Search Deals onOld Man Bay Vacation Packages
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Old Man Bay Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
ONE Canal Point
Price was $1,292, price is now $932 per person
$932
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star aparthotel in Seven Mile Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Galleon Villas by Hello Cayman Vacation
Save 100% on your flight
Price was $2,479, price is now $1,465 per person
$1,465
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star beach villa in Seven Mile Beach. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Kimpton Seafire Resort + Spa by IHG
Save 100% on your flight
Price was $1,995, price is now $1,229 per person
$1,229
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 5-star luxury hotel in Seven Mile Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Wyndham Reef Resort Grand Cayman
Save 100% on your flight
Price was $1,581, price is now $1,049 per person
$1,049
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star beach resort in East End. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Colliers Public Beach and Barefoot Beach are located nearby.
Cayman Luxury Rentals at Sunset Cove
Save 100% on your flight
Price was $3,854, price is now $2,616 per person
$2,616
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star beach condo in Seven Mile Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
Grand Cayman Marriott Resort
Save 100% on your flight
Price was $1,711, price is now $1,221 per person
$1,221
per person
Nov 17 - Nov 21
found 9 hours ago
Roundtrip non-stop flight included
Nashville (BNA) to George Town (GCM)
Stay at this 4.5-star luxury resort in Seven Mile Beach. Enjoy free parking, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Port of Georgetown and Seven Mile Beach are located nearby.
Black Urchin
Save 100% on your flight
Price was $11,372, price is now $8,212 per person
$8,212
per person
Oct 25 - Nov 1
found 13 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 4.5-star luxury hotel in Bodden Town. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Boddentown Art Shop and Mission House are located nearby.
Governors Village Seven Mile Beach Corridor
Price was $1,390, price is now $1,011 per person
$1,011
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to George Town (GCM)
Stay at this 3.5-star family-friendly apartment in Seven Mile Beach. Enjoy free parking, a 24-hour fitness center, and a garden. Popular attractions Seven Mile Beach and Port of Georgetown are located nearby.
Old Man Bay Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Old Man Bay 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.
Sat, Nov 1 - Sat, Nov 8
BOS
Logan Intl.
GCM
Owen Roberts Intl.
$280 Roundtrip, found 14 hours ago
$280
Roundtrip
found 14 hours ago
Sun, Sep 21 - Mon, Sep 29
ORD
O'Hare Intl.
GCM
Owen Roberts Intl.
$360 Roundtrip, found 2 days ago
$360
Roundtrip
found 2 days ago
Wed, Dec 3 - Tue, Dec 9
PHL
Philadelphia Intl.
GCM
Owen Roberts Intl.
$379 Roundtrip, found 5 hours ago
$379
Roundtrip
found 5 hours ago
Sat, Apr 18 - Tue, Apr 21
LGA
LaGuardia
GCM
Owen Roberts Intl.
$387 Roundtrip, found 6 days ago
$387
Roundtrip
found 6 days ago
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