
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 Travel Inn
Price was CA $966, price is now CA $844 per person
CA $844
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.6/10 Exceptional! (1,000 reviews)
We loved our stay! The staff always went above and beyond to make, not just our time at the Inn comfortable, but to see that our whole trip was wonderful.
Reviewed on May 30, 2026

Inn on Main
Price was CA $1,921, price is now CA $1,528 per person
CA $1,528
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) 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 $3,101, price is now CA $2,685 per person
CA $2,685
per person
Aug 1 - Aug 6
found 18 hours ago
Roundtrip flight included
Ottawa (YOW) to Hyannis (HYA)
9.4/10 Exceptional! (1,007 reviews)
Excellent hotel stay at Anchor In. Upon arrival, the front desk team was very kind in making recommendations for restaurants and activities in the area, and gave us a wonderful room with a view of the waterfront. Parking was easy, and the property was clean.
Once in the room, it had all of the features expected, in room coffee, fridge, safe, plenty of shampoo, soap, etc. The TV had so many channels that it was challenging to keep track of all the options. The Wi-Fi connection worked well throughout our stay.
Continental breakfast was well stocked and complimentary - a great way to start each day. With beautiful views, excellent staff, and accessibility to the ferries another attractions in Hyannis, this is an incredible place to stay.
Reviewed on May 31, 2026

Wequassett Resort and Golf Club
Price was CA $5,982, price is now CA $5,231 per person
CA $5,231
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Hyannis (HYA)
9.4/10 Exceptional! (248 reviews)
From housekeeping to the front desk, the best service I've ever had.
Reviewed on Apr 26, 2026

Margaritaville Resort Cape Cod
Price was CA $3,381, price is now CA $3,013 per person
CA $3,013
per person
Aug 1 - Aug 6
found 16 hours ago
Roundtrip flight included
Ottawa (YOW) to Hyannis (HYA)
8.8/10 Excellent! (577 reviews)
First time attending Margaritaville with my family for my son’s birthday and it was amazing. The water park experience was great. Unfortunately it was raining so we were unable to use the outdoor pool. Loved the s’mores setup they had for guest to cozy up next to the fireplace with a delicious treat. The outdoor space was relaxing and I loved that they had game setup outside for kids and adults. All and all my kids really enjoyed the stay, from my 11 year old birthday boy to my 23 year old. The island vibes, along with the friendly and welcoming staff really elevated our experience! I would definitely recommend and I plan to return with my family and friends.
Reviewed on May 30, 2026
Osterville Hotel Deals

Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Jun 4 to Jun 5
CA $207
CA $237 total
Jun 4 - Jun 5
includes taxes & fees
8.6/10 Excellent! (239 reviews)
"The bed had lots of hair, and the bathroom was dangerous for your head and eyes."
Reviewed on May 31, 2026

Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $419 per night from Jun 17 to Jun 18
CA $419
CA $559 total
Jun 17 - Jun 18
includes taxes & fees
7.8/10 Good! (291 reviews)
"Check in was chaotic. I’m the staff called the room phone at 11:05pm stating they needed me to come back to the front desk for additional information. I asked the manager why they would call and wake me and my young child up past 11 pm for a reservation that had been paid for weeks in advance. They ..."
Reviewed on May 31, 2026

Bayside Resort Hotel
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $236 per night from Jun 7 to Jun 8
CA $236
CA $286 total
Jun 7 - Jun 8
includes taxes & fees
8.8/10 Excellent! (1,530 reviews)
"Whilst this hotel was extremely clean, spacious and had a brilliant pool and beach area it is extremely dated. The hallway smelt, the decor is dark brown and awful pine furniture. There was no safe in the bedrooms which as a non US traveller is a must. Only 2 towels were provided for 3 people, no ..."
Reviewed on May 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.







