Surfside Vacation Packages 2026 from $714

Surfside flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

$714

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

Boston Harbor Hotel

North End

Save 100% on your flight

$1,266

per person

Oct 23 - Oct 26

found 7 hours ago

Roundtrip non-stop flight included

Dallas (DAL) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Iris Hotel Boston

Coolidge Corner

Save 100% on your flight

$1,447

per person

Sep 23 - Sep 30

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

The Charles Hotel

West Cambridge

Save 100% on your flight

$1,756

per person

Oct 25 - Oct 31

found 2 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A full-service spa, 3 restaurants, and a 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

enVision Hotel Boston Everett

Save 100% on your flight

$1,069

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A gym is featured at this hotel, along with self parking. WiFi in public areas is free. Traveling for business? Take advantage of the business center, express check-in, and conference center.

Top Surfside hotels deals

Chill beach 3-bedroom getaway on Nobadeer beach

Nantucket MA

$1,010 nightly

$1,128 total

Aug 23 - Aug 24

Total with taxes and fees

This vacation home features laundry facilities.

Washer

Dryer

Nantucket Inn

1 Miller Lane Nantucket MA

$397 nightly

$443 total

Sep 7 - Sep 8

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 and free WiFi in public areas. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

Pool

Hot Tub

The Beachside

30 North Beach Street Nantucket MA

$590 nightly

$659 total

Sep 7 - Sep 8

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, a garden, and a picnic area are also on offer.

Pool

Pet friendly

Faraway Nantucket

29 Centre St. Nantucket MA

$413 nightly

$461 total

Sep 7 - Sep 8

Total with taxes and fees

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

White Elephant Hotel

50 Easton Street Nantucket MA

$1,295 nightly

$1,447 total

Sep 7 - Sep 8

Total with taxes and fees

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

Jared Coffin House

29 Broad Street Nantucket MA

$497 nightly

$555 total

Sep 2 - Sep 3

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

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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.

Frequently asked questions

How much are vacation packages to Surfside?

Treat yourself to an unforgettable experience in Surfside with a vacation package starting at $714. 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.