Deals on vacations and trips to Surfside

Save when you book Surfside package deals

Choose two or more items and save on your trip:

Top Surfside hotels deals

Nantucket Inn

Nantucket Inn

3.5 out of 5
1 Miller Lane Nantucket MA
$126 nightly
The price is $141 total per night
$141 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.
Pool
Hot Tub
Jared Coffin House

Jared Coffin House

4 out of 5
29 Broad Street Nantucket MA
$167 nightly
The price is $187 total per night
$187 total
Dec 29 - Dec 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Breakfast included
Parking included
Nantucket Resort Collection

Nantucket Resort Collection

4 out of 5
3 Step Lane Nantucket MA
$129 nightly
The price is $144 total per night
$144 total
Dec 23 - Dec 24
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and luggage storage are also on offer.
Breakfast included
Pet friendly
White Elephant Hotel

White Elephant Hotel

4.5 out of 5
50 Easton Street Nantucket MA
Get rates
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking and a free beach shuttle.
Pool
Spa
Hotel Pippa

Hotel Pippa

3.5 out of 5
5 Chestnut Street Nantucket MA
$163 nightly
The price is $182 total per night
$182 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel features a bar/lounge, free WiFi in public areas, and a terrace. Enjoy the free continental breakfast each morning. Dry cleaning, luggage storage, and concierge services are also on offer.
Breakfast included
Free WiFi
Faraway Nantucket

Faraway Nantucket

3.5 out of 5
29 Centre St. Nantucket MA
Get rates
Free WiFi in public areas, a terrace, and a garden are available at this hotel. Express check-in, express check-out, and luggage storage are also on offer.
Pet friendly
Free WiFi
Don't see what you're looking for?
See all available properties in Surfside
View all properties
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

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
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
Jetties Beach

Jetties Beach

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

Jetties Beach

Frequently asked questions

How much are vacation packages to Surfside?
Treat yourself to an unforgettable experience in Surfside with a vacation package starting at . Locking in hotels, flights and tours with Travelocity is simple. And even better, our package deals will leave you with more cash in your pocket for plenty of fun times.
Where can I get the best vacation package deals for Surfside?
Travelocity will be able to help you snag a great Surfside package deal. With as many as 400 airlines and 1,000,000 properties worldwide, there's no doubt you'll be able to craft the perfect itinerary.
Why should I purchase my Surfside vacation package via Travelocity?
The three S's — savings, support and a stress-free booking — are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you can relax knowing you'll always get the best deal available.
Can I save money on my Surfside car rental if I book it with hotels and flights?
Booking a Surfside vacation package with Travelocity is a surefire way to save your hard-earned cash. You can bundle a hotel, flight and car, or any combination of them, and land awesome discounts. You might also like to throw in some activities and experiences. Once you've collected the keys to the rental car, head out of the neighborhood and see what this place has to offer. Around 90 mi from Surfside, Fenway Park is the ideal road trip.

Photos of local treasures

Browse Surfside vacation photos for more inspiration

Surfside