Osterville Vacation Packages 2026 from $536

Osterville flight + hotel vacation packages

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

Cape Cod Hotel

$536

per person

Jun 8 - Jun 13

found 24 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hyannis (HYA)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the sauna and free perks like buffet breakfast and free self parking.

Anchor In Distinctive Waterfront Lodging

$821

per person

Jul 16 - Jul 19

found 21 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hyannis (HYA)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a snack bar/deli are also on offer.

Holiday Inn Hyannis by IHG

$729

per person

Jun 8 - Jun 13

found 24 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hyannis (HYA)

This hotel features an outdoor pool, an indoor pool, and a restaurant. Enjoy the gym and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Margaritaville Resort Cape Cod

$1,003

per person

Jun 8 - Jun 12

found 16 hours ago

Roundtrip flight included

Harrisburg (MDT) to Hyannis (HYA)

This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.

Hyannis Plaza Hotel

$613

per person

Jun 8 - Jun 13

found 24 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Hyannis (HYA)

An outdoor pool is featured at this hotel, along with free self parking. There's a garden and multilingual staff can provide around-the-clock assistance.

Top Osterville hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$202 total

May 3 - May 4

Total with taxes and fees

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$137 total

Apr 28 - Apr 29

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$138 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features 2 poolside bars, 2 bars/lounges, and an indoor pool. Enjoy the gym and free perks like buffet breakfast and free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$138 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Falmouth Inn

824 Main Street Falmouth MA

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$131 total

Apr 28 - Apr 29

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. 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.

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

Free Cancellation

Reserve now, pay when you stay

$185 nightly

$212 total

Apr 29 - Apr 30

Total with taxes and fees

A private beach, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the picnic area.

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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.

Popular places to visit

Dowses Beach

Why not spend a lazy afternoon at Dowses Beach during your trip to Osterville?

Fluffy clouds and blue sky over the Occupy Chatham public shack on Chatham South Beach

Public Beach

Why not spend a lazy afternoon at Public Beach during your trip to Osterville?

Stand Up & Paddle Cape Cod

Take the family on an outing to Stand Up & Paddle Cape Cod during your trip to Osterville. Attend a sporting event or simply enjoy the seafood restaurants while you're in the area.

Frequently asked questions

How much are vacation packages to Osterville?

Starting at just $536, flight and hotel packages are a fabulous way to stretch your vacation budget even further. Watch out Osterville — here you come!

Where can I get the best vacation package deals for Osterville?

Travelocity is the place to go to score an awesome Osterville package deal. Select from 400 partner airlines and 1,000,000 properties around the world and put together a travel itinerary that fits your style. With so many options at hand, you have inspiration galore for your next big adventure.

Why should I book my Osterville vacation package with Travelocity?

Whether you're planning a weeks-long vacation or a last-minute weekend trip, we have plenty of amazing destinations to choose from at an affordable rate. In addition, we offer round-the-clock support, superb service and a Price Match Guarantee. Save yourself money and time and lock in your dream vacation today.

Can I save on my Osterville car rental if I bundle it with my hotel or flight?

Combining your flight, car and hotel into an Osterville vacation package is a great way to score the best deal. Plus, having your own car rental gives you total freedom to find your way to all those landmarks you can't wait to see. Located 60 mi from Osterville, Fenway Park is one place that should be on your itinerary. Put together a driving playlist and make a day trip of it.

Which airport is best for Osterville?

Logan Intl. Airport (BOS) is one of the busiest airports in Osterville. It's situated 60 mi northwest of the bustling downtown area. Other options available to you are T.F. Green Airport (PVD) (55 mi away from central Osterville) and Martha's Vineyard Airport (MVY) (20 mi away from central Osterville).

What is there to do in Osterville?

Dowses Beach is one of the superb sights that make Osterville such a great place to visit. But allow some extra time to discover its lesser-known attractions too. This is often where the best vacation memories are created.

Where should I stay when visiting Osterville?

Many travelers choose to check in to the Charming 3-bedroom house in Osterville. It's an excellent base for your Osterville getaway.