Osterville Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

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

  • 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 SARĀ 963 per night from Aug 6 to Aug 7
SARĀ 963
SARĀ 1,317 total
6 Aug - 7 Aug
includes taxes & fees
8.6/10 Excellent! (628 reviews)
"Well, overall, a lovely experience. Our first night with room facing Waterpark was not my favorite part. Just wasnt the best for us that need fresh air coming in so the next night we were moved to courtyard view with patio to sit out and enjoy the beautiful evening. Loved the area for the lawn games, ..."

Reviewed on 17 July 2026

Margaritaville Resort Cape Cod
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 SARĀ 826 per night from Aug 17 to Aug 18
SARĀ 826
SARĀ 946 total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (290 reviews)
"Beautiful room, very clean and well kept property. Breakfast was outstanding. Staff was very accommodating and helpful. I would highly recommend this Iris Inn!"

Reviewed on 15 July 2026

Iris Hotel Cape Cod
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
The price is SARĀ 1,673 per night from Aug 2 to Aug 3
SARĀ 1,673
SARĀ 2,130 total
2 Aug - 3 Aug
includes taxes & fees
Sea Crest Beach Resort
See all 6,426 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.

Stay near popular Osterville attractions

A wooden pier with a sunset view over the water.

Dowses Beach

10.0/10 (1 review)
This serene peninsula beach offers both bay and ocean waters with views across East Bay to Hyannis Port. Enjoy calm swimming, shell collecting, or fishing from the accessible wooden pier at the north end.
See properties

Frequently asked questions

How much does an Osterville vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Osterville costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Osterville?
To pick up cheap Osterville vacation packages, plan your getaway outside of peak times like public holidays and major events. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How to find the best Osterville package deals?
Use Expedia's filters to find some terrific Osterville package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Osterville package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
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 usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Osterville vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Osterville?
If you've got your Osterville vacation dates locked in, book as early as you can to score some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Osterville?

  1. Choose your travel dates: What you plan to do in Osterville and your preferred season can help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Osterville.
  3. Decide how long to go for: Now that you know more about Osterville, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the right Osterville vacation package for you.