Osterville Vacations from $1,655
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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.
Doubletree by Hilton Cape Cod - Hyannis
$1,700
per person
Dec 2 - Dec 5
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Hyannis (HYA)
8.4/10 Very Good! (948 reviews)
Unfortunately, our room had a strong musty smell. You could smell it as you approached the area of the building. We were only there for one night, so decided to grin and bear it.
Reviewed on Oct 13, 2026
Inn on Main
$1,688
per person
Dec 3 - Dec 5
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Hyannis (HYA)
10/10 Exceptional! (80 reviews)
Ruta and David were excellent hosts. The Inn is lovely and has a beautiful yard with outdoor seating. The rooms were very clean, spacious and well appointed. The breakfasts were outstanding. The Inn is in a great location for exploring the Cape. I would highly recommend a visit to the Inn on Main.
Reviewed on Sep 27, 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
Inn on the Square
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
$142 nightly
$163 total
Nov 12 - Nov 13
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"Very helpful & friendly staff. Walkable to stores & Restaurants."
Reviewed on Oct 14, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
$162 nightly
$186 total
Nov 1 - Nov 2
Total with taxes and fees
7.6/10 Good! (534 reviews)
"Beautiful location! Our stay was just overnight so didn’t get to enjoy it to its fullest."
Reviewed on Oct 16, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
$129 nightly
$148 total
Nov 15 - Nov 16
Total with taxes and fees
8.4/10 Very Good! (428 reviews)
"Great pet friendly hotel. Continental breakfast very good. Staff very friendly and helpful. Room very clean but bath tub needs updating( non skid strips with ground in dirt, which looks like from many years of use). Loved the Iris colored decor, even the lighting outside is purple!Could use more ..."
Reviewed on Oct 16, 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 |
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Frequently asked questions
How much does an Osterville vacation package cost?
Offering great value package deals from $1,655 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.
