The Pines Vacation Packages

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Top Holiday Package Deals in The Pines

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
per person
Jul. 15 - Jul. 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
I really enjoyed my staying, the only thing it didn't work was my room's phone to call the main lobby. Other than that was good.

Reviewed on May 24, 2024

Roomza Inner Harbor at Lord Baltimore

Roomza Inner Harbor at Lord Baltimore

2 out of 5
Downtown Baltimore
per person
Jul. 15 - Jul. 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (6 reviews)
Roomza has hands down the best staff of any hotel. They are friendly, helpful, and attentive. An added bonus to my stay was free drinks and local snacks. I'm now addicted to the Berger's cookies and Utz Crab Chips! If having the most up to date bathroom is important to you, then maybe you wouldn't like Roomza as the bathroom tile was a bit outdated, but in my mind that was much outweighed by the cleanliness. The main room area was large and modern. This is my new go-to hotel when I travel to Baltimore.

Reviewed on May 24, 2024

Graduate Annapolis

Graduate Annapolis

4 out of 5
per person
Jul. 15 - Jul. 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,048 reviews)
Very attractive hotel. All staff helpful. Breakfast cafe good and quick. Bed comfortable. Quiet.

Reviewed on May 26, 2024

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
per person
Jul. 15 - Jul. 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (1,612 reviews)
Myra at checkin was great!!!

Reviewed on May 25, 2024

Hotel Indigo Baltimore Downtown, an IHG Hotel

Hotel Indigo Baltimore Downtown, an IHG Hotel

4 out of 5
Mount Vernon
per person
Jul. 15 - Jul. 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.2/10 Wonderful! (1,005 reviews)
The staff was very nice and helpful. The food was really good.

Reviewed on May 23, 2024

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
Rehoboth Beach showing a sandy beach

South Rehoboth

2 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 hotel + flight trips in South Rehoboth

The Pines Hotel Deals

La Mer Beachfront Resort
La Mer Beachfront Resort
3.5 out of 5
1317 Beach Avenue, Cape May, NJ
The price is CA $301 per night from Jun. 2 to Jun. 3
CA $301
CA $345 total
includes taxes & fees
Jun 2 - Jun 3
9/10 Wonderful! (1,011 reviews)
Beautiful place!
"The parking was free. The cost was a bit high but expected. The text msgs throughout the weekend to suggest and offer activities and dining were awesome."

Reviewed on May 25, 2024

La Mer Beachfront Resort
Henlopen Hotel
Henlopen Hotel
2 out of 5
511 North Boardwalk, Rehoboth Beach, DE
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from May 29 to May 30
CA $135
CA $150 total
includes taxes & fees
May 29 - May 30
8.2/10 Very Good! (1,006 reviews)
Amazing Experience!!!
"I have to say that from check in to check out my stay here was amazing! The front desk clerk at check in was friendly, funny and went out of her way to explain the process to me because I had to book one night on Hotels.COM and one night directly through the hotel because of plans changing. Every ..."

Reviewed on May 24, 2024

Henlopen Hotel
The Breakers Hotel & Suites
The Breakers Hotel & Suites
2.5 out of 5
105 Second Street, Rehoboth Beach, DE
The price is CA $197 per night from May 27 to May 28
CA $197
CA $221 total
includes taxes & fees
May 27 - May 28
8.8/10 Excellent! (1,877 reviews)
"The rooms and property were well taken care of. The staff was friendly and helpful. The breakfast was good."

Reviewed on May 24, 2024

The Breakers Hotel & Suites
See all 6,756 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

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Family Vacations

Frequently asked questions

How much does a The Pines vacation package cost?
Our The Pines packages, which begin at just CA $687, 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 vacation 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 vacationing with the entire family or going it alone, organizing 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 travelers.
How far in advance should I book my The Pines vacation?
While prices change frequently, we generally advise booking your vacation 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 vacation 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 vacation 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.

Discover the most popular places to visit in The Pines

Image for Rehoboth Beach Boardwalk

Rehoboth Beach Boardwalk

4/5(5 reviews)

After visiting Rehoboth Beach Boardwalk, make a plan to see the other sights and activities in Rehoboth Beach. Check out the shops and top-notch restaurants in this walkable area.

Rehoboth Beach Boardwalk
Image for Rehoboth Beach

Rehoboth Beach

Why not spend a lazy afternoon at Rehoboth Beach during your trip to Rehoboth Beach? Check out the shops and top-notch restaurants in this walkable area.

Rehoboth Beach
Image for Indian River Life-Saving Station Museum

Indian River Life-Saving Station Museum

You can enjoy some culture when you stop by Indian River Life-Saving Station Museum in Rehoboth Beach. Wander the beautiful beaches and seaside in this family-friendly area.

Indian River Life-Saving Station Museum

Things to do

Image for Jet Ski Rentals in Dewey Beach

Jet Ski Rentals in Dewey Beach

CA $156
Per adult
Jet Ski Rentals in Dewey Beach
See all activities in Rehoboth Beach

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.