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Osterville Vacation Packages

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Osterville Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Villa Callo Inn

The Villa Callo Inn

3 out of 5
Price was $1,079, price is now $1,010 per person
$1,010
per person
Oct 8 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Stay at this B&B in West Harwich. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cape Cod Theatre Company – Home of the Harwich Jr. Theatre and Swan Pond are located nearby.
Good

Reviewed on Aug 29, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
Save 100% on your flight
Price was $3,554, price is now $2,848 per person
$2,848
per person
Oct 8 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Book a stay at this luxury resort in Harwich. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Caleb Nickerson House and Captains Golf Course are located nearby.

Inn on Main

Inn on Main

3.5 out of 5
Price was $1,227, price is now $1,067 per person
$1,067
per person
Oct 8 - Oct 12
found 13 hours ago
Roundtrip 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 Main Street Hyannis are located nearby.
Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend

Reviewed on Aug 8, 2026

Hyannis Host Inn

Hyannis Host Inn

2 out of 5
Price was $1,426, price is now $1,342 per person
$1,342
per person
Oct 15 - Oct 19
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular attractions Main Street Hyannis and Hyannis Harbor are located nearby.

Courtyard Resort

Courtyard Resort

2 out of 5
Price was $1,464, price is now $1,384 per person
$1,384
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hyannis (HYA)
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and a garden. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
No breakfast. Very clean & quiet. Front desk very helpful. I had to ask for the ironing board and the blow dryer. Other than that, everything was perfect great location close to everything within walking distance to Main St stores.

Reviewed on Aug 26, 2026

Courtyard By Marriott Cape Cod Hyannis

Courtyard By Marriott Cape Cod Hyannis

3 out of 5
Price was $1,750, price is now $1,654 per person
$1,654
per person
Oct 15 - Oct 19
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Main Street Hyannis and Cape Cod Melody Tent are located nearby.
Location was good and relaxing

Reviewed on Sep 5, 2026

Holiday Inn Hyannis by IHG

Holiday Inn Hyannis by IHG

3 out of 5
Price was $1,545, price is now $1,478 per person
$1,478
per person
Oct 15 - Oct 19
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
Stay at this hotel in Hyannis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Cape Cod Melody Tent and Main Street Hyannis are located nearby.

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $1,632, price is now $1,563 per person
$1,563
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Cape Cod Melody Tent are located nearby.
My wife and I chose Hyannis and the Anchor In Hotel for its location close to the airport, the village ($12.00Uber fare) and walking distance to all the tour boats and ferry’s to the islands. There are two popular restaurants in the adjacent marina and a small beach nearby for watching the sun set. The pool is nice and the staff friendly and helpful.

Reviewed on Sep 6, 2026

Osterville Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Villa Callo Inn

The Villa Callo Inn

3 out of 5
Price was $1,079, price is now $1,010 per person
$1,010
per person
Oct 8 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
Save 100% on your flight
Price was $3,554, price is now $2,848 per person
$2,848
per person
Oct 8 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Inn on Main

Inn on Main

3.5 out of 5
Price was $1,227, price is now $1,067 per person
$1,067
per person
Oct 8 - Oct 12
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Hyannis Host Inn

Hyannis Host Inn

2 out of 5
Price was $1,426, price is now $1,342 per person
$1,342
per person
Oct 15 - Oct 19
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)

Osterville Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $1,580, price is now $1,422 per person
$1,422
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hyannis (HYA)
Inn on Main

Inn on Main

3.5 out of 5
Price was $1,885, price is now $1,644 per person
$1,644
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hyannis (HYA)
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $1,713, price is now $1,537 per person
$1,537
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hyannis (HYA)
The Villa Callo Inn

The Villa Callo Inn

3 out of 5
Price was $1,784, price is now $1,693 per person
$1,693
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hyannis (HYA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Wed, Sep 30 - Tue, Oct 6
DCA
Ronald Reagan Washington National
ACK
Nantucket Memorial
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 30 from Ronald Reagan Washington National to Nantucket Memorial, returning Tue, Oct 6, priced at $250 found 1 day ago
American Airlines
Sun, Nov 1 - Tue, Nov 3
IAD
Washington Dulles Intl.
ACK
Nantucket Memorial
$855 Roundtrip, found 6 days ago
$855
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Nov 1 from Washington Dulles Intl. to Nantucket Memorial, returning Tue, Nov 3, priced at $855 found 6 days ago
American Airlines
Tue, Sep 8 - Tue, Sep 8
LGA
LaGuardia
MVY
Martha's Vineyard
$918 Roundtrip, found 3 days ago
$918
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Sep 8 from LaGuardia to Martha's Vineyard, returning Tue, Sep 8, priced at $918 found 3 days ago
Cape Air
Wed, Sep 9 - Wed, Sep 9
JFK
John F. Kennedy Intl.
MVY
Martha's Vineyard
$933 Roundtrip, found 22 hours ago
$933
Roundtrip
found 22 hours ago
Select Cape Air flight, departing Wed, Sep 9 from John F. Kennedy Intl. to Martha's Vineyard, returning Wed, Sep 9, priced at $933 found 22 hours ago