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.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hyannis (HYA)
9.4/10 Exceptional! (1,002 reviews)
My friend and I loved this property. It had an elegant yet simple and relaxed feel about it.

Reviewed on Aug. 15, 2025

Chapter House

Chapter House

3.5 out of 5
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.2/10 Wonderful! (155 reviews)
Really enjoyed the bar, which was a great spot for a late afternoon drink before dinner

Reviewed on Aug. 2, 2025

Hyannis Inn

Hyannis Inn

2 out of 5
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
8.6/10 Excellent! (1,001 reviews)
Property is beautiful, friendly staff, clean rooms.

Reviewed on Aug. 14, 2025

Heritage House Inn on Cape Cod

Heritage House Inn on Cape Cod

2.5 out of 5
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
7.4/10 Good! (128 reviews)
Overall good experience for the night and very conveniently located, I would book here again.

Reviewed on Aug. 14, 2025

Hyannis Harbor Hotel

Hyannis Harbor Hotel

3.5 out of 5
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hyannis (HYA)
8/10 Very Good! (1,005 reviews)
It was nice. Women at front desk were rude.

Reviewed on Aug. 7, 2025

Ready to book your vacation to Osterville?

 

Choose your dates

Osterville Hotel Deals

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 $253 per night from Aug 25 to Aug 26
CA $253
CA $369 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (270 reviews)
"Food was good, very clean, would definitely recommend, great place to stay"

Reviewed on Aug. 13, 2025

Margaritaville Resort Cape Cod
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 $128 per night from Sep 15 to Sep 16
CA $128
CA $161 total
Sep 15 - Sep 16
includes taxes & fees
6.8/10 (848 reviews)
"I highly recommend it, I've been there for about 3 or 4 times, always very clean!"

Reviewed on Aug. 15, 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 $198 per night from Sep 1 to Sep 2
CA $198
CA $248 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Restaurant right next door. Convenient breakfast. Easy check in and out. Good customer service- quick resolve of missing towels. Bathroom showerhead height too short- had to bend to wash hair. Overall good experience."

Reviewed on Aug. 12, 2025

Falmouth Inn
See all 6,393 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
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Frequently asked questions

How much does an Osterville vacation package cost?
Offering great value package deals from CA $1,414 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.