Osterville Vacations from $595

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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.
Heritage House Inn on Cape Cod, an Ascend Collection Hotel

Heritage House Inn on Cape Cod, an Ascend Collection Hotel

2.5 out of 5
Price was $675, price is now $595 per person
$595
per person
May 16 - May 19
found 6 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) to Hyannis (HYA)
8.4/10 Very Good! (20 reviews)
Great staff. Really friendly and helpful. Room was spacious and clean. Close to Main Street. I would definitely stay again the next time we visit cape cod!

Reviewed on Sep 11, 2025

Chapter House

Chapter House

3.5 out of 5
Save 100% on your flight
Price was $1,446, price is now $1,027 per person
$1,027
per person
Jul 8 - Jul 14
found 1 day ago
Roundtrip flight included
Austin (AUS) 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

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
Save 100% on your flight
Price was $2,981, price is now $2,333 per person
$2,333
per person
May 16 - May 19
found 6 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) to Hyannis (HYA)
9.4/10 Exceptional! (245 reviews)
The staff is amazing, they are kind and always looking for ways to help and make you feel welcome.

Reviewed on Jan 1, 2026

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $1,403, price is now $1,145 per person
$1,145
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip flight included
Austin (AUS) to Hyannis (HYA)
9.4/10 Exceptional! (1,000 reviews)
We were just there for 1 night. The staff was super sweet and the view was incredible!

Reviewed on Apr 8, 2026

Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod

2.5 out of 5
Price was $691, price is now $614 per person
$614
per person
May 16 - May 19
found 6 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) to Hyannis (HYA)
8/10 Very Good! (1,006 reviews)
Good location. Nice stuff. Good breakfast.

Reviewed on Apr 11, 2026

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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
$177 nightly
The price is $202 total per night from May 3 to May 4
$202 total
May 3 - May 4
Total with taxes and fees
8.6/10 Excellent! (533 reviews)
This place is “cleaner looking” since it got a Margaritaville facelift. Rugs were replaced in our room with a nice floor. Staff was friendly. Lifeguards were doing their jobs. Steel drummer in the lobby was awesome! -Waterpark and pool did not work until after we checked out. We were refunded for ...

Reviewed on Apr 15, 2026

Margaritaville Resort Cape Cod
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $138 total per night from Apr 26 to Apr 27
$138 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (1,552 reviews)
Clean room restaurant arcade great free hot buffet breakfast fire pit roasting s’mores. Fun for the family

Reviewed on Apr 13, 2026

Bayside Resort Hotel
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $132 total per night from Apr 22 to Apr 23
$132 total
Apr 22 - Apr 23
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
Clean room. Pleasant staff

Reviewed on Mar 30, 2026

Falmouth Inn
See all 6,183 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 $595 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.