Mountain Vacations in Lesser Antilles 2026

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Flight and Mountain hotel deals in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

CA $1,541

per person

Nov 1 - Nov 6

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,837

per person

Dec 5 - Dec 12

found 3 hours ago

Roundtrip flight included

Montreal (YUL) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

Ocean view was not quite true

Reviewed on Oct 2, 2026

COCOS Hotel - Adults Only - Caters to Couples - All Inclusive

Save 100% on your flight

CA $4,918

per person

Dec 10 - Dec 14

found 20 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. John's (ANU)

9.4/10 Exceptional! (857 reviews)

Esmeralda Resort

CA $1,657

per person

Nov 1 - Nov 6

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Philipsburg (SXM)

8.6/10 Excellent! (548 reviews)

The Buccaneer Beach & Golf Resort

CA $3,293

per person

Nov 4 - Nov 11

found 14 hours ago

Roundtrip flight included

Toronto (YTO) to Christiansted (STX)

9.2/10 Wonderful! (1,003 reviews)

I enjoyed the bucaneer and its rich history! Food on property was amazing!

Reviewed on Sep 30, 2026

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5* Mountain holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

Four Seasons Resort - Nevis

CA $4,932

per person

Dec 5 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Basseterre (SKB)

9.4/10 Exceptional! (152 reviews)

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3 Night Mountain holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

The Villas at Simpson Bay Resort

Pelican Key

CA $1,035

per person

Nov 3 - Nov 6

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

CA $1,418

per person

Nov 12 - Nov 15

found 18 hours ago

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

Ocean view was not quite true

Reviewed on Oct 2, 2026

COCOS Hotel - Adults Only - Caters to Couples - All Inclusive

Save 100% on your flight

CA $3,476

per person

Nov 1 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. John's (ANU)

9.4/10 Exceptional! (857 reviews)

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4 Night Mountain holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

CA $1,329

per person

Nov 7 - Nov 11

found 5 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

CA $1,389

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

Ocean view was not quite true

Reviewed on Oct 2, 2026

Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

CA $1,432

per person

Nov 5 - Nov 9

just found

Roundtrip non-stop flight included

Montreal (YMQ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,000 reviews)

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Mountain Hotels in Lesser Antilles

Montpelier Nevis

Montpelier Estate Charlestown Nevis

3 hours drive from Oyster Bay Marina

Book a stay at this beach hotel in Charlestown. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

Mafolie Hotel

7091 Estate Mafolie St. Thomas

4 hours drive from Oyster Bay Marina

Stay at this hotel in St. Thomas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...

8.8/10 Excellent! (1,001 reviews)

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Reviewed on Sep 30, 2026

Golden Rock Inn

Charlestown Gingerland Nevis

3 hours drive from Oyster Bay Marina

Stay at this hotel in Gingerland. Enjoy free WiFi, room service, and in-room massages. Popular attractions Eva Wilkin Gallery and Market Place are located ...

9.8/10 Exceptional! (37 reviews)

"The Golden Rock is a one of a kind property and we cannot wait to go back. The cleanliness was a 10/10 and the landscaping was absolutely stunning. The restaurant was excellent for every meal we had. I highly recommend the conch chowder. Thank you Golden Rock!"

Reviewed on Mar 26, 2026

See all 15,315 properties in Lesser Antilles

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.