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.
Hyannis Host Inn
Price was CA $898, price is now CA $765 per person
CA $765
per person
Jul 29 - Aug 2
found 5 hours ago
Roundtrip flight included
Montreal (YUL) to Hyannis (HYA)
7.8/10 Good! (457 reviews)
The air conditioning was working good and the mall was on the same street so it was good
Reviewed on Oct 12, 2025
Anchor In Distinctive Waterfront Lodging
Price was CA $1,782, price is now CA $1,352 per person
CA $1,352
per person
Jul 29 - Aug 2
found 5 hours ago
Roundtrip flight included
Montreal (YUL) to Hyannis (HYA)
9.4/10 Exceptional! (1,007 reviews)
Highly recommend. Check in was great and nice to be given the lay of the land. Amenities were plentiful. The room was very clean and well appointed. Location was perfect for the ferries and Main Street. Would definitely stay here again.
Reviewed on May 19, 2026
Inn on Main
Price was CA $1,771, price is now CA $1,419 per person
CA $1,419
per person
Jul 29 - Aug 2
found 5 hours ago
Roundtrip flight included
Montreal (YUL) to Hyannis (HYA)
10/10 Exceptional! (74 reviews)
The Inn is beautifully restored and decorated tastefully by owners. They have thought of many details and welcome suggestions for more. Breakfast is always interesting and delicious. Owners Sarah and Chris (and welcome dog, Crocker) are welcoming, helpful and engaging. No reason to go anywhere else!
Reviewed on Dec 26, 2025
Margaritaville Resort Cape Cod
Price was CA $1,752, price is now CA $1,500 per person
CA $1,500
per person
Jul 29 - Aug 2
found 5 hours ago
Roundtrip flight included
Montreal (YUL) to Hyannis (HYA)
8.8/10 Excellent! (577 reviews)
Gorgeous hotel, very clean and welcoming. We had a wonderful stay, staff was very kind.
Reviewed on May 13, 2026
Osterville Hotel Deals
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from May 31 to Jun 1
CA $247
CA $362 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (584 reviews)
"Great place to spend a night or weekend with the kids"
Reviewed on May 25, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jun 1 to Jun 2
CA $180
CA $206 total
Jun 1 - Jun 2
includes taxes & fees
8.6/10 Excellent! (234 reviews)
"Staff was friendly, amenities were nice, room was cozy."
Reviewed on May 23, 2026
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
867 Iyannough Road Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from May 31 to Jun 1
CA $234
CA $268 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (708 reviews)
"The rooms are cleaned every other day. The rooms should be cleaned every day. The breakfast was just ok. The choices were limited. The breakfast area should be cleaned often especially when there are a lot of children staying at the hotel. The room was cold. We had to call a couple of times before ..."
Reviewed on May 25, 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.
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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.
