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.
DoubleTree Suites by Hilton Hotel Boston - Cambridge

DoubleTree Suites by Hilton Hotel Boston - Cambridge

4 out of 5
Allston
Price was CA $1,599, price is now CA $1,052 per person
CA $1,052
per person
May 16 - May 19
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,002 reviews)
Breakfast was amazing - rooms and showers excellent, their pool and hot tub was wonderful - one of the best stays at a hotel i’ve had in a very long time.

Reviewed on Apr 11, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,265, price is now CA $1,372 per person
CA $1,372
per person
May 24 - May 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
The rooms were very clean, beds were comfortable, staff friendly and great amenities (I wish the pool was open until 10 pm).

Reviewed on Apr 4, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,065, price is now CA $1,894 per person
CA $1,894
per person
May 24 - May 27
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
Classic luxury, a true five-star experience. Spectacular Boston Harbor views, top-notch staff, extra-comfortable bedding, rainfall shower.

Reviewed on Apr 12, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $2,674, price is now CA $1,753 per person
CA $1,753
per person
May 16 - May 21
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (253 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

Life House, Nantucket

Life House, Nantucket

3.5 out of 5
Nantucket Town
Price was CA $3,905, price is now CA $2,627 per person
CA $2,627
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (65 reviews)
The Life House was a very quiet, charming and friendly spot. Very much so a boutique hotel feel. The only thing that wasn’t ideal was the room we stayed in on the 3rd floor. Being over 6 feet, the room had slanted ceilings and a very tight doorway. It was very tight and not spacious unlike some of the other rooms I saw. Would definitely stay again but would make sure I don’t stay in that room again.

Reviewed on Sep 26, 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.

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Surfside Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
The price is CA $242 per night from Apr 26 to Apr 27
CA $242
CA $271 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (658 reviews)
Room was clean plenty parking no restaurant on site but the airport restaurant is close.

Reviewed on Apr 2, 2026

Nantucket Inn
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St. Nantucket MA
The price is CA $232 per night from Apr 16 to Apr 17
CA $232
CA $272 total
Apr 16 - Apr 17
includes taxes & fees
Faraway Nantucket
White Elephant Hotel

White Elephant Hotel

4.5 out of 5
50 Easton Street Nantucket MA
The price is CA $408 per night from Apr 27 to Apr 28
CA $408
CA $456 total
Apr 27 - Apr 28
includes taxes & fees
White Elephant Hotel
See all 1,168 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
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Family Vacations

Discover the most popular places to visit in Surfside

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
Nantucket_CiscoBeach_6297949-3

Cisco Beach

If a restful vacation is part of your travel plans, Cisco Beach might be the perfect place to seek out during your trip to Nantucket. Discover the museums in this walkable area, or seek out its biking trails.

Cisco Beach
D3RPKW Wooden steps leading down to Jetties beach, Nantucket Island, MA

Jetties Beach

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

Jetties Beach

What to do in Surfside

Nantucket Tirade Scavenger Hunt

Nutty Nantucket Scavenger Hunt

CA $40
per adult
Nutty Nantucket Scavenger Hunt
Private Vacation Photoshoot with Photographer in Nantucket

Private Vacation Photoshoot with Photographer in Nantucket

CA $850
per adult
Private Vacation Photoshoot with Photographer in Nantucket
See all activities in Surfside

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