
Henlopen Keys Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 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
Plan, book, and manage your trip all in one place
Top Holiday Package Deals in Henlopen Keys
Price found within the past 48 hours. Click for updated prices.


Sagamore Pendry Baltimore
Fells Point
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip flight included
Calgary (YYC) to Baltimore (BWI)
9.4/10 Exceptional! (1,009 reviews)
Staying at the Sagamore Pendry had been on my bucket list for years, and I finally made it happen for a special anniversary. The hotel is undeniably elegant, with exceptional staff and a clean, well-maintained atmosphere that reflects its historic charm. However, I couldn’t help but feel underwhelmed given the premium price point. There are several other hotels in the area offering comparable quality at a significantly lower cost. While the Pendry delivers a solid experience, it felt more like paying for a name than indulging in true luxury. I’m glad I checked it off my list, but I wouldn’t return—especially when value and experience don’t quite align.
Reviewed on Aug. 14, 2025

DoubleTree by Hilton Hotel Largo/Washington DC
per person
Sep 20 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
7.8/10 Good! (1,007 reviews)
The Largo Doubletree Hotel by Hilton was a pleasant venue. There was a mix-up with my reservation that was made resolute by the Manager on duty, Ms. Nordia. The entire hotel staff was courteous, kind, professional and helpful. The room colors and accommodations were tasteful. The dining room options for breakfast and lunch/dinner were great choices and enjoyable. The short summer getaway at this location was a good experience.
Reviewed on Aug. 14, 2025

Sheraton Baltimore North Hotel
per person
Nov 7 - Nov 10
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
This is a very nice hotel and was located in an area that was very convenient. It was clean and very comfortable. I highly recommend staying here
Reviewed on Aug. 12, 2025

The Ivy Hotel
Midtown
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip flight included
Calgary (YYC) to Baltimore (BWI)
10/10 Exceptional! (181 reviews)
My husband and I travel all around the world. We decided to celebrate his milestone birthday and retirement at The Ivy, which had been on our bucket list for a while. My goodness! It's the best hotel we've ever visited. If there were such a thing as a six star hotel, this would be it. The rooms, the luxurious touches, the service, the thoughtful design, the food, the ammenities--all perfection. No detail was overlooked. Everyone on the staff greeted us by name. Their car service was able to take us anywhere witinin a 3-mile radius, so we were able to valet park on arrival and not have to drive anywhere ourselves until we left. They have a no tipping policy. The room is stocked with wine, coffee, tea, local beers, sparkling water, etc. (all complimentary). They anticipated our needs and made our stay magical. We hope to return soon. Shout out to our servers, Anthony, April, and Jackie; our driver Chris; our consierge James. Well done one and all.
Reviewed on Jul. 7, 2025
Where to stay in Henlopen Keys
Find the best Henlopen Keys areas and neighborhoods for the activities you enjoy most. Learn more about Henlopen Keys

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.
Henlopen Keys Hotel Deals

Henlopen Oceanfront Hotel
511 North Boardwalk, Rehoboth Beach, DE
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Sep 1 to Sep 2
CA $275
CA $305 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,592 reviews)
"Great location"
Reviewed on Aug. 16, 2025

Staybridge Suites Rehoboth Beach by IHG
34521 Old Postal Lane, Rehoboth Beach, DE
Fully refundable
The price is CA $163 per night from Sep 2 to Sep 3
CA $163
CA $181 total
Sep 2 - Sep 3
includes taxes & fees
9.4/10 Exceptional! (221 reviews)
"New"
Reviewed on Aug. 14, 2025

La Mer Beachfront Resort
1317 Beach Avenue, Cape May, NJ
The price is CA $364 per night from Sep 14 to Sep 15
CA $364
CA $418 total
Sep 14 - Sep 15
includes taxes & fees
9/10 Wonderful! (1,122 reviews)
"Great resort for a clean and quiet stay."
Reviewed on Aug. 13, 2025
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.
Discover the most popular places to visit in Henlopen Keys
Tanger Outlets
You can enjoy retail therapy at Tanger Outlets during your trip to Rehoboth Beach. Amble around this family-friendly area's beautiful beaches and enjoy its lively bars.
Jungle Jim's River Safari Water Park
Bring the family to Jungle Jim's River Safari Water Park and enjoy this exciting amusement park in Rehoboth Beach. Stroll along the seaside in this family-friendly area, or check out its lively bars.
Things to do
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.