not least, the breakfast. In fact, you could spend several days just exploring the remarkable antiques and artifacts around the place. However, what made the strongest impression was the fiery glow of dawn though the pine trees outside our balcony every morning in the Margeret Brent suite. Rhododaktylos, "The rosy-fingered dawn": I never understood the true meaning of that phrase until I saw that.

Reviewed on 4 Aug 2025

Solomons Island 6BR Family Getaway

Solomons Island 6BR Family Getaway

2 out of 5
Price was AU$3,464, price is now AU$3,259 per person
AU$3,259
per person
20 July - 23 July
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
No reviews
Boho Waterfront Getaway 5 Bedroom Retreat

Boho Waterfront Getaway 5 Bedroom Retreat

2 out of 5
Price was AU$3,352, price is now AU$3,159 per person
AU$3,159
per person
20 July - 23 July
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
No reviews
Spacious 6bed Woodland Retreat With Movie Room Deck

Spacious 6bed Woodland Retreat With Movie Room Deck

2 out of 5
Price was AU$3,503, price is now AU$3,327 per person
AU$3,327
per person
20 July - 23 July
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
No reviews

Our guide on where to stay in The Pines

Find the best The Pines areas and neighborhoods for the activities you enjoy most. Learn more about The Pines
A stretch along the sandy beach of Cape Henlopen State Park, Delaware taken at sunrise.

South Rehoboth

4 out of top 10 points of interest in this area

If you're spending some time in South Rehoboth, Funland and Silver Lake are top sights worth seeing.

Find hotels in South Rehoboth

Our pick of the best The Pines Hotel Deals

Henlopen Oceanfront Hotel

Henlopen Oceanfront Hotel

2 out of 5
511 North Boardwalk Rehoboth Beach DE
The price is AU$364 per night from 2 July to 3 July
AU$364
2 July - 3 July
includes taxes & fees
8.6/10 Excellent! (1,833 reviews)
"Great beach location!"

Reviewed on 18 June 2026

Henlopen Oceanfront Hotel
Hotel Bethany Beach

Hotel Bethany Beach

2.5 out of 5
39642 Jefferson Bridge Rd. Bethany Beach DE
Fully refundableReserve now, pay when you stay
The price is AU$339 per night from 1 July to 2 July
AU$339
1 July - 2 July
includes taxes & fees
9.2/10 Wonderful! (1,442 reviews)
"Housekeeping never came to do their job"

Reviewed on 18 June 2026

Hotel Bethany Beach
The Breakers Hotel & Suites

The Breakers Hotel & Suites

2.5 out of 5
105 Second Street Rehoboth Beach DE
The price is AU$369 per night from 1 July to 2 July
AU$369
1 July - 2 July
includes taxes & fees
8.8/10 Excellent! (1,808 reviews)
"Check in was difficult with not enough staff to clean the rooms. The shuttle to the beach was "not working" and we really relied on this to transport to the beach. The mattress for the sofa bed was covered in stains and the entire unit needs an update. It is hard to get into the soaker tub and it ..."

Reviewed on 18 June 2026

The Breakers Hotel & Suites
See all 8,049 properties in The Pines
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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Frequently asked questions

How much does a The Pines holiday package cost?
Our The Pines packages, which begin at just AU$2,189, are the easiest way to save loads of cash. Pick your preferred hotels, flights and more to create your ideal trip.
How do I get a cheap travel package to The Pines?
Imagine all the thrilling things you could do in The Pines with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and other bookings into a The Pines holiday package. You have loads of choice when it comes to booking with Expedia too. In fact, you can take your pick of more than 550 air carriers and 1 000 000 hotel options throughout the world. Whether you're holidaying with the entire family or going it alone, organising a getaway to The Pines is better with a package.
Where should I stay in The Pines?
With interesting attractions such as Rehoboth Beach Boardwalk and Rehoboth Beach in this area, try to find a hotel near them. Tanger Outlets is another sight that draws the crowds.
What are the top hotels in The Pines?
If it's your first visit to The Pines, make a reservation at Walk Everywhere - Perfect Condo In Downtown Rehoboth Beach or Two Bed, Two Bath Condo In Town. Both will make you feel at home and are top options with many travellers.
How far in advance should I book my The Pines holiday?
While prices change frequently, we generally advise booking your holiday as soon as possible. Many international fares become available on Expedia up to a year in advance. If you're booking last minute, you might still be lucky. Low prices to The Pines occasionally appear just weeks before departure.
What does an Expedia The Pines travel package include?
Flights, rental cars and hotels — we've got them well covered. With Expedia, you can shape your The Pines package however you want. All you have to do is work out what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger the savings!
What should I know before booking a The Pines travel package?
You can look forward to saving with an Expedia travel package. Bundle your airfares, rental cars and hotels and enjoy exciting discounts. You're not limited to hotels, however. We've got oceanfront condos, mountain cabins and just about everything in between!
Can I choose my airline with a The Pines Expedia holiday package?
Yes, definitely. Expedia has over 550 airline partners to pick from across the world. With so much choice, finding the perfect carrier to whisk you off to The Pines won't be hard.
If I'm not able to travel, can I cancel my The Pines holiday package?
Because we understand life is full of surprises, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've made your booking in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Stay near popular The Pines attractions

Grove Park

7.6/5 (113 reviews)
Grove Park is just one of the places to see in Rehoboth Beach, so why not enjoy the other things to explore during your travels? Wander through the beautiful beaches and seaside in this family-friendly area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.