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Cole Bay Vacation Packages

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Cole Bay Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,621, price is now $939 per person
$939
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $2,806, price is now $1,397 per person
$1,397
per person
Apr 28 - May 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $2,172, price is now $1,264 per person
$1,264
per person
Apr 28 - May 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this family-friendly hotel in Oyster Pond. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Case Beach and Dawn Beach are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $1,665, price is now $1,011 per person
$1,011
per person
Apr 28 - May 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this beach resort in Oyster Pond. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Grand Case Beach and Oyster Bay Marina are located nearby.
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $2,332, price is now $1,471 per person
$1,471
per person
Apr 28 - May 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this beach resort in Philipsburg. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $2,398, price is now $1,524 per person
$1,524
per person
Apr 28 - May 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this luxury aparthotel in Philipsburg. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Maho Beach and Harbour Point Village are located nearby.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $2,741, price is now $1,858 per person
$1,858
per person
Apr 28 - May 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this spa resort in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the restaurant in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
Price was $1,391, price is now $973 per person
$973
per person
Apr 28 - May 6
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Book a stay at this beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.

Cole Bay Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was $1,225, price is now $883 per person
$883
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,290, price is now $1,178 per person
$1,178
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Save 100% on your flight
Price was $1,621, price is now $939 per person
$939
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Philipsburg (SXM)
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was $1,418, price is now $896 per person
$896
per person
Apr 6 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

Cole Bay Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Save 100% on your flight
Price was $1,336, price is now $723 per person
$723
per person
May 8 - May 13
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $2,325, price is now $1,032 per person
$1,032
per person
May 11 - May 18
found 24 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,802, price is now $823 per person
$823
per person
May 8 - May 13
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,434, price is now $872 per person
$872
per person
May 8 - May 13
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Philipsburg (SXM)

Top Flight Deals

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

Spirit Airlines
Thu, May 7 - Sat, May 9
FLL
Fort Lauderdale - Hollywood Intl.
SXM
Princess Juliana Intl.
$246 Roundtrip, found 3 days ago
$246
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, May 7 from Fort Lauderdale - Hollywood Intl. to Princess Juliana Intl., returning Sat, May 9, priced at $246 found 3 days ago
American Airlines
Fri, May 8 - Tue, May 12
MIA
Miami Intl.
SXM
Princess Juliana Intl.
$275 Roundtrip, found 3 days ago
$275
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, May 8 from Miami Intl. to Princess Juliana Intl., returning Tue, May 12, priced at $275 found 3 days ago
Delta
Tue, Mar 10 - Wed, Mar 11
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$302 Roundtrip, found 4 days ago
$302
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Mar 10 from Logan Intl. to Princess Juliana Intl., returning Wed, Mar 11, priced at $302 found 4 days ago
United
Fri, Apr 10 - Wed, Apr 15
YYZ
Pearson Intl.
SXM
Princess Juliana Intl.
$307 Roundtrip, found 6 days ago
$307
Roundtrip
found 6 days ago
Select United flight, departing Fri, Apr 10 from Pearson Intl. to Princess Juliana Intl., returning Wed, Apr 15, priced at $307 found 6 days ago