Surfside Vacation Packages

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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!

Top Surfside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,008, price is now CA $536 per person
CA $536
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,757, price is now CA $2,165 per person
CA $2,165
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on Aug. 20, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Price was CA $2,417, price is now CA $1,572 per person
CA $1,572
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (139 reviews)
Clean. Great location.

Reviewed on Jul. 31, 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was CA $2,161, price is now CA $1,430 per person
CA $1,430
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Heather was unbelievable in every way. Because of her past excellent service we returned!! She makes this hotel experience a true pleasure. Thank you Heather for your kind and gracious assistance.

Reviewed on Aug. 21, 2025

DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,455, price is now CA $967 per person
CA $967
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (1,002 reviews)
Great Experience at a great location

Reviewed on Aug. 21, 2025

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 kilometres 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.

Ready to book your vacation to Surfside?

 

Choose your dates

Surfside Hotel Deals

The Beachside

The Beachside

4 out of 5
30 North Beach Street, Nantucket, MA
The price is CA $507 per night from Sep 1 to Sep 2
CA $507
CA $594 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 CA $276 per night from Sep 9 to Sep 10
CA $276
CA $324 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (422 reviews)
August in Nantucket
"We loved the hotel, the courtyard, and the proximity to all of Nantucket. It was an amazing location, with great rooms, great service, and a wonderful bar, restaurant, and lounge. All of the employees were wonderful as well. I would highly recommend it to anyone."

Reviewed on Aug. 12, 2025

Faraway Nantucket
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane, Nantucket, MA
The price is CA $373 per night from Sep 7 to Sep 8
CA $373
CA $417 total
Sep 7 - Sep 8
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Surfside

Madaket Beach

Madaket Beach

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

Madaket Beach
Jetties Beach

Jetties Beach

4/5(1 review)

Why not spend a carefree afternoon at Jetties Beach during your travels in Nantucket?

Jetties 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

What to do in Surfside

Private Professional Photoshoot in Nantucket

Private Professional Photoshoot in Nantucket

CA $449
per adult
Private Professional Photoshoot in Nantucket
See all activities in Surfside

Frequently asked questions

How much does a Surfside vacation package cost?
You'll find cheap prices from CA $536 on Expedia for your Surfside getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Surfside costs.
What are the cheapest months to go to Surfside?
If you'd like to score a cheap Surfside vacation package, consider planning a trip in January, February and March. You'll typically find lower rates on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Surfside?
Dedicate at least 4 days for your Surfside vacation if you want to enjoy everything that makes this place unique. Wander around key areas, including Nantucket Town and Brant Point. Then check out top sights like Madaket Beach and Whaling Museum. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Surfside? Consider fitting in an excursion or two.
How to find the best Surfside package deals?
Start your search for a Surfside package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Surfside package deal straight away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Surfside escape underway.
Is it cheaper to book a Surfside vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still have the freedom to create a customized Surfside vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Surfside?
If you've got your Surfside travel dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Surfside?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Surfside.
  2. Budget wisely: As well as the cost of your hotel, you should consider other expenses. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Surfside.
  3. Decide how long to go away for: Now that you're up to speed on Surfside, you can work out the right length of your vacation. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your airfare and accommodations: Once you've settled on your dates and duration, book the ideal Surfside vacation package for you.

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