Osterville Vacation Packages

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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.

Top Osterville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was CA $1,192, price is now CA $948 per person
CA $948
per person
Aug 27 - Aug 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
8.8/10 Excellent! (609 reviews)
Indoor water pools should open earlier than 3pm. Closes at 8

Reviewed on Jul 8, 2026

Inn on Main

Inn on Main

3.5 out of 5
Price was CA $1,504, price is now CA $1,317 per person
CA $1,317
per person
Aug 27 - Aug 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
10/10 Exceptional! (75 reviews)
I cannot recommend this property enough. David and Ruta are amazing hosts. They are so considerate and helpful. Breakfast is wonderful and they are more than willing to accommodate any dietary needs. The property is beautiful and well maintained. They have drawers full of travel supplies, and there are fresh baked cookies every day, in your room! The Inn is very well situated and walkable to some good restaurants (plan ahead to have dinner at the Old Yarmouth Inn). The Inn on Main is really not to be missed. Thank you for the amazing weekend!

Reviewed on Jun 22, 2026

Chapter House

Chapter House

3.5 out of 5
Price was CA $1,231, price is now CA $1,094 per person
CA $1,094
per person
Aug 27 - Aug 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.2/10 Wonderful! (172 reviews)
On the postive side, the interior of the Inn is very pretty and well maintained. We were given an early check-in, which was much appreciated. Our room in the Carriage House was clean and the bed was comfortable. We enjoyed the patio out back each night of our 3 night stay. The Old Yarmouth Inn and Leonessa were both wonderful restaurants less than 1 mile from the Inn. On the negative side, although 2 reviews featured on the Inn's website rave about the breakfast, breakfast is no longer served. We did not get the room we booked. Our room was extremely small, with bunk beds, instead of a sofa, no night table on one side, and wires from the tv and AC hanging across the wall. The smoke detector went off from the steam every time we showered. The exterior of the property and landscaping is in need of much TLC. Although we could have reached the host by text if we needed something, we did not see them after check-in, nor did they reach out during our 3 night stay.

Reviewed on Jul 6, 2026

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was CA $1,483, price is now CA $1,331 per person
CA $1,331
per person
Aug 27 - Aug 30
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (1,002 reviews)
Amazing staff

Reviewed on Jul 5, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
Price was CA $7,994, price is now CA $7,582 per person
CA $7,582
per person
Aug 14 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.4/10 Exceptional! (258 reviews)
Everything is nice Bed was not comfortable Not a great value, but nice place

Reviewed on Jul 1, 2026

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Osterville Hotel Deals

Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Jul 19 to Jul 20
CA $343
CA $392 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (280 reviews)
"I believe they were understaffed. Person handling breakfast shift could not keep up. Ran out of dishes constantly and new plates/silverware put out were dirty. Staff at front desk left shift late at night and were already back mid morning the next day. It appeared they may be remodeling as I could ..."

Reviewed on Jul 7, 2026

Iris Hotel Cape Cod
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $363 per night from Jul 15 to Jul 16
CA $363
CA $497 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (618 reviews)
"Indoor water pools should open earlier than 3pm. Closes at 8"

Reviewed on Jul 8, 2026

Margaritaville Resort Cape Cod
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $594 per night from Jul 26 to Jul 27
CA $594
CA $761 total
Jul 26 - Jul 27
includes taxes & fees
7.8/10 Good! (351 reviews)
"Great location"

Reviewed on Jul 9, 2026

Sea Crest Beach Resort
See all 6,434 properties in Osterville
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Stay near popular Osterville attractions

A wooden pier with a sunset view over the water.

Dowses Beach

10.0/10 (1 review)
Why not spend a lazy afternoon at Dowses Beach during your trip to Osterville?
See properties

Frequently asked questions

How much does an Osterville vacation package cost?
Offering great value package deals from CA $948 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?

  1. Choose your travel dates: What you plan to do in Osterville and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the right Osterville vacation package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.