Search Deals on
Cole Bay Vacation Packages

Build your package with 2 more options

Cole Bay Flight + Hotel Packages

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
Price was $1,093, price is now $695 per person
$695
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Price was $1,726, price is now $740 per person
$740
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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
Save 100% on your flight
Price was $1,631, price is now $777 per person
$777
per person
Aug 24 - Aug 28
found 14 hours 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.
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Price was $1,432, price is now $945 per person
$945
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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.
Hotel La Plantation

Hotel La Plantation

4 out of 5
Price was $1,067, price is now $727 per person
$727
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Philipsburg (SXM)
Book a stay at this beach hotel in Orient Bay. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Grand Case Beach and Orient Bay are located nearby.
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was $1,168, price is now $807 per person
$807
per person
Aug 6 - Aug 10
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.
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was $1,195, price is now $846 per person
$846
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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 helpful staff in our reviews. Popular attractions Grand Case Beach and Mont Vernon are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Price was $994, price is now $712 per person
$712
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) 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.

Cole Bay Vacation Packages 3-4 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
Price was $1,007, price is now $684 per person
$684
per person
Aug 6 - Aug 10
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
Price was $1,507, price is now $686 per person
$686
per person
Aug 6 - Aug 10
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
Save 100% on your flight
Price was $1,631, price is now $777 per person
$777
per person
Aug 24 - Aug 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,279, price is now $878 per person
$878
per person
Aug 6 - Aug 10
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
Price was $1,093, price is now $695 per person
$695
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Philipsburg (SXM)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was $1,726, price is now $740 per person
$740
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $2,031, price is now $930 per person
$930
per person
Aug 15 - Aug 20
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Panorama Residences at Monte Vista

Panorama Residences at Monte Vista

4.5 out of 5
Point Blanche
Price was $1,432, price is now $945 per person
$945
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Albany (ALB) to Philipsburg (SXM)

Top Flight Deals

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

American Airlines
Sun, Aug 16 - Wed, Sep 2
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$371 Roundtrip, found 1 day ago
$371
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Aug 16 from Logan Intl. to Princess Juliana Intl., returning Wed, Sep 2, priced at $371 found 1 day ago
JetBlue Airways
Sun, Jun 21 - Wed, Jun 24
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$382 Roundtrip, found 6 days ago
$382
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, Jun 21 from John F. Kennedy Intl. to Princess Juliana Intl., returning Wed, Jun 24, priced at $382 found 6 days ago
American Airlines
Sat, Aug 1 - Thu, Aug 6
LGA
LaGuardia
SXM
Princess Juliana Intl.
$392 Roundtrip, found 4 days ago
$392
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Aug 1 from LaGuardia to Princess Juliana Intl., returning Thu, Aug 6, priced at $392 found 4 days ago
American Airlines
Thu, Dec 10 - Sun, Dec 13
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$395 Roundtrip, found 1 day ago
$395
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Dec 10 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Sun, Dec 13, priced at $395 found 1 day ago