Osterville Vacations from $580
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
$580
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8.6/10 Excellent! (123 reviews)
No breakfast. Very clean & quiet. Front desk very helpful. I had to ask for the ironing board and the blow dryer. Other than that, everything was perfect great location close to everything within walking distance to Main St stores.
Reviewed on Aug 26, 2026
Margaritaville Resort Cape Cod
$798
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8.6/10 Excellent! (712 reviews)
Disappointing birthday stay – major closures should be disclosed in advanceWe booked this hotel for my son’s 9th birthday specifically because he is a swimmer and loves the water; we wanted a place where he could swim all day and use the jacuzzi. Unfortunately, when we arrived, we were hit with the terrible news that the outdoor pool was closed for maintenance. This major closure should absolutely be communicated to guests prior to arrival so they can change their plans. We were promised it would re-open the next morning, but it remained closed. When we tried using the indoor jacuzzi instead, my son was kicked out because he is under 12. We deeply regret choosing this property and its Margaritaville waterpark over the Crest Hotel. We paid a premium price for amenities we couldn't use, and it was a complete waste of money.
Reviewed on Aug 31, 2026
Hyannis Plaza Hotel
$1,015
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
7.2/10 Good! (1,001 reviews)
The paint in the bathroom was chipped, and I asked for more towels when I first checked in and they were never delivered and the room had a unpleasant odor
Reviewed on Aug 31, 2026
Inn on Main
$595
per person
Nov 1 - Nov 3
found 3 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
10/10 Exceptional! (79 reviews)
Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend
Reviewed on Aug 8, 2026
Stay near popular Osterville attractions
Dowses Beach
10.0/10 (1 review)
This serene peninsula beach offers both bay and ocean waters with views across East Bay to Hyannis Port. Enjoy calm swimming, shell collecting, or fishing from the accessible wooden pier at the north end.
Public Beach
Nestled on a peninsula, Dowses Beach offers visitors both bay and ocean waters with soft sands perfect for shell collecting. Arrive early during summer to secure parking and claim your spot on this tranquil shoreline.
Stand Up & Paddle Cape Cod
Glide across Cape Cod's serene waterways with expert SUP instruction tailored to your skill level. Morning sessions offer the calmest conditions for spotting local wildlife while mastering this peaceful water sport.
Osterville Hotel Deals
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
$243 nightly
$279 total
Sep 20 - Sep 21
Total with taxes and fees
8.6/10 Excellent! (733 reviews)
"Disappointing birthday stay – major closures should be disclosed in advanceWe booked this hotel for my son’s 9th birthday specifically because he is a swimmer and loves the water; we wanted a place where he could swim all day and use the jacuzzi. Unfortunately, when we arrived, we were hit with the ..."
Reviewed on Aug 31, 2026
Bayside Resort Hotel
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$177 nightly
$202 total
Sep 20 - Sep 21
Total with taxes and fees
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
$326 nightly
$373 total
Sep 20 - Sep 21
Total with taxes and fees
7.6/10 Good! (475 reviews)
"everything was great. The beach is beautiful. The room was beautiful all the amenities and everybody was so friendly and nice. I had read some of the reviews that were a little negative, but I thought it was Fabulous"
Reviewed on Aug 31, 2026
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 $580 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.