Osterville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Osterville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Courtyard Resort
CA $793
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
Hyannis Plaza Hotel
CA $814
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
Margaritaville Resort Cape Cod
CA $1,019
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
Ready to book your vacation to Osterville?
Osterville Hotel Deals
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
CA $266
CA $384 total
Sep 20 - Sep 21
includes taxes & 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
CA $224
CA $272 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,584 reviews)
"We had a wonderful overnight stay. The room was very clean and the staff was very helpful. Will definitely stay here again."
Reviewed on Aug 31, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
CA $384
CA $519 total
Sep 20 - Sep 21
includes taxes & 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.
Stay near popular Osterville attractions
Dowses Beach
10.0/10 (1 review)
Why not spend a lazy afternoon at Dowses Beach during your trip to Osterville?
Public Beach
Why not spend a lazy afternoon at Public Beach during your trip to 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.
Frequently asked questions
How much does an Osterville vacation package cost?
Offering great value package deals from CA $793 on Expedia, you'll be pleasantly surprised at how much a vacation to Osterville costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Osterville?
To pick up cheap Osterville vacation packages, plan your getaway outside of peak times like public holidays and major events. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Osterville?
To get the most out of your Osterville vacation, we recommend staying for 4 days. Divide your time between visiting Kalmus Beach, Popponesset Beach and other major sights, in addition to exploring neighbourhoods like Sandalwood Village and West Hyannisport. If you've got some time to spare, add a day trip or tour to your Osterville vacation itinerary.
How to find the best Osterville package deals?
Use Expedia's filters to find some terrific Osterville package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Osterville package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
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 usually get a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Osterville vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Osterville?
If you've got your Osterville vacation dates locked in, book as early as you can to score some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Osterville?
- Choose your travel dates: What you plan to do in Osterville and your preferred season can help you decide when to go.
- Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Osterville.
- Decide how long to go for: Now that you know more about Osterville, you can work out the perfect length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
- Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the right Osterville vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
