Osterville Vacations from $449
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The Latest Osterville Vacation Packages
- Courtyard Resort
Aug 25 - Aug 28Courtyard Resort + Flight
Hyannis3 nights2.0 star property8.6/10 - Excellent (100 reviews)"Studio was exceptionally clean.Loved it!"Reviewed July 9, 2026Roundtrip • Chicago (CHI) - Hyannis (HYA)ORD - MVY • 1 stop MVY - ORD • 1 stop$521$449found 1 day agoper traveler - Anchor In Distinctive Waterfront Lodging
Sep 4 - Sep 7Anchor In Distinctive Waterfront Lodging + Flight
Hyannis3 nights3.0 star property9.4/10 - Exceptional (1,000 reviews)"This is a beautiful property situated right on the hyannis pier. It was really cool to see the ferries and ships enter/depart from the harbor. Continental breakfast was wonderful and plentiful. Pool area was very clean. Rocky gave us some great tips on how to obtain some fishing gear. He always had a smile on his face and you can tell he enjoys what he does. We would definitely stay here again."Reviewed July 16, 2026Roundtrip • New York (EWR) - Hyannis (HYA)EWR - BOS • Nonstop BOS - EWR • Nonstop - Wequassett Resort and Golf Club
Aug 20 - Aug 23Wequassett Resort and Golf Club + Flight
Harwich3 nights5.0 star property9.4/10 - Exceptional (262 reviews)"Everything is nice Bed was not comfortable Not a great value, but nice place"Reviewed July 1, 2026Roundtrip • Chicago (CHI) - Hyannis (HYA)ORD - BOS • Nonstop BOS - ORD • 1 stop - Inn on Main
Aug 27 - Aug 30Inn on Main + Flight
Yarmouth Port3 nights3.5 star property10/10 - Exceptional (75 reviews)"I cannot recommend this property enough. David and Ruta are amazing hosts. They are so considerate and helpful. Breakfast is wonderful and they are more than willing to accommodate any dietary needs. The property is beautiful and well maintained. They have drawers full of travel supplies, and there are fresh baked cookies every day, in your room! The Inn is very well situated and walkable to some good restaurants (plan ahead to have dinner at the Old Yarmouth Inn). The Inn on Main is really not..."Reviewed June 22, 2026Roundtrip • Chicago (CHI) - Hyannis (HYA)ORD - BOS • 1 stop BOS - ORD • 1 stop$1,024$877found 1 day agoper traveler - Chapter House
Sep 18 - Sep 21Chapter House + Flight
Yarmouth Port3 nights3.5 star property9.2/10 - Wonderful (176 reviews)"Lovely property in a quiet area of Cape Cod. A few shops within walking distance and a twenty minute drive from the shops of Chatham. Nice grounds. The floor of the room was a bit grimy."Reviewed July 11, 2026Roundtrip • Chicago (CHI) - Hyannis (HYA)ORD - BOS • 1 stop BOS - ORD • 1 stop$835$723found 23 hours agoper traveler
Discover the most popular places to visit in Osterville
Osterville Hotel Deals
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
Frequently Asked Questions
How much does an Osterville vacation package cost?
Offering great value package deals from $449 on Expedia, you'll be thrilled with how little a vacation to Osterville costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Osterville?
If you'd like to book a cheap Osterville vacation package, consider traveling in November, December and January. You'll typically find better prices on airfares and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Osterville?
The ideal length for your Osterville vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you time to check out all the major attractions and explore some hidden treasures along the way.
How to find the best Osterville package deals?
Begin your search for an Osterville package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Osterville package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Osterville adventure underway.
Is it cheaper to book an Osterville vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Osterville vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Osterville?
If you're considering a spontaneous Osterville vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Osterville vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Osterville break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.