Osterville Vacations from $423

Book a Hotel + Flight or Car together to unlock savings

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 $467, price is now $423 per person
$423
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
8/10 Very Good! (37 reviews)
It was ok. Best part was it was near everything.

Reviewed on Jan 18, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $640, price is now $513 per person
$513
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
8.8/10 Excellent! (401 reviews)
Excellent,very clean

Reviewed on Jan 28, 2026

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $555, price is now $468 per person
$468
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
9.4/10 Exceptional! (1,000 reviews)
Mary, at the front desk, was so extraordinarily kind- she was helpful and went out of her way to be kind. I enjoyed my stay there and felt like any question I had- or anything I needed- I could rely on Mary. She made my stay at the Anchor In- extra special

Reviewed on Jan 22, 2026

Holiday Inn Hyannis by IHG

Holiday Inn Hyannis by IHG

3 out of 5
Price was $479, price is now $446 per person
$446
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
8.2/10 Very Good! (968 reviews)
Herman was fantastic checking us in!

Reviewed on Jan 3, 2026

Courtyard By Marriott Cape Cod Hyannis

Courtyard By Marriott Cape Cod Hyannis

3 out of 5
Price was $545, price is now $508 per person
$508
per person
Mar 23 - Mar 27
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Hyannis (HYA)
8.8/10 Excellent! (483 reviews)
Parking was free and easy, room was very clean and housekeeping service was top notch.

Reviewed on Dec 22, 2025

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Discover the most popular places to visit in Osterville

Aerial view of Dowses Beach in Osterville, MA, USA at sunset

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
$184 nightly
The price is $211 total per night from Feb 23 to Feb 24
$211 total
Feb 23 - Feb 24
Total with taxes and fees
8.6/10 Excellent! (437 reviews)
Excellent,very clean

Reviewed on Jan 28, 2026

Margaritaville Resort Cape Cod
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $136 total per night from Feb 11 to Feb 12
$136 total
Feb 11 - Feb 12
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
I stay here alot

Reviewed on Jan 21, 2026

Falmouth Inn
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Feb 5 to Feb 6
$118 total
Feb 5 - Feb 6
Total with taxes and fees
8.6/10 Excellent! (1,545 reviews)
Very helpful staff, they had a map ready for us to out room, all of our perks ready as well. Very clean and quiet. Felt very safe.

Reviewed on Jan 25, 2026

Bayside Resort Hotel
See all 6,049 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.

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 $423 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.