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.
Inn on Main
Price was CA $1,571, price is now CA $1,140 per person
CA $1,140
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Anchor In Distinctive Waterfront Lodging
Price was CA $1,557, price is now CA $1,144 per person
CA $1,144
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (1,005 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
Chapter House
Price was CA $1,449, price is now CA $1,152 per person
CA $1,152
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.2/10 Wonderful! (162 reviews)
This property was clean and well maintained. There was ample parking and the staff was very friendly.
Reviewed on Sep 26, 2025
Margaritaville Resort Cape Cod
Price was CA $1,498, price is now CA $1,220 per person
CA $1,220
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
8.8/10 Excellent! (567 reviews)
Gorgeous hotel, very clean and welcoming. We had a wonderful stay, staff was very kind.
Reviewed on May 13, 2026
Wequassett Resort and Golf Club
Price was CA $4,429, price is now CA $3,655 per person
CA $3,655
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (247 reviews)
From housekeeping to the front desk, the best service I've ever had.
Reviewed on Apr 26, 2026
Osterville Hotel Deals
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from May 31 to Jun 1
CA $233
CA $345 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (578 reviews)
"Gorgeous hotel, very clean and welcoming. We had a wonderful stay, staff was very kind."
Reviewed on May 13, 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 $232 per night from May 31 to Jun 1
CA $232
CA $266 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (704 reviews)
"Easy location. Room was clean. Breakfast had lots of options."
Reviewed on May 19, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from May 31 to Jun 1
CA $233
CA $345 total
May 31 - Jun 1
includes taxes & fees
8/10 Very Good! (280 reviews)
"The hotel has an excellent location . They were understaffed. We arrived at 6:00 PM and check in was at 4:00 PM. We were told that they were still cleaning our room . The room was finally ready at 8:00 PM. W e had to change our dinner plans due to this. The staff did not seem to care much , they ..."
Reviewed on May 19, 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.
