Surfside Vacations from $575

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.
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Price was $816, price is now $575 per person
$575
per person
May 22 - May 26
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8/10 Very Good! (259 reviews)
The staff were really nice and the food was good. They have an excellent location right on the beach.

Reviewed on Mar 12, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,068, price is now $1,454 per person
$1,454
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).

Reviewed on Apr 4, 2026

The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Price was $1,196, price is now $847 per person
$847
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (1,092 reviews)
Great hotel and location. Rooms were a bit old but excellent location and condition.

Reviewed on Apr 9, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,052, price is now $1,462 per person
$1,462
per person
Jun 11 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Fantastic hotel with beautiful waterfront rooms. Attention to details in the room were excellent. This is a true 5 star hotel.

Reviewed on Apr 10, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,993, price is now $1,421 per person
$1,421
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Everything advertised was correct and enjoyable relaxing.

Reviewed on Apr 11, 2026

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Discover the most popular places to visit in Surfside

AXE420 Sunbathers and dune landscape on Surfside Beach on the seaward coast of the island of Nantucket, Massachusetts, New England, USA

Surfside Beach

Why not spend a carefree afternoon at Surfside Beach during your travels in Nantucket? Discover the museums in this walkable area, or seek out its biking trails.

Surfside Beach
Siasconet Beach

Siasconet Beach

If a restful vacation is part of your travel plans, Siasconet Beach might be the perfect place to seek out during your trip to Siasconset.

Siasconet Beach
P5EH30 The Nantucket Atheneum, a historic public library in Nantucket, Massachusetts.

Nantucket Atheneum

Nantucket Atheneum is just one of the places to see in Nantucket, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the beautiful beaches.

Nantucket Atheneum

What to do in Surfside

Private Vacation Photoshoot with Photographer in Nantucket

Private Vacation Photoshoot with Photographer in Nantucket

$619
per adult
Private Vacation Photoshoot with Photographer in Nantucket
See all activities in Surfside

Surfside Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
$175 nightly
The price is $196 total per night from Apr 26 to Apr 27
$196 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (658 reviews)
Room was clean plenty parking no restaurant on site but the airport restaurant is close.

Reviewed on Apr 2, 2026

Nantucket Inn
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St. Nantucket MA
$161 nightly
The price is $179 total per night from Apr 12 to Apr 13
$179 total
Apr 12 - Apr 13
Total with taxes and fees
Faraway Nantucket
White Elephant Hotel

White Elephant Hotel

4.5 out of 5
50 Easton Street Nantucket MA
$229 nightly
The price is $256 total per night from Apr 26 to Apr 27
$256 total
Apr 26 - Apr 27
Total with taxes and fees
White Elephant Hotel
See all 1,164 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.

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 $575 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.