Title: Osterville Vacation Packages 2026 from $412 | Expedia.com [Osterville Travel Guide](https://expedia.com/Osterville.dx183338)[Hotels in Osterville](https://expedia.com/Osterville-Hotels.d183338.Travel-Guide-Hotels)[Vacation Rentals in Osterville](https://expedia.com/Osterville-Vacation-Rentals.d183338.Travel-Guide-VacationRentals)[Flights to Osterville](https://expedia.com/Cheap-Flights-To-Osterville.d183338.Travel-Guide-Flights)[Car Rentals in Osterville](https://expedia.com/Car-Rentals-In-Osterville.d183338.Car-Rental-Guide) ![](https://images.trvl-media.com/place/183338/8a17e714-193f-4593-904e-60223d02c37e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Osterville Vacations from $412 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, 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](https://www.expedia.com/Cape-Codder-Water-Park-Hyannis.d553248635056398978.Vacation-Attraction), [Hyannis Harbor](https://www.expedia.com/Hyannis-Harbor-Hyannis.d6127091.Vacation-Attraction) and [Cape Cod Melody Tent](https://www.expedia.com/Cape-Cod-Melody-Tent-Hyannis.d6286857.Vacation-Attraction) 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. ![Chapter House](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196169/d1cecd38_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chapter House Save 100% on your flight $412 per person Apr 23 - Apr 27 found 9 hours ago Roundtrip flight included Chicago (CHI) 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 ![Water Access 5-bed 2-bath Retreat](https://images.trvl-media.com/lodging/116000000/115550000/115540200/115540151/44ad2736_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Water Access 5-bed 2-bath Retreat $3,428 per person Apr 23 - Apr 27 found 9 hours ago Roundtrip non-stop flight included Chicago (CHI) to Hyannis (HYA) No reviews ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Margaritaville Resort Cape Cod $1,001 per person Mar 31 - Apr 3 found 17 hours ago Roundtrip non-stop flight included Chicago (CHI) to Hyannis (HYA) 8.8/10 Excellent! (401 reviews) The report was beautiful but I think staff needs some work. At the pool bar, the bar tender didn’t seem to know the drinks and tried to over charge a few times. We went to breakfast in the morning and there was ridiculously moldy pastries in the glass, so we passed on breakfast. I’d go back for the environment but the care that was there with the Cape Coder is definitely gone. Reviewed on Feb 15, 2026 ![Anchor In Distinctive Waterfront Lodging](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/7438dff7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Anchor In Distinctive Waterfront Lodging $965 per person Mar 31 - Apr 3 found 17 hours ago Roundtrip non-stop flight included Chicago (CHI) to Hyannis (HYA) 9.4/10 Exceptional! (1,000 reviews) Location was perfect, the staff in particular at the the check in desk were beyond friendly and helpful. Would 110% recommend and stay here again. Reviewed on Feb 1, 2026 ![Hyannis Host Inn](https://images.trvl-media.com/lodging/10000000/9720000/9717400/9717349/93894fd7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyannis Host Inn $1,139 per person Apr 23 - Apr 27 found 9 hours ago Roundtrip non-stop flight included Chicago (CHI) to Hyannis (HYA) 7.8/10 Good! (457 reviews) The air conditioning was working good and the mall was on the same street so it was good Reviewed on Oct 12, 2025 Don't see what you're looking for? See all available trips from Columbus to Osterville [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-16/2026-03-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PVC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_183338) ### Discover the most popular places to visit in Osterville ![Aerial view of Dowses Beach in Osterville, MA, USA at sunset](https://images.trvl-media.com/place/553248635983994344/4a4c789c-37e9-47fb-9380-9e15f444923b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Dowses Beach Why not spend a lazy afternoon at Dowses Beach during your trip to Osterville? [](https://expedia.com/Dowses-Beach-Osterville.d553248635983994344.Vacation-Attraction) #### 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. [](https://expedia.com/Stand-Up-Paddle-Cape-Cod-Osterville.d553248621532666435.Vacation-Attraction) ## Osterville Hotel Deals ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/b57e0b1f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Margaritaville Resort Cape Cod 1225 Iyannough Rd Hyannis MA Fully refundableReserve now, pay when you stay $175 nightly $201 total Feb 17 - Feb 18 Total with taxes and fees 8.6/10 Excellent! (448 reviews) The report was beautiful but I think staff needs some work. At the pool bar, the bar tender didn’t seem to know the drinks and tried to over charge a few times. We went to breakfast in the morning and there was ridiculously moldy pastries in the glass, so we passed on breakfast. I’d go back for the ... Reviewed on Feb 15, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F17%2F2026&endDate=2%2F18%2F2026&selected=12897&PinnedHotelID=12897&HadPinnedHotel=true®ionId=183338) ![Falmouth Inn](https://images.trvl-media.com/lodging/1000000/900000/893200/893142/a26689a2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Falmouth Inn 824 Main Street Falmouth MA Fully refundableReserve now, pay when you stay $122 nightly $137 total Feb 23 - Feb 24 Total with taxes and fees 7.8/10 Good! (1,001 reviews) I stay here alot Reviewed on Jan 21, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%2F2026&selected=893142&PinnedHotelID=893142&HadPinnedHotel=true®ionId=183338) ![Iris Hotel Cape Cod ](https://images.trvl-media.com/lodging/1000000/20000/12000/11989/63513190_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Iris Hotel Cape Cod 291 Jones Rd Falmouth MA Fully refundableReserve now, pay when you stay $117 nightly $134 total Mar 14 - Mar 15 Total with taxes and fees 8.4/10 Very Good! (180 reviews) The Iris Hotel was very nicer. Check in and out was a breeze. Clean, inviting, and the service was great. The rooms were clean and tastefully decorated. The free breakfast buffet was excellent. Everything from waffles, eggs, bacon, sausage, bagels, fruit, etc. I was not expecting that. I highly recommend ... Reviewed on Feb 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F14%2F2026&endDate=3%2F15%2F2026&selected=11989&PinnedHotelID=11989&HadPinnedHotel=true®ionId=183338) [See all 6,049 properties in Osterville](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F17%2F2026&endDate=2%2F18%2F2026®ionId=183338) 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](https://www.expedia.com/Cape-Cod-Inflatable-Park-West-Yarmouth.d6286463.Vacation-Attraction), [Cape Codder Water Park](https://www.expedia.com/Cape-Codder-Water-Park-Hyannis.d553248635056398978.Vacation-Attraction) and [Mayflower Beach](https://www.expedia.com/Mayflower-Beach-Massachusetts.d553248621561930301.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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[](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does an Osterville vacation package cost? ### What are the cheapest months to go to Osterville? ### How many days is enough for Osterville? ### How to find the best Osterville package deals? ### Is it cheaper to book an Osterville vacation as a package? ### When to book a vacation package to Osterville? ### Does Expedia offer Book Now, Pay Later Osterville vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app