The Settlement Vacation Packages 2026 from $1,007

The Settlement flight + hotel vacation packages

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

Cane Garden Bay Beach Hotel

Save 100% on your flight

$1,007

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Tortola (EIS)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this hotel. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and free perks like continental breakfast and free self parking.

The Aerial, BVI

Save 100% on your flight

$4,438

per person

Nov 18 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Tortola (EIS)

This resort features a private beach, a full-service spa, and a restaurant. Enjoy the outdoor pool and unwind at the bar/lounge and beach bar.

Saba Rock Resort

Save 100% on your flight

$5,963

per person

Nov 18 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Tortola (EIS)

This award-winning resort features a marina and 2 restaurants. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A garden, luggage storage, and laundry facilities are also on offer.

Coconut Tree Villa

$1,850

per person

Nov 18 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Tortola (EIS)

This hotel features a terrace, laundry facilities, and free self parking. A garden, concierge services, and barbecue grills are also on offer.

Scrub Island Resort, Spa & Marina

$2,433

per person

Nov 18 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Tortola (EIS)

This luxury resort features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with free beach cabanas and sun loungers. Enjoy a meal in one of the 5 restaurants and freebies like WiFi in public areas and a roundtrip airport shuttle.

Top The Settlement hotels deals

Sea Grape Villas

The Settlement The Settlement Anegada Island

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This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Kitchen

Washer

Four Diamonds Park Villas

Anegada The Settlement Anegada

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An outdoor pool, free self parking, and laundry facilities are featured at this villa. WiFi in public areas is free. A terrace, a garden, and barbecue grills are also on offer.

Pool

Kitchen

Saba Rock Resort

North Sound Saba Rock

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This award-winning resort features a marina and 2 restaurants. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A garden, luggage storage, and laundry facilities are also on offer.

Spa

Free WiFi

Leverick Bay Resort and Marina

North Sound Virgin Gorda Virgin Gorda Virgin Gorda

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This traditional hotel features a full-service spa, a marina, and 2 restaurants. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. Enjoy the outdoor pool and unwind at the beach bar and poolside bar.

Pool

Spa

Oil Nut Bay

Oil Nut Bay Virgin Gorda

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A marina, 2 restaurants, and 4 outdoor pools are all featured at this resort. There's fun for all ages with a free kid's club and a playground, and in-room childcare is an added bonus. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Pool

Spa

Bitter End Yacht Club

North Sound Road Virgin Gorda

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This smoke-free hotel features a marina and 2 restaurants. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with a free kid's club and kayaking, and babysitting is an added bonus.

Restaurant

Air conditioning

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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.

Stay near popular The Settlement attractions

Loblolly Bay Beach

10.0/10 (2 reviews)

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.

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Frequently asked questions

How much are vacation packages to The Settlement?

Starting from as little as $1,007, 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.