Title: Osterville Vacation Packages 2026 from $387 | 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 $387 ## 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. ![Hyannis Host Inn](https://images.trvl-media.com/lodging/10000000/9720000/9717400/9717349/56fb3cfe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyannis Host Inn $387 per person May 22 - May 25 found 1 day ago Roundtrip 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 ![Margaritaville Resort Cape Cod](https://images.trvl-media.com/lodging/1000000/20000/12900/12897/30f6a06a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Margaritaville Resort Cape Cod Save 100% on your flight $761 per person May 22 - May 25 found 1 day ago Roundtrip flight included Chicago (CHI) to Hyannis (HYA) 8.6/10 Excellent! (473 reviews) No amenities included.Housekeeping knocked on our door at 9am even though we had a do not disturb on the door.The hotel and check in staff was awesome Reviewed on Mar 8, 2026 ![Anchor In Distinctive Waterfront Lodging](https://images.trvl-media.com/lodging/8000000/7650000/7640900/7640889/87d9418f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Anchor In Distinctive Waterfront Lodging $748 per person May 22 - May 25 found 1 day ago Roundtrip flight included Chicago (CHI) to Hyannis (HYA) 9.4/10 Exceptional! (1,002 reviews) Marry was great Room outdated and small Reviewed on Mar 7, 2026 ![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 $3,552 per person May 29 - Jun 2 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Hyannis (HYA) No reviews ![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 $1,342 per person May 29 - Jun 2 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) 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 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/2026-04-09/2026-04-16/?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/1000000/20000/12900/12897/30f6a06a_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 Mar 16 - Mar 17 Total with taxes and fees 8.6/10 Excellent! (477 reviews) No amenities included.Housekeeping knocked on our door at 9am even though we had a do not disturb on the door.The hotel and check in staff was awesome Reviewed on Mar 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=12897&PinnedHotelID=12897&HadPinnedHotel=true®ionId=183338) ![Bayside Resort Hotel](https://images.trvl-media.com/lodging/1000000/900000/896700/896697/783b5af0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bayside Resort Hotel 225 Route 28 West Yarmouth MA Fully refundableReserve now, pay when you stay $104 nightly $118 total Mar 12 - Mar 13 Total with taxes and fees 8.8/10 Excellent! (1,552 reviews) Staff was very helpful! Reviewed on Mar 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=896697&PinnedHotelID=896697&HadPinnedHotel=true®ionId=183338) ![Aiden by Best Western Cape Cod - West Yarmouth](https://images.trvl-media.com/lodging/39000000/38360000/38357900/38357891/03e2a40a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Aiden by Best Western Cape Cod - West Yarmouth 476 Route 28 West Yarmouth MA Fully refundableReserve now, pay when you stay $91 nightly $104 total Mar 10 - Mar 11 Total with taxes and fees 8/10 Very Good! (1,006 reviews) We stayed during the blizzard of 2026, so it may have been a harder time to keep everything clean, but the carpets on the stairs and in the hallways were very dirty, and the door to our bathroom wasn’t wiped down. Breakfast was good if you steered clear of the eggs and home fries and just stuck to ... Reviewed on Mar 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F10%2F2026&endDate=3%2F11%2F2026&selected=38357891&PinnedHotelID=38357891&HadPinnedHotel=true®ionId=183338) [See all 6,045 properties in Osterville](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F10%2F2026&endDate=3%2F11%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://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