Surfside Vacation Packages

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Your Surfside Vacation

Put together a custom vacation package to Surfside and prepare to experience this fascinating city however you like. Consider spending time in the neighborhood of Madequecham, which is good for coastal beaches and more. Make your trip to Surfside even more enjoyable by going sightseeing. Surfside Beach, Jetties Beach and Cisco Beach are among the top attractions worth exploring. Stop dreaming and start doing. Explore the multitude of options on Expedia today and finally put your Surfside vacation plans into motion!

Top Surfside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was CA $1,644, price is now CA $1,138 per person
CA $1,138
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9/10 Wonderful! (3,501 reviews)
I don't normally submit reviews but felt compelled to for this hotel - Just stayed for 2 nights for a quick weekend trip to Boston - Positives were the staff were all very helpful and friendly, the hotel was clean and convenient to most attractions and sites . However photos look better online than the hotel actually is especially for the money - Furnishings were old- baths were old and very basic with extremely small shower. Carpet and furniture were worn overall for the price the hotel is underwhelming with very few amenities - Can find a nicer hotel for same or a little more money - overall disappointing.

Reviewed on Nov 9, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,415, price is now CA $2,164 per person
CA $2,164
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $1,975, price is now CA $1,259 per person
CA $1,259
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)
By far one of the worst hotels I have stayed in.

Reviewed on Nov 9, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,397, price is now CA $1,548 per person
CA $1,548
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)
The best location and the beat service! The best swimming pool

Reviewed on Nov 9, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was CA $2,234, price is now CA $1,488 per person
CA $1,488
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Amazing hotel Great rooms and helpful, professional staff. Couldn’t fault it.

Reviewed on Nov 8, 2026

Surfside Beach Vacation

Whether you're heading off alone or with the whole family, it'll be easy to find rest and relaxation on your Surfside vacation. Search for pretty seashells or sit by the shore and listen to the waves. Whatever you decide to do, your trip to Surfside will certainly be unforgettable. Surfside Beach, located 0.32 kilometres from the town center, is a great choice for those who value convenience. Many travelers also lock in Surfside vacation packages closer to Nobadeer Beach, another excellent option.

Ready to book your vacation to Surfside?

 

Choose your dates

Surfside Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
The price is CA $174 per night from Nov 24 to Nov 25
CA $174
CA $195 total
Nov 24 - Nov 25
includes taxes & fees
Nantucket Inn
The Beachside

The Beachside

4 out of 5
30 North Beach Street Nantucket MA
The price is CA $278 per night from Dec 6 to Dec 7
CA $278
CA $332 total
Dec 6 - Dec 7
includes taxes & fees
9.4/10 Exceptional! (407 reviews)
"Will definitely return for my next stay on the island."

Reviewed on Nov 6, 2026

The Beachside
Faraway Nantucket

Faraway Nantucket

4 out of 5
29 Centre St. Nantucket MA
The price is CA $233 per night from Dec 6 to Dec 7
CA $233
CA $273 total
Dec 6 - Dec 7
includes taxes & fees
8.8/10 Excellent! (638 reviews)
"Fantastic overnight stay for our November getaway ❤️"

Reviewed on Nov 8, 2026

Faraway Nantucket
See all 810 properties in Surfside
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
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What to do in Surfside

Nutty Nantucket Scavenger Hunt

Nutty Nantucket Scavenger Hunt

CA $41
per adult
Nutty Nantucket Scavenger Hunt
See all activities in Surfside

Frequently asked questions

How much does a Surfside vacation package cost?
You'll find cheap prices from CA $1,138 on Expedia for your Surfside getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Surfside costs.
What are the cheapest months to go to Surfside?
If you'd like to score a cheap Surfside vacation package, consider planning a trip in January, February and March. You'll typically find lower rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Surfside?
Dedicate at least 4 days for your Surfside vacation if you want to enjoy everything that makes this place unique. Wander around key areas, including Nantucket Town and Brant Point. Then check out top sights like Madaket Beach and Whaling Museum. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Surfside? Consider fitting in an excursion or two.
How to find the best Surfside package deals?
Start your search for a Surfside package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Surfside package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Surfside escape underway.
Is it cheaper to book a Surfside vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still have the freedom to create a customized Surfside vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Surfside?
If you've got your Surfside travel dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Surfside?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Surfside.
  2. Budget wisely: As well as the cost of your hotel, you should consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Surfside.
  3. Decide how long to go away for: Now that you're up to speed on Surfside, you can work out the right length of your vacation. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: Once you've settled on your dates and duration, book the ideal Surfside vacation package for you.

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