Osterville Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Osterville Vacation Packages

Osterville Hotel Deals

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is ₩211,573 per night from Sep 14 to Sep 15
₩211,573
₩322,227 total
Sep 14 - Sep 15
includes taxes & fees
8.6/10 Excellent! (286 reviews)
"Extremely nice beds. The whole place was clean. Very well decorated."

Reviewed on Aug 22, 2025

Margaritaville Resort Cape Cod
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is ₩208,494 per night from Sep 1 to Sep 2
₩208,494
₩259,610 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"The hotel is convoy to down town, clean and seemed updated since last visit. The price was right."

Reviewed on Aug 21, 2025

Falmouth Inn
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is ₩251,872 per night from Sep 1 to Sep 2
₩251,872
₩304,290 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,491 reviews)
Good hotel
"Stay was great, we love the bayside!"

Reviewed on Aug 21, 2025

Bayside Resort Hotel
See all 6,351 properties in Osterville
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 does an Osterville vacation package cost?
Offering great value package deals 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?
The off-season is the best time to visit Osterville if you're trying to keep costs down. Another tip for finding cheap Osterville vacation packages? Try to avoid public holidays and any major festivals or events.
How many days is enough for Osterville?
The ideal duration for your Osterville vacation depends on what you'd like to do. Usually, a handful of days to a week will give you time to visit all the main 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.
How to plan a trip to Osterville?

  1. Pick the ideal time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Osterville.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodations will likely be the largest expense during your trip to Osterville.
  3. Decide how long to go away for: Now that you know more about Osterville, you can figure out the ideal length of your break. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to choose an Osterville vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.