Surfside Vacations from $756

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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!

The Latest Surfside vacation packages

Price found within the past 48 hours. Click for updated prices.
Thomas Sea Suites
Boston Lodge and Suites
Luxury Apartments by Hyatus at Boston Everett
Furnished Apartment Near Longwood
The Coach House
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What to do in Surfside

Surfside Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
$656 nightly
The price is $733 total per night from Aug 11 to Aug 12
$733 total
Aug 11 - Aug 12
Total with taxes and fees
9.2/10 Wonderful! (740 reviews)
"Adorable, quaint place. Appreciated the shuttle. Staff at July 5 BBQ was awesome! However the check in staff was rude and definitely not helpful."

Reviewed on Jul 12, 2026

Nantucket Inn
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St. Nantucket MA
$611 nightly
The price is $683 total per night from Aug 12 to Aug 13
$683 total
Aug 12 - Aug 13
Total with taxes and fees
8.8/10 Excellent! (573 reviews)
"The room I got was relatively small for the price, but you do know that in advance. They have different bedding options. It was clean and air-conditioned and had everything you needed. My only complaint was dim lighting in the bathrooms, but otherwise it was a great stay."

Reviewed on Jul 10, 2026

Faraway Nantucket
The Beachside

The Beachside

4 out of 5
30 North Beach Street Nantucket MA
$746 nightly
The price is $834 total per night from Jul 20 to Jul 21
$834 total
Jul 20 - Jul 21
Total with taxes and fees
9.4/10 Exceptional! (307 reviews)
"Excellent venue, great location. Very clean"

Reviewed on Jul 6, 2026

The Beachside
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.

Find the Best Surfside Vacation Packages

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 0.2 miles (0.4 km) 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.

Surfside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Nantucket Memorial Airport (ACK)
Top Sights
Surfside Beach, Jetties Beach and Cisco Beach

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Frequently asked questions

How much does a Surfside vacation package cost?
You can snap up a vacation package to this top destination from $756 on Expedia. However, how much your vacation to Surfside costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Surfside?
If you're hoping to score a cheap Surfside vacation package, consider visiting in September, November and December. You'll generally find better prices on flights and hotels during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Surfside?
The ideal duration of your Surfside vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you time to tick off all the major attractions and discover some hidden spots along the way.
How to find the best Surfside package deals?
Begin your search for a Surfside package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Surfside package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Surfside escape off to a flying start.
Is it cheaper to book a Surfside vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights individually. Better still, you can tailor your Surfside trip to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Surfside?
If you've got your Surfside travel dates finalized, book as early as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Surfside vacation packages?
Set off on your perfect trip to Surfside with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or hold off until the next payday — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stick to your budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.