Osterville Vacations from $958
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Osterville Vacation
Come and experience this captivating city for yourself with a Osterville vacation package. Consider staying in the neighborhood of Mashpee Neck, which is great for walking and views, and your time here will be nothing short of unforgettable. Ready to start exploring your surroundings? Cape Codder Water Park, Hyannis Harbor and Cape Cod Melody Tent are three of the best places to visit during your trip to Osterville. Whoever you're heading away with and whatever you want to spend, your ultimate Osterville vacation is only clicks away with Expedia.
The Latest Osterville vacation packages
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod
$1,391
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Hyannis (HYA)
8.6/10 Excellent! (784 reviews)
We stayed here for a wedding we had off property. Had a fun time. I would stay here again. Water park was clean and many lifeguards on duty.
Reviewed on Oct 18, 2026
Courtyard Resort
$1,460
per person
Dec 3 - Dec 7
found 16 hours ago
Roundtrip flight included
Appleton (ATW) to Hyannis (HYA)
8.6/10 Excellent! (143 reviews)
Enjoyed my stay, except walls very thin and even the rain was super loud. Stay on 1st or 2nd floor, away from the main road. Terrific staff. Nice spacious room with great amenities.
Reviewed on Oct 12, 2026
Stay near popular Osterville attractions
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.
Public Beach
Nestled on a peninsula, Dowses Beach offers visitors both bay and ocean waters with soft sands perfect for shell collecting. Arrive early during summer to secure parking and claim your spot on this tranquil shoreline.
Stand Up & Paddle Cape Cod
Glide across Cape Cod's serene waterways with expert SUP instruction tailored to your skill level. Morning sessions offer the calmest conditions for spotting local wildlife while mastering this peaceful water sport.
Osterville Hotel Deals
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
$169 nightly
$193 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (536 reviews)
"Full ocean view rooms desperately need updating. Staff was not super helpful in trying to switch rooms."
Reviewed on Oct 18, 2026
Inn on the Square
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
$142 nightly
$163 total
Oct 28 - Oct 29
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"The hotel was clean, with great staff. Perfect location to walk to downtown to shops, restaurants and bars. Went for marathon. Easy walk to everything"
Reviewed on Oct 18, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
$120 nightly
$137 total
Nov 19 - Nov 20
Total with taxes and fees
8.4/10 Very Good! (430 reviews)
"Good breakfast"
Reviewed on Oct 18, 2026
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.
Find the Best Osterville Vacation Packages
Osterville Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Nantucket Memorial Airport (ACK) |
Population | 2,900 |
Max Temp Winter | 40ºF |
Max Temp Summer | 70ºF |
Top Sights | Cape Cod Inflatable Park, Cape Codder Water Park and Mayflower Beach |
More vacations you might like
Frequently asked questions
How much does an Osterville vacation package cost?
Offering great value package deals from $958 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
