Osterville Vacations from $385

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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

Hyannis Host Inn

2 out of 5
Price was $420, price is now $385 per person
$385
per person
Apr 9 - Apr 12
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hyannis (HYA)
7.8/10 Good! (457 reviews)
The air conditioning was working good and the mall was on the same street so it was good

Reviewed on Oct 12, 2025

Chapter House

Chapter House

3.5 out of 5
Price was $681, price is now $547 per person
$547
per person
Apr 9 - Apr 12
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hyannis (HYA)
9.2/10 Wonderful! (162 reviews)
This property was clean and well maintained. There was ample parking and the staff was very friendly.

Reviewed on Sep 26, 2025

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $743, price is now $600 per person
$600
per person
Apr 9 - Apr 12
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hyannis (HYA)
8.8/10 Excellent! (401 reviews)
The room was great. Comfy, clean, and colorful. I enjoyed my spa treatments and use of the hot tub. I had fun and good food at the Sharks Fin Bar. I did not understand why I was charged a resort fee. Many of the extras were available to anyone who walked through the doors.

Reviewed on Jan 24, 2026

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $545, price is now $454 per person
$454
per person
Apr 9 - Apr 12
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) 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

Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
Price was $444, price is now $411 per person
$411
per person
Apr 9 - Apr 12
found 22 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Hyannis (HYA)
9.6/10 Exceptional! (1,004 reviews)
Very kind staff. Functional, clean room. Had an early bus and they let me take a few things for breakfast the night before.

Reviewed on Dec 7, 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
$181 nightly
The price is $207 total per night from Feb 9 to Feb 10
$207 total
Feb 9 - Feb 10
Total with taxes and fees
8.6/10 Excellent! (433 reviews)
Clean room Most of the staff friendly Some staff indifferent

Reviewed on Jan 21, 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 Feb 2 to Feb 3
$137 total
Feb 2 - Feb 3
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
I stay here alot

Reviewed on Jan 21, 2026

Falmouth Inn
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
23 Kelly Street Edgartown MA
8.8/10 Excellent! (999 reviews)
Very cozy comfortable hotel!!

Reviewed on Dec 17, 2025

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Faraway Martha's Vineyard
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.

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 $385 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.