Surfside Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Surfside Holiday

Our pick of the best Surfside Hotel Deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
The price is NZ$248 per night from 19 Mar to 20 Mar
NZ$248
19 Mar - 20 Mar
includes taxes & fees
9/10 Wonderful! (652 reviews)
The staff was friendly. Clean rooms. We arrived in February (offseason) and they do close at 7pm. Reopen at 9am. If arriving outside of that time be sure and call ahead

Reviewed on 6 Feb 2026

Nantucket Inn
Nantucket Resort Collection

Nantucket Resort Collection

4 out of 5
3 Step Lane Nantucket MA
The price is NZ$257 per night from 19 Mar to 20 Mar
NZ$257
19 Mar - 20 Mar
includes taxes & fees
9/10 Wonderful! (375 reviews)
yes!

Reviewed on 5 Jan 2026

Nantucket Resort Collection
Hotel Pippa

Hotel Pippa

3.5 out of 5
5 Chestnut Street Nantucket MA
The price is NZ$265 per night from 18 Feb to 19 Feb
NZ$265
18 Feb - 19 Feb
includes taxes & fees
9.2/10 Wonderful! (262 reviews)
Charming renovation of a historic house. Our host Sydney was delightful.

Reviewed on 17 Jan 2026

Hotel Pippa
See all 1,165 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.

Discover the most popular places to visit in Surfside

Walk through the front yard of expensive ocean front properties during the bluff walk.

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
Nantucket_CiscoBeach_6297949-3

Cisco Beach

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

Cisco Beach
Nantucket_NobadeerBeach_6287514-6

Nobadeer Beach

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

Nobadeer Beach

Explore a world of travel with Expedia

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