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.
Chapter House
Price was CA $1,038, price is now CA $805 per person
CA $805
per person
May 21 - May 24
found 24 hours 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
Anchor In Distinctive Waterfront Lodging
Price was CA $1,227, price is now CA $946 per person
CA $946
per person
May 21 - May 24
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (1,000 reviews)
We were just there for 1 night. The staff was super sweet and the view was incredible!
Reviewed on Apr 8, 2026
Heritage House Inn on Cape Cod, an Ascend Collection Hotel
Price was CA $1,262, price is now CA $1,002 per person
CA $1,002
per person
Jun 8 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
8.4/10 Very Good! (20 reviews)
Great staff. Really friendly and helpful. Room was spacious and clean. Close to Main Street. I would definitely stay again the next time we visit cape cod!
Reviewed on Sep 11, 2025
Wequassett Resort and Golf Club
Price was CA $1,946, price is now CA $1,580 per person
CA $1,580
per person
May 21 - May 24
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (245 reviews)
The staff is amazing, they are kind and always looking for ways to help and make you feel welcome.
Reviewed on Jan 1, 2026
Osterville Hotel Deals
Margaritaville Resort Cape Cod
1225 Iyannough Rd Hyannis MA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from May 3 to May 4
CA $174
CA $277 total
May 3 - May 4
includes taxes & fees
8.6/10 Excellent! (537 reviews)
.
Reviewed on Apr 16, 2026
Bayside Resort Hotel
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Apr 26 to Apr 27
CA $151
CA $189 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (1,554 reviews)
The breakfast choices are surprisingly vast and yummy. The pool is heated and very pleasant. Overall, I'd definitely recommend this hotel for a stay in Cape Cod; and it's just a 40 min drive up the peninsula to quaint Provincetown.
Reviewed on Apr 16, 2026
Falmouth Inn
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Apr 22 to Apr 23
CA $136
CA $183 total
Apr 22 - Apr 23
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Clean room. Pleasant staff
Reviewed on Mar 30, 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.
