Surfside Vacations from $586
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Boston Lodge and Suites
Dorchester
$586
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
What to do in Surfside
Private Vacation Photoshoot with Photographer in Nantucket
$624
per adult
Surfside Hotel Deals
Nantucket Inn
1 Miller Lane Nantucket MA
$367 nightly
$410 total
Oct 1 - Oct 2
Total with taxes and fees
9.2/10 Wonderful! (795 reviews)
"Extremely overpriced for what you receive. At nearly $900 per night, I expected a comfortable, upscale experience, but this felt more like a basic Hilton Garden Inn—without the convenience or hospitality. The beds squeaked, the bedding was incredibly thin and inexpensive, and we were freezing every ..."
Reviewed on Aug 30, 2026
The Beachside
30 North Beach Street Nantucket MA
$403 nightly
$450 total
Sep 28 - Sep 29
Total with taxes and fees
Faraway Nantucket
29 Centre St. Nantucket MA
$299 nightly
$334 total
Oct 1 - Oct 2
Total with taxes and fees
8.8/10 Excellent! (593 reviews)
"Way too expensive for what you get."
Reviewed on Aug 31, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Surfside vacation package cost?
You can snap up a vacation package to this top destination from $586 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.
