Osterville Vacations from $335

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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 $400, price is now $335 per person
$335
per person
Oct 30 - Nov 2
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8/10 Very Good! (9 reviews)
Staff super friendly, helpful!!!

Reviewed on Aug 20, 2025

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Save 100% on your flight
Price was $544, price is now $374 per person
$374
per person
Oct 30 - Nov 2
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8.8/10 Excellent! (278 reviews)
Very family friendly, great pool, multiple fire pit for roasting marshmallows, indoor heated water park, arcade games. There is a cafe, a gift shop, a bar and restaurant with a door and out in the center of the resort where there is fire piths, a ballroom inside for free dance lessons. There is free live music multiple times per day, and much more activities to keep families with young kids entertained. There is a text through out the day alerting for the activities. If you don’t have a car and want to go anywhere, the resort offers shuttle services to drop you off anywhere in town and pick you up.

Reviewed on Aug 23, 2025

Chapter House

Chapter House

3.5 out of 5
Save 100% on your flight
Price was $737, price is now $510 per person
$510
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
9.2/10 Wonderful! (156 reviews)
Really enjoyed the bar, which was a great spot for a late afternoon drink before dinner

Reviewed on Aug 2, 2025

Inn on Main

Inn on Main

3.5 out of 5
Save 100% on your flight
Price was $1,104, price is now $786 per person
$786
per person
Oct 6 - Oct 10
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
10/10 Exceptional! (70 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

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $583, price is now $441 per person
$441
per person
Oct 30 - Nov 2
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
9.4/10 Exceptional! (1,003 reviews)
The hotel is very well managed nicely maintained. Great harbour location for catching the ferries as well. The breakfast is prepackaged items designed for grab and go.

Reviewed on Aug 19, 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
$201 nightly
The price is $230 total per night from Sep 14 to Sep 15
$230 total
Sep 14 - Sep 15
Total with taxes and fees
8.6/10 Excellent! (294 reviews)
"Na"

Reviewed on Aug 24, 2025

Margaritaville Resort Cape Cod
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $170 total per night from Sep 1 to Sep 2
$170 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,009 reviews)
"The property was quiet. The beds were extremely comfortable and we slept very well both nights. The morning breakfast was great with lots of variety."

Reviewed on Aug 25, 2025

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
$186 nightly
The price is $213 total per night from Sep 25 to Sep 26
$213 total
Sep 25 - Sep 26
Total with taxes and fees
8.6/10 Excellent! (1,487 reviews)
"Older hotel with good location."

Reviewed on Aug 24, 2025

Bayside Resort Hotel
See all 6,351 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.

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Frequently asked questions

How much does an Osterville vacation package cost?
Offering great value package deals from $335 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.