
Lesser Antilles Mountain Vacations
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Flight and Mountain hotel deals in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa
Pelican Key
CA $1,099
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
The staff were amazing, food was great, beach was clean and very easy to access. Our only small issues were that it was not really handicapped friendly, and parking was tight. We had a big van that we rented to hold my dad motorized wheel chair and we had to take up 2 spots each time we parked or we wouldn’t be able to get in the car if someone parked next to us. The curbs did not have handicapped access to get on and off with the motorized wheelchair. It was amazing other wise and we would return in the future.
Reviewed on Aug 16, 2026

The Villas at Simpson Bay Resort
Pelican Key
CA $1,278
per person
Oct 18 - Oct 23
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
We loved the Beach Bar put back. Super friendly. Great food and drinks! The location of the hotel is in a great place. It's close enough to walk to several restaurants and also the supermarket.
Reviewed on Aug 16, 2026


Montpelier Nevis
CA $1,658
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Newcastle (NEV)
9.8/10 Exceptional! (173 reviews)
I’ve travelled all across the Caribbean and the Montpellier hotel is by far the best I’ve stayed at. That is mostly due to the staff who are so friendly and catered to our every need within the hotel, and ensuring all our excursions from the hotel ran smoothly.
I hope to return to Montpellier soon.
Reviewed on Aug 8, 2026

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View all trips5* Mountain holidays in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.

Four Seasons Resort - Nevis
CA $3,609
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Basseterre (SKB)
9.4/10 Exceptional! (149 reviews)
The staff at the Four Seasons were amazing including the bellman, the housekeeper, the breakfast wait staff, the guest services manager and food & beverage manager, the golf pro shop staff, the staff at the lunch spot by the pool and the front desk staff. The Soa was excellent. Birthday celebrations for me and my husband were fantastic, including dinner on the beach. The room was great and spacious. We had a spectacular ocean view room with a balcony. We felt very special by everyone at the resort. I highly recommend the Four Seasons Resort. We had some dinners in property and others off property which was a nice mix. The staff at the resort were very helpful to book dinner reservations and taxis for us in advance.
Reviewed on Aug 16, 2026
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See all available trips from Columbus to Lesser Antilles
View all trips3 Night Mountain holidays in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa
Pelican Key
CA $762
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
The staff were amazing, food was great, beach was clean and very easy to access. Our only small issues were that it was not really handicapped friendly, and parking was tight. We had a big van that we rented to hold my dad motorized wheel chair and we had to take up 2 spots each time we parked or we wouldn’t be able to get in the car if someone parked next to us. The curbs did not have handicapped access to get on and off with the motorized wheelchair. It was amazing other wise and we would return in the future.
Reviewed on Aug 16, 2026

The Villas at Simpson Bay Resort
Pelican Key
CA $907
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
We loved the Beach Bar put back. Super friendly. Great food and drinks! The location of the hotel is in a great place. It's close enough to walk to several restaurants and also the supermarket.
Reviewed on Aug 16, 2026

Don't see what you're looking for?
See all available trips from Columbus to Lesser Antilles
View all trips4 Night Mountain holidays in Lesser Antilles
Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa
Pelican Key
CA $853
per person
Oct 29 - Nov 2
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (1,922 reviews)
The staff were amazing, food was great, beach was clean and very easy to access. Our only small issues were that it was not really handicapped friendly, and parking was tight. We had a big van that we rented to hold my dad motorized wheel chair and we had to take up 2 spots each time we parked or we wouldn’t be able to get in the car if someone parked next to us. The curbs did not have handicapped access to get on and off with the motorized wheelchair. It was amazing other wise and we would return in the future.
Reviewed on Aug 16, 2026

The Villas at Simpson Bay Resort
Pelican Key
CA $1,061
per person
Oct 22 - Oct 26
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,484 reviews)
We loved the Beach Bar put back. Super friendly. Great food and drinks! The location of the hotel is in a great place. It's close enough to walk to several restaurants and also the supermarket.
Reviewed on Aug 16, 2026

Princess Heights Luxury Boutique Condo Hotel
Oyster Pond
CA $934
per person
Oct 22 - Oct 26
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,003 reviews)
The property was beautiful, clean and the staff was impeccable! They put a bottle of wine in my room on my birthday. The front desk was amazing and also the housekeepers.
Reviewed on Aug 13, 2026
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See all available trips from Columbus to Lesser Antilles
View all tripsMountain 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 ...
9.8/10 Exceptional! (174 reviews)
"I’ve travelled all across the Caribbean and the Montpellier hotel is by far the best I’ve stayed at. That is mostly due to the staff who are so friendly and catered to our every need within the hotel, and ensuring all our excursions from the hotel ran smoothly. I hope to return to Montpellier ..."
Reviewed on Aug 8, 2026

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 ...

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
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.
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