Surfside Vacations from $321

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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!

The Latest Surfside vacation packages

Price found within the past 48 hours. Click for updated prices.
Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
Price was $505, price is now $321 per person
$321
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (471 reviews)
Clean and comfortable. Very easy to park.

Reviewed on Aug 5, 2025

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,068, price is now $622 per person
$622
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,679 reviews)
Property was nice and conveniently in Downtown Boston. The standard room is slightly small, but fine for a few day stay. Our TV did not work, the first time they sent someone to fix it and they unplugged it and plugged it back in. Which worked, however the TV would freeze every hour if not more still and we would have to do the same thing each time. Elevators are slow and there are no stairs to access the hotel rooms.

Reviewed on Aug 19, 2025

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Save 100% on your flight
Price was $837, price is now $499 per person
$499
per person
Oct 19 - Oct 23
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (158 reviews)
Great place. The staff were very friendly and helpful. Gave us a great tip for free access to a beautiful local beach. Clean room lovely swimming pool and beautiful breakfast

Reviewed on Aug 11, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,137, price is now $1,901 per person
$1,901
per person
Oct 20 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
Awesome hotel. Staff is great. Best hotel in Boston! And I've stayed at alot of em.

Reviewed on Aug 11, 2025

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Save 100% on your flight
Price was $802, price is now $499 per person
$499
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,101 reviews)
The bed is comfortable, bathrooms are always clean. The front desk was very kind.

Reviewed on Aug 16, 2025

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Discover the most popular places to visit in Surfside

Surfside Beach

Surfside Beach

4.5/5(57 reviews)

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

Surfside Beach
Madaket Beach

Madaket Beach

4.5/5(7 reviews)

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

4.5/5(25 reviews)

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

Jetties Beach

What to do in Surfside

Private Professional Photoshoot in Nantucket

Private Professional Photoshoot in Nantucket

$324
per adult
Private Professional Photoshoot in Nantucket
See all activities in Surfside

Surfside Hotel Deals

The Beachside

The Beachside

4 out of 5
30 North Beach Street, Nantucket, MA
$425 nightly
The price is $475 total per night from Sep 1 to Sep 2
$475 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (185 reviews)
"Everything was perfect. The room, the convenience to town, the movies on the lawn, the employees, everything was perfect."

Reviewed on Aug 18, 2025

The Beachside
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St., Nantucket, MA
$229 nightly
The price is $256 total per night from Sep 8 to Sep 9
$256 total
Sep 8 - Sep 9
Total includes taxes and fees
8.6/10 Excellent! (419 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
$158 nightly
The price is $176 total per night from Sep 10 to Sep 11
$176 total
Sep 10 - Sep 11
Total includes taxes and fees
8.8/10 Excellent! (540 reviews)
"Great accomodations, super friendly front desk personnel and very nice shuttle drivers!"

Reviewed on Aug 18, 2025

Nantucket Inn
See all 843 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.

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.

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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 $321 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.