Osterville Vacations from $323
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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.
Anchor In Distinctive Waterfront Lodging
Save 100% on your flight
Price was $541, price is now $341 per person
$341
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hyannis (HYA)
9.4/10 Exceptional! (1,000 reviews)
Nice people, clan room, nice view
Reviewed on Nov 23, 2025
Margaritaville Resort Cape Cod
Save 100% on your flight
Price was $817, price is now $570 per person
$570
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hyannis (HYA)
8.8/10 Excellent! (401 reviews)
The rooms were clean and spacious. The majority of the staff was nice and welcoming. The waterpark was a lot of fun, and the land shark is reasonably priced. However there are a few things that could be improved. There was some staff that just seemed irritated everytime I asked a question (which wasn’t often). The water was freezing even though it’s advertised as heated. My 4yr old couldn’t even get into the kiddy area because that was like ice water. They don’t explain where anything is so you’ll spend a good portion of your time walking around trying to find where everything is and no one seems to want to help. My daughter got sick and we needed new sheets (I would have put them on myself) and they were taking their sweet time to get around to us so we ended up walking till we found someone to come with new sheets. There are no microwaves in the rooms so you have to go to the front desk. However the lady that was working the front had to do triple duty and we felt terrible for her. It was also irritating that I had to go back everyday for our water passes. The land shark restaurant was ok food, to much sea food for people like me who are allergic. Also the staff got irritated with me when I asked for cheese for my tacos. They were to plain for me as I’m Mexican.
Reviewed on Nov 17, 2025
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?
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.
Osterville Hotel Deals
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
867 Iyannough Road Hyannis MA
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $122 total per night from Dec 7 to Dec 8
$122 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (646 reviews)
Yes good breakfast kept filled. Friendly staff. Good AC heat system
Reviewed on Nov 20, 2025
Cape Sands Inn
149 Main St - RT 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Nov 27 to Nov 28
$85 total
Nov 27 - Nov 28
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
With the exception of the sticky bathroom floor the room was spotless. In the small floor area my socks and shoes stuck to the floor until I purposely lifted the leg. Rest of bathroom spotless. Plenty of linens, hand soap and tissues. Quiet even on Main St with lots of traffic. Plenty of rooms all ...
Reviewed on Nov 23, 2025
Falmouth Inn
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $148 total per night from Dec 3 to Dec 4
$148 total
Dec 3 - Dec 4
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
Clean room. Nice staff, convenient location. We enjoyed a drink and live music at the restaurant attached.
Reviewed on Nov 16, 2025
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.