Osterville Vacations from $370

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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.
Hyannis Host Inn
Anchor In Distinctive Waterfront Lodging
Chapter House
Inn on Main
Margaritaville Resort Cape Cod
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Discover the most popular places to visit in Osterville

Osterville Hotel Deals

Iris Hotel Cape Cod
Iris Hotel Cape Cod
3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $251 total per night from Jul 20 to Jul 21
$251 total
Jul 20 - Jul 21
Total includes taxes and fees
8/10 Very Good! (38 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
$129 nightly
The price is $147 total per night from Jul 13 to Jul 14
$147 total
Jul 13 - Jul 14
Total includes taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Problem with finding a parking spot upon return from. Not certain why there was not a spot for every room. Had to park in a spot marked for compact cars only parking spot. Went out at 5 am to move car to available open spot."

Reviewed on Jul 8, 2025

Cape Sands Inn
Bayside Resort Hotel
Bayside Resort Hotel
3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
$248 nightly
The price is $284 total per night from Jul 10 to Jul 11
$284 total
Jul 10 - Jul 11
Total includes taxes and fees
8.8/10 Excellent! (1,382 reviews)
"Clean room. Nice staff. Well kept grounds. Great breakfast and pool area. Hallways and rooms were a bit musty and dark. Pub did not serve food as on the website and complementary drinks couldn’t be purchased at the pool. Only at the pub which didn’t open til 5 pm. Sandwich at pool was AWFUL!"

Reviewed on Jul 7, 2025

Bayside Resort Hotel
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 $370 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.