Surfside Vacations

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Find the Best Surfside Vacation Packages

Surfside Hotel Deals

The Beachside

The Beachside

4 out of 5
30 North Beach Street, Nantucket, MA
The price is ₩504,315 per night from Sep 1 to Sep 2
₩504,315
₩591,490 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (187 reviews)
"It was absolutely fantastic"

Reviewed on Aug 19, 2025

The Beachside
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St., Nantucket, MA
The price is ₩280,175 per night from Sep 9 to Sep 10
₩280,175
₩328,603 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (425 reviews)
"loved my stay here! Perfect location!"

Reviewed on Aug 22, 2025

Faraway Nantucket
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane, Nantucket, MA
The price is ₩218,064 per night from Sep 21 to Sep 22
₩218,064
₩243,577 total
Sep 21 - Sep 22
includes taxes & fees
9/10 Wonderful! (546 reviews)
"Such good location and beautiful hotel, coffee shop and decor"

Reviewed on Aug 21, 2025

Nantucket Inn
See all 840 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.

Discover the most popular places to visit in Surfside

Sankaty Head Golf Club

Sankaty Head Golf Club

Enjoy a round of golf in Siasconset at Sankaty Head Golf Club. While you're in the area, stroll along the beautiful beaches.

Sankaty Head Golf Club

Tom Nevers Beach

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

Tom Nevers Beach

Frequently asked questions

How much does a Surfside vacation package cost?
You can snap up a vacation package to this top destination 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?
You can usually find reduced prices and better availability in January, February and March. Browse our cheap Surfside vacation packages and you could score some great off-season discounts.
How many days is enough for Surfside?
Usually, a handful of days is enough to check out the top attractions during your Surfside vacation. However, if you prefer to have time to kick back or go on day tours, consider extending your itinerary.
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.
How to plan a trip to Surfside?

  1. Choose your travel dates: What you'd like to do in Surfside and your favorite season will help you decide when to go.
  2. Plan your budget wisely: As well as the cost of your accommodations, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Surfside.
  3. Decide how long to go for: Now that you're up to speed on Surfside, you can figure out the right length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Surfside vacation package.

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