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.
Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod

2.5 out of 5
per person
Oct 2 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Hyannis (HYA)
7.8/10 Good! (1,000 reviews)
Food options:Hot cocoa powder and bagel could be a great breakfast option.

Reviewed on Aug. 7, 2025

Chapter House

Chapter House

3.5 out of 5
per person
Oct 2 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Hyannis (HYA)
9.2/10 Wonderful! (153 reviews)
Really enjoyed the bar, which was a great spot for a late afternoon drink before dinner

Reviewed on Aug. 2, 2025

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
per person
Oct 2 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Hyannis (HYA)
9.4/10 Exceptional! (1,005 reviews)
I have stayed at the hotel and Sandy has always been wonderful. All the staff is pleasant but she stands out! The property needs outdoor work, some weeding etc. the paint could be refreshed and some of the furnishings polished. I really like the okace

Reviewed on Aug. 7, 2025

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
per person
Oct 2 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Hyannis (HYA)
8.8/10 Excellent! (238 reviews)
I knew there would be a lot of kids and there were. That's okay it is a water park. I did not like having to pay $20 for 1pm check in. Really? Loved the Landshark Bar.

Reviewed on Aug. 7, 2025

Heritage House Inn on Cape Cod

Heritage House Inn on Cape Cod

2.5 out of 5
per person
Oct 2 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Hyannis (HYA)
7.4/10 Good! (125 reviews)
We stayed for one night and we loved it.

Reviewed on Aug. 7, 2025

Ready to book your vacation to Osterville?

 

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Osterville Hotel Deals

Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
662 Main Street, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Sep 8 to Sep 9
CA $120
CA $152 total
Sep 8 - Sep 9
includes taxes & fees
6.8/10 (828 reviews)
"The room was clean and very comfortable, and the bathroom was also immaculate with a very good shower. The TV was really easy to work and also nice and big"

Reviewed on Aug. 6, 2025

Hyannis Plaza Hotel
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Sep 1 to Sep 2
CA $186
CA $234 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,014 reviews)
"Clean"

Reviewed on Aug. 4, 2025

Falmouth Inn
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Sep 1 to Sep 2
CA $247
CA $299 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,453 reviews)
Good stay
"The bed was soft and room was nice"

Reviewed on Aug. 6, 2025

Bayside Resort Hotel
See all 6,374 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.
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Frequently asked questions

How much does an Osterville vacation package cost?
Offering great value package deals from CA $516 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.

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