The Settlement Vacations 2026 from CA $2,371

The Settlement flight + hotel packages

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

Coconut Tree Villa

CA $2,371

per person

Apr 23 - Apr 29

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Tortola (EIS)

Stay at this hotel in East End. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Tortola Cruise Ship Port and Little Bay are located nearby.

Sugar Mill hotel

CA $2,638

per person

Apr 23 - Apr 30

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Tortola (EIS)

Book a stay at this beach hotel in West End. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Tortola Cruise Ship Port and North Shore Shell Museum are located nearby.

Bitter End Yacht Club

CA $8,131

per person

Apr 12 - Apr 18

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Tortola (EIS)

Book a stay at this beach hotel in Virgin Gorda. Enjoy 2 restaurants, a beach locale, and a marina. Popular attractions Bitter End Gardens and Prickly Pear National Park are located nearby.

Scrub Island Resort, Spa & Marina

CA $3,402

per person

Apr 12 - Apr 18

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Tortola (EIS)

Book a stay at this luxury hotel in Scrub Island. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Marina Cay Beach and Cam Bay Beach are located nearby.

Cane Garden Bay Beach Hotel

CA $3,848

per person

Apr 12 - Apr 18

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Tortola (EIS)

Book a stay at this beach hotel in Cane Garden Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Tortola Cruise Ship Port and Cane Garden Bay Beach are located nearby.

Top The Settlement hotels deals

Four Diamonds Park Villas

Anegada The Settlement Anegada

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Book a stay at this beach villa in The Settlement. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Flamingo Pond Lookout and Loblolly Bay Beach are located nearby.

Pool

Kitchen

Sea Grape Villas

The Settlement The Settlement Anegada Island

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Stay at this villa in The Settlement. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Loblolly Bay Beach and Loblolly Bay are located nearby.

Kitchen

Washer

Saba Rock Resort

North Sound Saba Rock

Free cancellation

Reserve now, pay when you stay

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Stay at this resort in Saba Rock. Enjoy free WiFi, 2 restaurants, and a marina. Popular attractions Bitter End Gardens and Prickly Pear National Park are located nearby.

Spa

Free WiFi

Mango Bay Resort

Plum Bay Road, The Valley Virgin Gorda Virgin Gorda

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Book a stay at this beach apartment in Virgin Gorda. Enjoy a beach locale, onsite spa services, and daily housekeeping. Popular attractions Mahoe Bay Beach and Mahoe Bay are located nearby.

Pool

Air conditioning

Oil Nut Bay

Oil Nut Bay Virgin Gorda

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Book a stay at this beach resort in Virgin Gorda. Enjoy free WiFi, free parking, and 4 outdoor pools. Popular attractions Oil Nut Bay Beach and Bitter End Gardens are located nearby.

Leverick Bay Resort and Marina

North Sound Virgin Gorda Virgin Gorda Virgin Gorda

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Book a stay at this spa hotel in Virgin Gorda. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Leverick Bay Marina and Leverick Bay are located nearby.

Pool

Spa

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See all available properties in The Settlement

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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.

Popular places to visit

Loblolly Bay Beach

Why not spend a carefree afternoon at Loblolly Bay Beach during your travels in The Settlement? While you're in the area, stroll along the seaside.

Loblolly Bay

Commune with nature and explore the great outdoors at Loblolly Bay during your travels in The Settlement. Wander the beaches and seaside while you're in the area.

Frequently asked questions

How much are vacation packages to The Settlement?

Starting from as little as CA $2,371, hotel and flight packages are a great way to stretch your travel budget. Get ready The Settlement — here you come!

Where can I get the best vacation package deals for The Settlement?

Book your dream vacation with Travelocity. With access to 400 airlines and 1,000,000 properties across the globe, selecting the ultimate The Settlement package deal couldn't be easier.

Why should I book my The Settlement vacation package via Travelocity?

We take the stress out of travel planning. Whether you're searching for a new destination to uncover or want to make sure you get the best price on offer, we've got your back. Our 24/7 customer care, high-quality service and Price Match Guarantee mean you can book with confidence.

Will I save money on my The Settlement car rental if I bundle it with a hotel or flight?

You certainly can with our The Settlement vacation packages. With one of these, there are plenty of ways to make your travel budget go further. Combine any two or more car, hotel, flight and tour bookings and watch your savings pile up. With a rental car, all the attractions in and around The Settlement are a fun road trip away.