Search Deals onOsterville Vacation Packages
Osterville Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Courtyard Resort
Price was $666, price is now $603 per person
$603
per person
Oct 8 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and a garden. Popular attractions Main Street Hyannis and Hyannis Harbor are located nearby.
Anchor In Distinctive Waterfront Lodging
Price was $731, price is now $604 per person
$604
per person
Sep 18 - Sep 20
found 22 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Hyannis (HYA)
Stay at this hotel in Hyannis. Enjoy free WiFi, an outdoor pool, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
The hotel staff were extremely accommodating- ready to help right away with any minor issue we had during our stay! Very clean, although a bathroom update would be nice- the patio was nice for just relaxing and taking in the view. I would highly recommend.
Reviewed on Jul 27, 2026
Inn on Main
Price was $755, price is now $666 per person
$666
per person
Sep 18 - Sep 20
found 22 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Hyannis (HYA)
Stay at this B&B in Yarmouth Port. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mayflower Beach and Cape Cod Inflatable Park are located nearby.
The room was cozy, clean, and comfortable, and the breakfast each day was unique and delicious! Hosts are so friendly, helpful, and communicative! They felt like friends when we left! 10/10 recommend!!
Reviewed on Jul 27, 2026
Chapter House
Price was $694, price is now $615 per person
$615
per person
Sep 18 - Sep 20
found 22 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Hyannis (HYA)
Book a stay at this historic guesthouse in Yarmouth Port. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Mayflower Beach and Cape Cod Inflatable Park are located nearby.
The grounds on the property are beautiful. It is centrally located to explore the beaches and neighboring towns. Did not like that the inn keeper was not readily available. Had to either wait to be seen on the cameras around the house or text her. Did not have a cozy welcoming feel that we were expecting.
Reviewed on Jul 28, 2026
The Villa Callo Inn
Price was $1,252, price is now $1,121 per person
$1,121
per person
Oct 8 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
Stay at this B&B in West Harwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions West Dennis Beach and Cape Cod Inflatable Park are located nearby.
The staff were super friendly and the homemade breakfast was so good.
Reviewed on Jun 29, 2026
Holiday Inn Express Hyannis Cape Cod by IHG
Price was $786, price is now $706 per person
$706
per person
Oct 8 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
Book a stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Cape Codder Water Park and Cape Cod Melody Tent are located nearby.
The customer service was amazing; I was feeling that I was at home!
Reviewed on Jul 26, 2026
Ocean Street Inn on Hyannis Harbor
Price was $682, price is now $620 per person
$620
per person
Oct 8 - Oct 12
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
Stay at this motel in Hyannis. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Rooms were big. Hotel staff was accommodating and were able to give us 2 rooms next to each other.
Reviewed on Jul 27, 2026
Water Access 5-bed 2-bath Retreat
Price was $3,576, price is now $3,256 per person
$3,256
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Hyannis (HYA)
Stay at this vacation home in Hyannis. Enjoy free parking, a beach locale, and a garden. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
Osterville Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Osterville Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Aug 11 - Thu, Aug 20
DCA
Ronald Reagan Washington National
MVY
Martha's Vineyard
$219 Roundtrip, found 12 hours ago
$219
Roundtrip
found 12 hours ago
Tue, Aug 18 - Sat, Sep 5
ORD
O'Hare Intl.
HYA
Barnstable Municipal
$233 Roundtrip, found 1 hour ago
$233
Roundtrip
found 1 hour ago
Thu, Aug 20 - Sat, Aug 29
JFK
John F. Kennedy Intl.
MVY
Martha's Vineyard
$254 Roundtrip, just found
$254
Roundtrip
just found
Sat, Sep 26 - Wed, Oct 14
BOS
Logan Intl.
ACK
Nantucket Memorial
$260 Roundtrip, just found
$260
Roundtrip
just found
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