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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.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Price was $1,160, price is now $868 per person
$868
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Port of St. Maarten and Orient Bay are located nearby.
The staff is very friendly and accommodating. Beautiful views. The only thing I would ask is that water be restocked daily because it is easy to get dehydrated even if you buy your own water.

Reviewed on Sep 14, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was $1,924, price is now $1,003 per person
$1,003
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Great hotel

Reviewed on Sep 14, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Save 100% on your flight
Price was $1,497, price is now $872 per person
$872
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Old resort being maintained.

Reviewed on Sep 15, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,718, price is now $1,239 per person
$1,239
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 staff was nice, they were helpful with setting up taxi rides and other things. The only thing that I didn’t like was that the pool closed at 8:00 pm every night.

Reviewed on Sep 15, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,089, price is now $1,518 per person
$1,518
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Orient Bay and Grand Case Beach are located nearby.
Fabulous stay! Beautiful resort right on Orient Bay!

Reviewed on Aug 26, 2026

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Price was $1,358, price is now $993 per person
$993
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this beach hotel in Philipsburg. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Maho Beach and Port of St. Maarten are located nearby.

Divi Little Bay Beach Resort

Divi Little Bay Beach Resort

4 out of 5
Price was $1,288, price is now $976 per person
$976
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Port of St. Maarten are located nearby.

Sonesta Ocean Point All Inclusive, Adults Only Resort

Sonesta Ocean Point All Inclusive, Adults Only Resort

5 out of 5
Price was $2,927, price is now $2,281 per person
$2,281
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
Book a stay at this luxury property in Lowlands. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maho Beach and Mullet Bay Beach are located nearby.
The property appears old and a bit dated. Especially the furniture. Our bath room shower had mold on the tiled floor. Our room had a musty odor. We're not ones to complain. The staff were top notch. Names that consistly were Johnathan aka "smiley" and Rue at Azul and Maurice at the seascape swim up bar .

Reviewed on Sep 14, 2026

Cole Bay Vacation Packages 3-4 Night Stays

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
Pelican Key
Save 100% on your flight
Price was $1,497, price is now $872 per person
$872
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was $1,924, price is now $1,003 per person
$1,003
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was $1,718, price is now $1,239 per person
$1,239
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Philipsburg (SXM)
La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Save 100% on your flight
Price was $2,089, price is now $1,518 per person
$1,518
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,310, price is now $832 per person
$832
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,920, price is now $916 per person
$916
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $2,049, price is now $991 per person
$991
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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 $940 per person
$940
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philipsburg (SXM)

Top Flight Deals

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

JetBlue Airways
Mon, Oct 26 - Wed, Oct 28
JFK
John F. Kennedy Intl.
SXM
Princess Juliana Intl.
$290 Roundtrip, found 13 hours ago
$290
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Mon, Oct 26 from John F. Kennedy Intl. to Princess Juliana Intl., returning Wed, Oct 28, priced at $290 found 13 hours ago
Delta
Mon, Nov 16 - Fri, Dec 4
BOS
Logan Intl.
SXM
Princess Juliana Intl.
$295 Roundtrip, found 23 hours ago
$295
Roundtrip
found 23 hours ago
Select Delta flight, departing Mon, Nov 16 from Logan Intl. to Princess Juliana Intl., returning Fri, Dec 4, priced at $295 found 23 hours ago
United
Mon, Jan 25 - Wed, Feb 3
YYZ
Pearson Intl.
SXM
Princess Juliana Intl.
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select United flight, departing Mon, Jan 25 from Pearson Intl. to Princess Juliana Intl., returning Wed, Feb 3, priced at $309 found 2 days ago
American Airlines
Mon, Nov 2 - Thu, Nov 12
EWR
Newark Liberty Intl. Airport
SXM
Princess Juliana Intl.
$325 Roundtrip, found 4 days ago
$325
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Nov 2 from Newark Liberty Intl. Airport to Princess Juliana Intl., returning Thu, Nov 12, priced at $325 found 4 days ago