Surfside Holidays

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Top Flight + Hotel Deals in Surfside

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

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Located in a new neighborhood with lots of dining options and easy access to public transportation.

Reviewed on 28 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Great location. Easy access to the City.

Reviewed on 29 Jul 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on 28 Jul 2025

Surfside Beach Holiday

Whether you're heading off alone or with the whole family, it'll be easy to find rest and relaxation on your Surfside holiday. 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 centre, is a great choice for those who value convenience. Many travellers also lock in Surfside holiday packages closer to Nobadeer Beach, another excellent option.

Top hotels in Surfside

The Beachside

The Beachside

4 out of 5
30 North Beach Street, Nantucket, MA
9.2/10 Wonderful! (142 reviews)
"Nice"

Reviewed on 27 Jul 2025

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The Beachside
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St., Nantucket, MA
The price is €341 per night from 26 Aug to 27 Aug
€341
26 Aug - 27 Aug
includes taxes & fees
8.6/10 Excellent! (393 reviews)
"This hotel is stunning! The courtyard when you first walk in is surrounded by hydrangea’s in every color and the grounds are impeccable!! We stayed in the garden king room which was pie big for my husband and our 15 year old daughter. It’s also located right in the Herat of the island steps from ..."

Reviewed on 28 Jul 2025

Faraway Nantucket
Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane, Nantucket, MA
8.8/10 Excellent! (501 reviews)
"Beautiful would definitely stay again"

Reviewed on 26 Jul 2025

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Nantucket Inn
See all 842 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.

Popular places to visit

Madaket Beach

Madaket Beach

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

Madaket Beach
Siasconet Beach

Siasconet Beach

If a restful holiday is part of your travel plans, Siasconet Beach might be the perfect place to visit during your trip to Siasconset.

Siasconet Beach
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

What to do in Surfside

Exploring Nantucket's Main Street

Beyond the Cobblestones Self Guided Walking Tour of Nantucket

€9
per adult
Beyond the Cobblestones Self Guided Walking Tour of Nantucket
Nantucket Tirade Scavenger Hunt

Nutty Nantucket Scavenger Hunt

€25
per adult
Nutty Nantucket Scavenger Hunt
Private Professional Photoshoot in Nantucket

Private Professional Photoshoot in Nantucket

€289
per adult
Private Professional Photoshoot in Nantucket
See all activities in Surfside

Frequently asked questions

How much does a Surfside holiday package cost?
You can snap up a holiday package to this top destination from €546 on Expedia. However, how much your holiday 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 holiday 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 holiday. 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 holiday as a package?
An Expedia holiday 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 holiday 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 favourite season will help you decide when to go.
  2. Plan your budget wisely: As well as the cost of your accommodation, 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 holiday. 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 personalised Surfside holiday package.

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