The Settlement Vacation Packages 2026 from $2,157

The Settlement flight + hotel vacation packages

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

Nanny Cay Resort and Marina

$2,157

per person

Jan 24 - Jan 31

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Tortola (EIS)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

The Aerial, BVI

Save 100% on your flight

$7,204

per person

Jan 24 - Jan 31

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.

Bitter End Yacht Club

Save 100% on your flight

$6,724

per person

Feb 14 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Tortola (EIS)

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.

Scrub Island Resort, Spa & Marina

Save 100% on your flight

$2,350

per person

Feb 14 - Feb 19

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Tortola (EIS)

This luxury hotel 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.

Saba Rock Resort

Save 100% on your flight

$6,001

per person

Mar 8 - Mar 14

found 24 hours 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.

Top The Settlement hotels deals

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

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

Saba Rock Resort

North Sound Saba Rock

$579 nightly

$632 total

Jan 15 - Jan 16, 2026

Total with taxes and fees

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

Mango Bay Resort

Plum Bay Road, The Valley Virgin Gorda Virgin Gorda

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An outdoor pool is featured at this apartment, along with concierge services and barbecue grills. Enjoy a day at the beach snorkeling, or relax with beach umbrellas.

Pool

Air conditioning

VERY Private, Spectacular, Waterfront Location

Virgin Gorda British Virgin Islands

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This villa includes a garden and barbecue grills.

Pool

Kitchen

Bitter End Yacht Club

North Sound Road Virgin Gorda

$2,008 nightly

$2,191 total

Dec 22 - Dec 23

Total with taxes and fees

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.

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 $2,157, 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.