Title: Osterville Vacation Packages 2026 from $450 | 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 $450 ## 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 Travel Inn](https://images.trvl-media.com/lodging/2000000/1380000/1379200/1379109/fe11d49f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyannis Travel Inn $450 per person Jun 28 - Jul 2 found 1 day ago Roundtrip flight included New York (NYC) to Hyannis (HYA) 9.6/10 Exceptional! (1,000 reviews) Didn't need air conditioning Reviewed on Apr 6, 2026 ![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 $720 per person Jun 1 - Jun 6 found 1 day 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 ![Wequassett Resort and Golf Club](https://images.trvl-media.com/lodging/1000000/10000/3700/3689/ce420299_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wequassett Resort and Golf Club Save 100% on your flight $2,616 per person Jun 25 - Jun 29 found 19 hours ago Roundtrip flight included Chicago (CHI) to Hyannis (HYA) 9.4/10 Exceptional! (245 reviews) The staff is amazing, they are kind and always looking for ways to help and make you feel welcome. Reviewed on Jan 1, 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 Save 100% on your flight $5,140 per person Jul 2 - Jul 6 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Hyannis (HYA) No reviews ![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 $1,018 per person Jun 25 - Jun 29 found 19 hours ago Roundtrip flight included Chicago (CHI) to Hyannis (HYA) 8.6/10 Excellent! (477 reviews) We had an excellent stay! The decor and cleanli ess Reviewed on Apr 6, 2026 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/2026-05-07/2026-05-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PVC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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 $179 nightly $205 total May 3 - May 4 Total with taxes and fees 8.6/10 Excellent! (521 reviews) We had an excellent stay! The decor and cleanli ess Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=5%2F3%2F2026&endDate=5%2F4%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 $134 nightly $153 total Apr 26 - Apr 27 Total with taxes and fees 8.8/10 Excellent! (1,546 reviews) Clean room, great breakfast and cozy Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=896697&PinnedHotelID=896697&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 $119 nightly $134 total Apr 12 - Apr 13 Total with taxes and fees 8/10 Very Good! (1,001 reviews) Clean room. Pleasant staff Reviewed on Mar 30, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=893142&PinnedHotelID=893142&HadPinnedHotel=true®ionId=183338) [See all 6,145 properties in Osterville](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F8%2F2026&endDate=4%2F9%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) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](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