Osterville Vacations from $964

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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.
Courtyard Resort

Courtyard Resort

2 out of 5
Price was $1,010, price is now $964 per person
$964
per person
Dec 31 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
7.8/10 Good! (16 reviews)
Excellent location. Nicely equipped kitchenette.

Reviewed on Oct 11, 2025

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $1,341, price is now $1,124 per person
$1,124
per person
Dec 31 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
8.6/10 Excellent! (351 reviews)
Everything was good, wished our stay could have been longer.

Reviewed on Oct 9, 2025

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $1,273, price is now $1,133 per person
$1,133
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hyannis (HYA)
9.4/10 Exceptional! (1,002 reviews)
Everything was Amazing, Sandy is truly a delight, she makes this place special. Our room was amazing, beautiful waterview, and very spacious. Highly recommend.

Reviewed on Oct 11, 2025

Inn on Main

Inn on Main

3.5 out of 5
Price was $1,296, price is now $1,159 per person
$1,159
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Hyannis (HYA)
10/10 Exceptional! (71 reviews)
What a great place! Central location made it super easy to get around. Hosts were fantastic- very nice, welcoming and very helpful with great restaurant, beach or visit recommendations. I highly recommend The Inn on Main.

Reviewed on Aug 7, 2025

Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
Price was $1,070, price is now $1,003 per person
$1,003
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Hyannis (HYA)
9.6/10 Exceptional! (1,008 reviews)
Quaint accommodations. Location was amazing. Room was clean. Had everything we needed. Great price

Reviewed on Oct 11, 2025

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Discover the most popular places to visit in Osterville

Dowses Beach

Why not spend a lazy afternoon at Dowses Beach during your trip to Osterville?

Dowses Beach

Stand Up & Paddle Cape Cod

Take the family on an outing to Stand Up & Paddle Cape Cod during your trip to Osterville. Attend a sporting event or simply enjoy the seafood restaurants while you're in the area.

Stand Up & Paddle Cape Cod

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
$177 nightly
The price is $203 total per night from Oct 28 to Oct 29
$203 total
Oct 28 - Oct 29
Total with taxes and fees
8.6/10 Excellent! (374 reviews)
Fun place to stay
"Very bright and clean! Bed was very noisy and breakfast was not free but looked like a typical hotel breakfast line so that was disappointing"

Reviewed on Oct 6, 2025

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
$93 nightly
The price is $106 total per night from Nov 6 to Nov 7
$106 total
Nov 6 - Nov 7
Total with taxes and fees
8.2/10 Very Good! (117 reviews)
"Clean room, friendly staff"

Reviewed on Oct 6, 2025

Iris Hotel Cape Cod
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
$135 nightly
The price is $151 total per night from Oct 27 to Oct 28
$151 total
Oct 27 - Oct 28
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Room was tight, but it was what we choose. It was clean, water station was a great addition."

Reviewed on Oct 9, 2025

Summercamp
See all 6,027 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.

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 $964 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.