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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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $950, price is now $605 per person
$605
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,614, price is now $689 per person
$689
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,563, price is now $820 per person
$820
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
Save 100% on your flight
Price was $1,362, price is now $769 per person
$769
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,314, price is now $766 per person
$766
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Grand Case Beach and Green Cay are located nearby.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,690, price is now $997 per person
$997
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Save 100% on your flight
Price was $1,077, price is now $683 per person
$683
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,236, price is now $814 per person
$814
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.

Cole Bay Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,186, price is now $749 per person
$749
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,073, price is now $814 per person
$814
per person
May 29 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,563, price is now $820 per person
$820
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
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 $1,362, price is now $769 per person
$769
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,044, price is now $587 per person
$587
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,768, price is now $630 per person
$630
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $1,310, price is now $762 per person
$762
per person
Jul 8 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Save 100% on your flight
Price was $1,690, price is now $997 per person
$997
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)

Top Flight Deals

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

Spirit Airlines
Sun, May 3 - Sat, May 9
LGA
LaGuardia
SXM
Princess Juliana Intl.
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, May 3 from LaGuardia to Princess Juliana Intl., returning Sat, May 9, priced at $264 found 1 day ago
American Airlines
Tue, May 19 - Fri, May 29
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$277 Roundtrip, found 6 hours ago
$277
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, May 19 from Logan Intl. to Princess Juliana Intl., returning Fri, May 29, priced at $277 found 6 hours ago
Spirit Airlines
Sun, May 3 - Sat, May 9
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, May 3 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Sat, May 9, priced at $300 found 1 day ago
Spirit Airlines
Sun, May 17 - Thu, May 21
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$301 Roundtrip, found 1 day ago
$301
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, May 17 from Philadelphia Intl. to Princess Juliana Intl., returning Thu, May 21, priced at $301 found 1 day ago