Osterville Vacation Packages 2026 from $929

Osterville flight + hotel vacation packages

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

Inn on Main

$929

per person

Dec 6 - Dec 10

found 13 hours ago

Roundtrip flight included

Atlanta (ATL) to Hyannis (HYA)

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free cooked-to-order breakfast each morning. A garden, a snack bar/deli, and a library are also on offer.

Hyannis Plaza Hotel

$1,188

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Margaritaville Resort Cape Cod

$1,211

per person

Nov 5 - Nov 9

found 5 hours ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) 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.

Courtyard Resort

$1,017

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Hyannis (HYA)

This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a garden, and a picnic area are also offered.

Courtyard By Marriott Cape Cod Hyannis

$1,153

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Hyannis (HYA)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a coffee shop, and a terrace are also offered.

Top Osterville hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$228 total

per night

Oct 4 - Oct 5

Pool

Hot Tub

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

Free Cancellation

Reserve now, pay when you stay

$264 total

per night

Oct 12 - Oct 13

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.

On private beach

Pool

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA

Free Cancellation

Reserve now, pay when you stay

$152 total

per night

Oct 12 - Oct 13

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.

Pool

Pet friendly

Bayside Resort Hotel

225 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$192 total

per night

Oct 12 - Oct 13

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.

Pool

Hot Tub

Uncommoner Hotel by Reverie Boutique Collection

135 Route 28 West Yarmouth MA

Free Cancellation

Reserve now, pay when you stay

$156 total

per night

Oct 13 - Oct 14

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.

Pool

Parking included

Lighthouse Inn

1 Lighthouse Inn Rd West Dennis MA

$171 total

per night

Sep 27 - Sep 28

A private beach and an outdoor tennis court are featured at this smoke-free hotel. Spend a day at the beach windsurfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with mini golf and a playground, and families will appreciate the onsite laundry facilities.

On private beach

Pool

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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 $929, 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.