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$49·Westgate Events·3N/4D·Three-night stay at …$49·GoVIP·3N/4D·Three-night stay at …$59·Westgate·3N/4D·30,000+ sq ft Sports…$59·Westgate·2N/3D·2 Wild Bear Falls Ti…$59·Westgate·2N/3D·Luxury Studio Suite $59·VacationVIP·3N/4D·4 Days / 3 Nights$59·Westgate·3N/4D·Oceanfront resort cl…$59·Westgate·3N/4D·Travel between 1/2 -…$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·Westgate·3N/4D·Resort close to Silv…$59·VacationVIP·3N/4D·4 Days / 3 Nights$59·Westgate·3N/4D·Bonus! $50 Gift Card$79·Westgate Events·2N/3D·2 nights at Westgate…$79·Westgate·2N/3D·Near Great Smoky Mou…$79·Westgate·2N/3D·Top Orlando Deal!$79·Westgate·2N/3D·30,000+ sq ft Sports…$79·Westgate Events·3N/4D·3 nights at Westgate…$79·Westgate·2N/3D·Spacious Accommodati…$79·Westgate·3N/4D·4 days / 3 nights

Vacation Deals in Maui in Winter

5 winter vacation deals in Maui, from $150.

Winter vacpacks in Maui split into two categories: warm-weather escape or snow destination. 5 packages are valid for winter stays right now from \$150.

Hawaii's Maui market is small but high-value. HGV and Marriott Vacation Club both operate preview programs on Ka'anapali, with beachfront suites, whale-watching seasons, and 50,000+ Hilton Honors point bonuses bundled in.

January-February are typically the cheapest months for Maui vacpacks. December holiday weeks and ski-season weeks at mountain resorts carry premiums; late-January dips are often the lowest-price weeks of the year.

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Showing 5 deals in Maui in Winter

Peaks & Pacific Bundle - 37 Days / 31 Nights

31 Nights / 37 Days

$150$3545
Includes trips to: Maui, Hawaii, Maui, Hawaii, Portland, Oregon, Portland, Oregon, Monster Week Trip, White Glove Service, Share This Destination Via Email, Share This Promotion Via Email8 Day Open Destination TripWhite Glove Service- 5 Days & 4 nights- Many resort options- 5 Days & 4 nights- Many resort optionsWrapped in your bundle is our White Glove Service! This program provides the ability to reschedule your first booked trip without incurring any fees. With our White Glove Service, you will immediately be bumped up to our VIP priority status!Sign up now to download your free eBook and receive unbeatable deals straight to your inbox. Your adventure starts today!Sign up now to download your free eBook and receive unbeatable deals straight to your inbox. Your adventure starts today!Ultimate Flexibility: Reschedule your trip once anytime up to the day of arrival with no fees.Bonus Getaway: A 6 day, 5 night all-inclusive vacation to unwind again.A 5 Day / 4 Night All-Inclusive International TripAn 8 Day / 7 Night Monster Week Trip To One Of Our 1,000+ DestinationsAll-inclusive resort with meals, drinks & alcoholBonus Monster Week trip (8 days/7 nights to select destinations)
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Island Hopper Bundle - 38 Days / 32 Nights

32 Nights / 38 Days

$150$4212
Includes trips to: Maui, Hawaii, Maui, Hawaii, Puerto Plata, Puerto Plata, Dominican Republic, Puerto Plata, Dominican Republic, Monster Week Trip, White Glove Service, Share This Destination Via Email, Share This Promotion Via Email8 Day Open Destination TripWhite Glove Service- 5 Days & 4 nights- Many resort options- 6 Days & 5 nights- All-inclusive resort- Meals, drinks & alcohol included- Private, furnished balcony or terrace- Trip covers 2 adults & 2 children under 13- Non-motorized water sports includedWrapped in your bundle is our White Glove Service! This program provides the ability to reschedule your first booked trip without incurring any fees. With our White Glove Service, you will immediately be bumped up to our VIP priority status!Sign up now to download your free eBook and receive unbeatable deals straight to your inbox. Your adventure starts today!Sign up now to download your free eBook and receive unbeatable deals straight to your inbox. Your adventure starts today!Ultimate Flexibility: Reschedule your trip once anytime up to the day of arrival with no fees.Bonus Getaway: A 6 day, 5 night all-inclusive vacation to unwind again.A 5 Day / 4 Night All-Inclusive International TripAn 8 Day / 7 Night Monster Week Trip To One Of Our 1,000+ DestinationsAll-inclusive resort with meals, drinks & alcoholBonus Monster Week trip (8 days/7 nights to select destinations)
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Resorts At this destination, Kahana Beach Resort

4 Nights / 5 Days

$297
Beachfront locationOutdoor swimming poolSun deck / lounge areaFree Wi-Fi in public areasParking (extra charge for all)Our packages cover 4-6 people, depending on the destination. Our Branson, Orlando, and Myrtle Beach packages all cover up to 6, with the rest of our destinations covering 4.We are located in Myrtle Beach, SC!Bonus Getaway: A 6 day, 5 night all-inclusive vacation to unwind again.A 5 Day / 4 Night All-Inclusive International TripAccommodations for up to 6 guests
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The Westin Nanea Ocean Villas

5 Nights / 6 Days

$499
6 Days / 5 Nights villa accommodationMarriott Bonvoy Points bonusFull kitchen suiteWestin Heavenly BedResort amenities & pool accessUp to 12 months to travel
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Hyatt Vacation Club at Ka'anapali Beach

3 Nights / 4 Days

$999
4 Days / 3 Nights accommodations$50 Resort Certificate or 5,000 World of Hyatt PointsBeachfront resort amenitiesUp to 12 months to travel
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FAQs about Maui in Winter

Frequently Asked Questions

Is January a good month for vacpacks?

Yes — for beach and theme-park destinations, January-early February are often the cheapest weeks of the year.

Are ski vacpacks a thing?

Yes. Park City and Lake Tahoe run ski-in/ski-out preview stays with lift-ticket bundles, typically $299-$499 for 3-4 nights.

Is there a deposit required?

Yes — most vacpacks require a $49-$199 refundable deposit at booking, which is returned after you attend the 90-minute presentation. It's not an extra charge; it's a no-show deterrent.

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