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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.
The Paradise Inn

The Paradise Inn

3 out of 5
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 3-star hotel in Philipsburg. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Orient Bay Beach and Maho 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
per person
Apr 20 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star 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 Orient Bay Beach are located nearby.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star 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 Orient Bay Beach and Orient Bay are located nearby.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
per person
Apr 3 - Apr 6
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Philipsburg (SXM)
Stay at this 4-star 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
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 3.5-star 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 Orient Bay Beach and Dawn Beach are located nearby.
Mary's Boon Beach Resort & Spa

Mary's Boon Beach Resort & Spa

3 out of 5
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 3-star beach hotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Save 100% on your flight
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star 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 Orient Bay Beach are located nearby.
Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina

4 out of 5
Save 100% on your flight
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Philipsburg (SXM)
Stay at this 4-star beach resort in Oyster Pond. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Orient Bay Beach and Orient Bay are located nearby.

Top Flight Deals

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

Frontier Airlines
Sun, Feb 23 - Mon, Mar 3
PHL
Philadelphia Intl.
SXM
Princess Juliana Intl.
$229 Roundtrip, found 2 days ago
$229
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Feb 23 from Philadelphia Intl. to Princess Juliana Intl., returning Mon, Mar 3, priced at $229 found 2 days ago
Frontier Airlines
Mon, May 12 - Mon, May 19
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$234 Roundtrip, just found
$234
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, May 12 from John F. Kennedy Intl. to Princess Juliana Intl., returning Mon, May 19, priced at $234 just found
Frontier Airlines
Mon, May 19 - Fri, May 23
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 19 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Fri, May 23, priced at $269 found 2 days ago
WestJet
Wed, Apr 16 - Fri, Apr 25
YYZ
Pearson Intl.
SXM
Princess Juliana Intl.
$299 Roundtrip, found 3 days ago
$299
Roundtrip
found 3 days ago
Select WestJet flight, departing Wed, Apr 16 from Pearson Intl. to Princess Juliana Intl., returning Fri, Apr 25, priced at $299 found 3 days ago