Osterville Vacation Packages 2026 from $810

Osterville flight + hotel vacation packages

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

Inn on Main

$810

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Hyannis (HYA)

This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. 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 garden, a snack bar/deli, and a library are also on offer.

Anchor In Distinctive Waterfront Lodging

$933

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Hyannis (HYA)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a snack bar/deli are also on offer.

Wequassett Resort and Golf Club

$1,586

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Hyannis (HYA)

A private beach, 6 restaurants, and 4 outdoor tennis courts are all featured at this luxury resort. Enjoy a day at the beach kayaking, or relax with beach umbrellas. There's fun for all ages with a children's club and a playground, and babysitting is an added bonus.

Margaritaville Resort Cape Cod

$813

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.

Chapter House

$888

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Hyannis (HYA)

A bar/lounge and a terrace are featured at this guesthouse, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.

Top Osterville hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$272 nightly

$312 total

Aug 19 - Aug 20

Total with taxes and fees

Pool

Hot Tub

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA

$220 nightly

$252 total

Aug 18 - Aug 19

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.

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

$493 nightly

$564 total

Aug 2 - Aug 3

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.

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA

$296 nightly

$337 total

Jul 23 - Jul 24

Total with taxes and fees

The hotel's indoor pool, seasonal outdoor pool, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free self parking and free WiFi. A coffee shop, a garden, and a picnic area are also on offer.

Cape Sands Inn

149 Main St - RT 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$170 total

Jul 23 - Jul 24

Total with taxes and fees

This motel features an indoor pool and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the hot tub and perks like free self parking and free WiFi.

Pool

Hot Tub

Falmouth Inn

824 Main Street Falmouth MA

Free Cancellation

Reserve now, pay when you stay

$158 nightly

$178 total

Aug 5 - Aug 6

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.

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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.

Stay near popular Osterville attractions

A wooden pier with a sunset view over the water.

Dowses Beach

10.0/10 (1 review)

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

See properties

Frequently asked questions

How much are vacation packages to Osterville?

Starting at just $810, 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.