Osterville Vacation Packages 2025/2026 from $794

Osterville flight + hotel vacation packages

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

Inn on Main

$794

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) 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.

Chapter House

$1,193

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip flight included

New York (NYC) to Hyannis (HYA)

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

Margaritaville Resort Cape Cod

$1,175

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

New York (NYC) 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.

Anchor In Distinctive Waterfront Lodging

$1,391

per person

Oct 17 - Oct 21

found 1 day ago

Roundtrip flight included

Indianapolis (IND) 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.

Courtyard Resort

$1,084

per person

Nov 27 - Dec 2

found 1 day ago

Roundtrip flight included

New York (NYC) 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 and a computer station are also offered on site.

Top Osterville hotels deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$221 total

Sep 21 - Sep 22

Total with taxes and fees

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.

Pool

Hot Tub

Bayside Resort Hotel

225 Route 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$176 total

Sep 21 - Sep 22

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.

Pool

Hot Tub

Sea Crest Beach Resort

350 Quaker Rd, North Falmouth, MA

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$215 total

Sep 21 - Sep 22

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.

On private beach

Pool

Falmouth Inn

824 Main Street, Route 28, Falmouth, MA

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$157 total

Sep 15 - Sep 16

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.

Pool

Breakfast included

Cape Sands Inn

149 Main St - RT 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$90 total

Sep 14 - Sep 15

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

Hyannis Plaza Hotel

662 Main Street, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$112 total

Oct 6 - Oct 7

Total with taxes and fees

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.

Pool

Parking included

Don't see what you're looking for?

See all available properties in Osterville

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.

Frequently asked questions

How much are vacation packages to Osterville?

Starting at just $794, 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.