Whaleyville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Whaleyville Vacation

Get ready to experience Whaleyville on your terms with a custom Whaleyville vacation package! Discovering the treasures of this interesting city is simpler with a base in a neighborhood such as Glen Riddle, which is good for golfing, among plenty of other things. If taking in sights is on the cards during your trip to Whaleyville, stop by popular attractions like The Bay Club, Bay Club Golf Course and Globe Theater. A few quick clicks is all it takes to create the ideal Whaleyville vacation on Expedia.

Top Whaleyville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
Price was CA $1,268, price is now CA $1,190 per person
CA $1,190
per person
Jan 17 - Jan 23
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Salisbury (SBY)
8.6/10 Excellent! (990 reviews)
Convenient location, friendly staff, clean

Reviewed on Nov 8, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was CA $1,537, price is now CA $1,280 per person
CA $1,280
per person
Dec 27 - Jan 3
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (3,964 reviews)
No breakfast, exoust

Reviewed on Nov 11, 2026

Comfort Inn Gold Coast

Comfort Inn Gold Coast

2.5 out of 5
North Ocean City
Price was CA $1,390, price is now CA $1,272 per person
CA $1,272
per person
Dec 27 - Jan 3
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very good! (1,003 reviews)

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
Price was CA $1,450, price is now CA $1,363 per person
CA $1,363
per person
Dec 13 - Dec 19
found 17 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Salisbury (SBY)
7.2/10 Good! (511 reviews)

Ready to book your vacation to Whaleyville?

 

Choose your dates

Whaleyville Hotel Deals

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

3 out of 5
1701 Atlantic Avenue Ocean City MD
Fully refundable
The price is CA $128 per night from Dec 10 to Dec 11
CA $128
CA $143 total
Dec 10 - Dec 11
includes taxes & fees
Holiday Inn & Suites Ocean City by IHG
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
The price is CA $121 per night from Nov 17 to Nov 18
CA $121
CA $158 total
Nov 17 - Nov 18
includes taxes & fees
Princess Royale Oceanfront Resort
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
The price is CA $76 per night from Nov 18 to Nov 19
CA $76
CA $85 total
Nov 18 - Nov 19
includes taxes & fees
9/10 Wonderful! (4,013 reviews)
"No breakfast, exoust"

Reviewed on Nov 11, 2026

Grand Hotel Ocean City Oceanfront
See all 9,349 properties in Whaleyville
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Whaleyville vacation package cost?
You'll find cheap prices from CA $1,190 on Expedia for your Whaleyville escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Whaleyville costs.
What are the cheapest months to go to Whaleyville?
If you're hoping to book a cheap Whaleyville vacation package, consider planning a trip in January, February and November. You'll typically find lower rates on flights and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Whaleyville?
For a Whaleyville vacation, a few days will be enough to tour the highlights. Be sure to check out Bay Club Golf Course — it's one of the major sights in this destination. If you're looking for more activities, think about basing yourself here and setting off on some day trips from Whaleyville.
How to find the best Whaleyville package deals?
Begin your search for a Whaleyville package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Whaleyville package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Whaleyville adventure underway.
Is it cheaper to book a Whaleyville vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging accommodations and flights individually. Better still, you can personalize your Whaleyville trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Whaleyville?
If you're considering a spur-of-the-moment Whaleyville trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Whaleyville?

  1. Pick your travel dates: The things you'd like to do in Whaleyville and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Whaleyville.
  3. Decide how long to go for: Now that you're more familiar with Whaleyville, you can work out the right length of your vacation. Pull together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Whaleyville vacation package.

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