Osterville Vacations

Book a Hotel + Flight or Car together to unlock savings

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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

Riviera Beach Resort
Riviera Beach Resort
3 out of 5
327 South Shore Drive, South Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is ₩548,125 per night from Jul 6 to Jul 7
₩548,125
₩696,335 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very Good! (1,007 reviews)
"Loved being right on the beach and having a pool right outside the rooms. Would’ve given 5 stars if they had more food options on site. They used to have a grill at the beach bar but no longer have that, only overpriced grab and go sandwich options. Also be aware that they automatically charge a ..."

Reviewed on Jul 1, 2025

Riviera Beach Resort
Iris Hotel Cape Cod
Iris Hotel Cape Cod
3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is ₩297,054 per night from Jul 7 to Jul 8
₩297,054
₩339,978 total
Jul 7 - Jul 8
includes taxes & fees
7.8/10 Good! (35 reviews)
The Best Hotel in Falmouth
"I had such a wonderful stay at the Iris Hotel Cape Cod! The location is truly ideal: just a short drive from the beach and the ferry, and only minutes away from downtown Falmouth. There are plenty of great dining options nearby within walking distance, including a cozy local favorite, Jack’s Restaurant. ..."

Reviewed on Jun 27, 2025

Iris Hotel Cape Cod
Cape Sands Inn
Cape Sands Inn
2.5 out of 5
149 Main St - RT 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is ₩183,929 per night from Jul 9 to Jul 10
₩183,929
₩210,515 total
Jul 9 - Jul 10
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
Amazing manager
"The manager Lenny was amazing. Our tub was broke and we could not use it. Lenny gave us our nights free for the incovenience... and he was so nice about it all."

Reviewed on Jun 29, 2025

Cape Sands Inn
See all 6,437 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.