Surfside Vacations from $326

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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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $575, price is now $326 per person
$326
per person
Feb 7 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
19.6/10 Exceptional! (1,005 reviews)
Everywhere you went you were greeted with a smile. The front desk were wonderful. The doorman and bellman were very attentive. The room itself was very spacious and well appointed. I was thrilled to have access to Diptique beauty products. It was a fabulous stay from start to finish.

Reviewed on Nov 24, 2025

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $1,116, price is now $627 per person
$627
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
17.2/10 Exceptional! (1,337 reviews)
Very clean room. It’s old hotel so rooms are small but didn’t bother us . Carlos was very nice at check in

Reviewed on Nov 25, 2025

The Chester Hotel

The Chester Hotel

4 out of 5
South End
Save 100% on your flight
Price was $1,295, price is now $746 per person
$746
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
17.2/10 Exceptional! (27 reviews)
The kitchen was fully equipped, and the place was very clean. It's conveniently located near universities and downtown, with everything within walking distance. However, I do wish there was an elevator—carrying luggage up to the fourth floor was quite a challenge. That said, the bed and sofa couch were comfortable, and we slept well.

Reviewed on Nov 11, 2025

Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
Newton Corner
Price was $698, price is now $403 per person
$403
per person
Feb 5 - Feb 10
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
16.8/10 Exceptional! (2,907 reviews)
Was in room 624 had plumbing problems. The water would not go down the drain too easily in the sink and in the bathtub the wash the wash would look like our back of something and the toilet would not wash OK in the first one the language barrier came in when I had a removed from the first one to the second one 524 I’m sorry 503 from 624 so the room needs some improvement and visibility of towels needs improvement tool

Reviewed on Nov 26, 2025

The Liberty, a Marriott Luxury Collection Hotel, Boston

The Liberty, a Marriott Luxury Collection Hotel, Boston

5 out of 5
West End
Save 100% on your flight
Price was $862, price is now $500 per person
$500
per person
Feb 5 - Feb 9
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
17.6/10 Exceptional! (1,005 reviews)
Staff was super friendly and welcoming.

Reviewed on Nov 23, 2025

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Discover the most popular places to visit in Surfside

Surfside Beach

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
Jetties Beach

Jetties Beach

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

Jetties Beach
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

What to do in Surfside

Private Professional Photoshoot in Nantucket

Private Professional Photoshoot in Nantucket

$322
per adult
Private Professional Photoshoot in Nantucket
See all activities in Surfside

Surfside Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
$161 nightly
The price is $180 total per night from Dec 14 to Dec 15
$180 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (621 reviews)
Lovely stay!

Reviewed on Nov 18, 2025

Nantucket Inn
Hotel Pippa

Hotel Pippa

3.5 out of 5
5 Chestnut Street Nantucket MA
$176 nightly
The price is $197 total per night from Nov 30 to Dec 1
$197 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (253 reviews)
Convenient and clean. Very cool design sense.

Reviewed on Oct 29, 2025

Hotel Pippa
White Elephant Hotel

White Elephant Hotel

4.5 out of 5
50 Easton Street Nantucket MA
$395 nightly
The price is $441 total per night from Nov 30 to Dec 1
$441 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (334 reviews)
Great room great staff!

Reviewed on Nov 9, 2025

White Elephant Hotel
See all 970 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 $326 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.