Osterville Vacations from $295

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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 Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
Price was $328, price is now $295 per person
$295
per person
Mar 15 - Mar 18
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
7/10 Good! (956 reviews)
The best staff abd it was clean and beautiful

Reviewed on Dec 31, 2025

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $414, price is now $322 per person
$322
per person
Mar 15 - Mar 18
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
9.4/10 Exceptional! (1,000 reviews)
The Anchor In is a lovely hotel with friendly staff and clean, updated rooms. It is very convenient to the ferry and to various dining options in Hyannis. Great place to stay!

Reviewed on Jan 11, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $477, price is now $376 per person
$376
per person
Mar 15 - Mar 18
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8.8/10 Excellent! (401 reviews)
Evrything is so clean! We love staying here with our family with small children. The kids love it and so do we! We go back every year. It's become a tradition!

Reviewed on Jan 10, 2026

Courtyard Resort

Courtyard Resort

2 out of 5
Price was $348, price is now $310 per person
$310
per person
Mar 15 - Mar 18
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8/10 Very Good! (37 reviews)
It was ok. Best part was it was near everything.

Reviewed on Jan 18, 2026

Courtyard By Marriott Cape Cod Hyannis

Courtyard By Marriott Cape Cod Hyannis

3 out of 5
Price was $409, price is now $372 per person
$372
per person
Mar 15 - Mar 18
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) 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

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

Dowses Beach

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

Dowses Beach

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
$181 nightly
The price is $207 total per night from Feb 2 to Feb 3
$207 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (428 reviews)
Evrything is so clean! We love staying here with our family with small children. The kids love it and so do we! We go back every year. It's become a tradition!

Reviewed on Jan 10, 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
$122 nightly
The price is $137 total per night from Jan 26 to Jan 27
$137 total
Jan 26 - Jan 27
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
Room was clean. Staff was friendly

Reviewed on Jan 4, 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
$105 nightly
The price is $120 total per night from Feb 5 to Feb 6
$120 total
Feb 5 - Feb 6
Total with taxes and fees
8.6/10 Excellent! (1,537 reviews)
The place was clean, staff very nice and a good breakfast! Nice pool and beach area.

Reviewed on Jan 16, 2026

Bayside Resort Hotel
See all 6,052 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 $295 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.