Deals on vacations and trips to Osterville

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Osterville flight + hotel vacation packages

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

Chapter House

3.5 out of 5
Save 100% on your flight
per person
Jul 14 - Jul 18
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
per person
Aug 12 - Aug 17
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Inn on Main

Inn on Main

3.5 out of 5
per person
Aug 14 - Aug 17
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.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
per person
Aug 12 - Aug 17
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
A water park, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. 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 gym and perks like free self parking and free WiFi.
Hyannis Host Inn

Hyannis Host Inn

2 out of 5
per person
Aug 12 - Aug 17
found 18 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Concierge services are provided for your convenience.

Top Osterville hotels deals

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd, North Falmouth, MA
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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
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
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This hotel features free WiFi in public areas, concierge services, and self parking. A snack bar/deli and luggage storage are also provided.
Free WiFi
Air conditioning
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

2.5 out of 5
867 Iyannough Road, Hyannis, MA
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Pool
Breakfast included
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
18 North St, Hyannis, MA
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This hotel features an outdoor pool and an indoor pool. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and express check-out are also on offer.
Pool
Hot Tub
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Free Cancellation
Reserve now, pay when you stay
Get rates
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
Inn on the Square

Inn on the Square

3.5 out of 5
40 North Main Street, Falmouth, MA
Free Cancellation
Reserve now, pay when you stay
Get rates
A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. A garden and a safe deposit box are also provided.
Pool
Free WiFi
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See all available properties in Osterville
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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?

Dowses Beach

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.

Stand Up & Paddle Cape Cod

Public Beach

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

Public Beach

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.

Photos of local treasures

Browse Osterville vacation photos for more inspiration

Osterville featuring a bay or harbor and a coastal town
Osterville featuring signage
Osterville featuring signage
Osterville featuring a bay or harbor
Osterville showing signage