Surfside Vacations from $746
Book a Hotel + Flight or Car together to unlock savings
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
$746
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more.
We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of.
Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.
Reviewed on Oct 17, 2026
Four Seasons Hotel Boston
Bay Village
$1,145
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (487 reviews)
For the most high end hotel in Boston, lacked updated amenities that other newer hotels have. Rooms were severely dated.
Reviewed on Oct 20, 2026
The Langham, Boston
Downtown Boston
$756
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Staff member Nelson was very nice and provided excellent customer service on the 8th floor. I truly appreciated their kindness, professionalism, and helpful attitude. Thank you, Nelson, for making my experience a positive one!
Reviewed on Oct 21, 2026
Surfside Hotel Deals
Nantucket Inn
1 Miller Lane Nantucket MA
$134 nightly
$150 total
Nov 20 - Nov 21
Total with taxes and fees
9.2/10 Wonderful! (843 reviews)
"Although the room was modern I was disappointed it was not exactly clean. The wooden stairs to our 2nd level room was like the saying goes “slippery when wet” The staff was very helpful and pleasant. The shuttle service was very convenient."
Reviewed on Oct 19, 2026
The Beachside
30 North Beach Street Nantucket MA
$192 nightly
$214 total
Nov 1 - Nov 2
Total with taxes and fees
Faraway Nantucket
29 Centre St. Nantucket MA
$187 nightly
$209 total
Oct 28 - Oct 29
Total with taxes and fees
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 $746 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.