Surfside Vacations from ￥292,318

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The Latest Surfside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Boston

Hyatt Regency Boston

4 out of 5
Downtown Boston
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (1,576 reviews)
Very good service from the check-in to the check-out. Staff were really nice.

Reviewed on Aug 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on Aug 5, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (360 reviews)
The property wasn’t at the level we expected of the Mandarin Oriental, however the location was good and walkable to Bay Bay restaurants and shopping.

Reviewed on Aug 4, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,005 reviews)
Very convenient boutique hotel

Reviewed on Aug 5, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,014 reviews)
Wonderful high end hotel in a fantastic area. Loved being able to walk to the north end!

Reviewed on Aug 3, 2025

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 0.32 kilometers 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 Hotel Deals

The Beachside

The Beachside

4 out of 5
30 North Beach Street, Nantucket, MA
9.2/10 Wonderful! (162 reviews)
"Simple, clean elegant"

Reviewed on Aug 6, 2025

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The Beachside
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St., Nantucket, MA
The price is ￥32,390 per night from Sep 8 to Sep 9
￥32,390
￥37,988 total
Sep 8 - Sep 9
includes taxes & fees
8.6/10 Excellent! (410 reviews)
"Great location"

Reviewed on Aug 7, 2025

Faraway Nantucket
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane, Nantucket, MA
8.8/10 Excellent! (522 reviews)
"The resort room we had a leak from ceiling in our bathroom. They quickly changed room and replaced damaged items and gave us free breakfast. We were happy with the corrections and would stay again. Claira at front desk was very friendly. The property was clean and food was good."

Reviewed on Aug 5, 2025

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Nantucket Inn
See all 841 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

Nantucket Atheneum

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

Brant Point Light

Find out about the history of Nantucket when you take a trip to Brant Point Light. While you're in the area, stroll along the beautiful beaches.

Brant Point Light

What to do in Surfside

Private Nantucket Beach Fishing Activity with a Guide

Private Nantucket Beach Fishing Activity with a Guide

￥92,306
per traveler
Private Nantucket Beach Fishing Activity with a Guide
See all activities in Surfside

Frequently asked questions

How much does a Surfside vacation package cost?
You can snap up a vacation package to this top destination from ￥292,318 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.