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 $736
per person
Nov 25 - Nov 28
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
8.6/10 Excellent! (143 reviews)
Enjoyed my stay, except walls very thin and even the rain was super loud. Stay on 1st or 2nd floor, away from the main road. Terrific staff. Nice spacious room with great amenities.
Reviewed on Oct 12, 2026
Inn on Main
CA $1,160
per person
Nov 25 - Nov 28
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
10/10 Exceptional! (80 reviews)
Ruta and David were excellent hosts. The Inn is lovely and has a beautiful yard with outdoor seating. The rooms were very clean, spacious and well appointed. The breakfasts were outstanding. The Inn is in a great location for exploring the Cape. I would highly recommend a visit to the Inn on Main.
Reviewed on Sep 27, 2026
Anchor In Distinctive Waterfront Lodging
CA $824
per person
Nov 25 - Nov 28
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.4/10 Exceptional! (1,005 reviews)
Great experience from the helpful front desk to the view of the bay. Good breakfast with a personal touch by a very friendly and helpful lady . Clean room and well kept public areas The occasional ferry horn added to a real Cape Cod feel. While everything is updated and modern this property had the atmosphere of a pleasant step back in time. Highly recommend. Note: There is no elevator to the second floor.
Reviewed on Oct 14, 2026
Margaritaville Resort Cape Cod
CA $1,097
per person
Nov 25 - Nov 28
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
8.6/10 Excellent! (784 reviews)
Didn’t like the room next to the pool, especially on the first floor. No privacy. No fresh air. No sunlight. Had a damp feeling in the room the whole week. But we did like Nate the bar tender!
Reviewed on Oct 16, 2026
Ready to book your vacation to Osterville?
Osterville Hotel Deals
Inn on the Square
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
CA $170
CA $230 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Very helpful & friendly staff. Walkable to stores & Restaurants."
Reviewed on Oct 14, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
CA $159
CA $263 total
Nov 1 - Nov 2
includes taxes & fees
7.6/10 Good! (534 reviews)
"Beautiful location! Our stay was just overnight so didn’t get to enjoy it to its fullest."
Reviewed on Oct 16, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
CA $173
CA $198 total
Nov 18 - Nov 19
includes taxes & fees
8.4/10 Very good! (429 reviews)
"Wall paper on floor, bannisters left over a week on the floor to trip over and studs to fix bannisters dangerously sticking out of wall. Room numbers were written on paper, stuck to wall with sticky tape, easily moved around by mischievous tenants. Carpets up in places, very dirty carpets in some ..."
Reviewed on Oct 16, 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 $736 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.
