Build Your Trip

USA Holiday Season Travel

This year, plan a special trip for Thanksgiving or winter break. Whether you're looking for fun in the sun, a theme park adventure, gastronomic delights or thrills on the slopes, we have you covered with great deals in popular destinations across the U.S.

All Holiday Vacations

Hyatt Regency Washington on Capitol Hill

Downtown / Chinatown Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

This upscale hotel in the heart of Washington, D.C. affords easy access to all the attractions in the nation's capital.

Book Now
Walt Disney World Swan

Disney Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

The perfect gateway to Central Florida's theme parks, this resort offers magical surroundings and luxurious amenities.

Book Now
The Ritz-Carlton, Boston

Boston, MA Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

Festive Season Celebration: Usher in the holiday spirit with time-honored traditions including themed brunches with Mrs. Claus, hot cocoa and the Overnight Nutcracker Escape. This year, make magical holiday memories for young and old.

Book Now
New York Marriott Marquis

Times Square Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

This vibrant fixture in the center of Times Square is only minutes from New York's most famous attractions.

Book Now
Bellagio Las Vegas

Las Vegas, Nevada Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

Iconic fountains, luxury rooms, world-class dining, fine art, and an elegant casino experience make Bellagio a timeless Las Vegas destination.

Book Now

Park Hyatt Aviara Resort, Golf Club & Spa: Offer valid on new bookings for select 2022 travel. 4th night FREE and $100 resort credit with minimum 4-night stay. Resort credit is not redeemable for cash, non-transferable and must be used during the length of stay.

Hyatt Regency Washington on Capitol Hill: $23 plus tax for a third night stay offer valid on new bookings made by 12/01/22 for select travel through 12/01/23. Three-night minimum stay required. A limited number of rooms are allocated to this offer. No refunds or any unused portion of the offer. Offer is not valid with groups/conventions and may not be combined with other promotional offers. Promotional blackout periods may apply.

Walt Disney World Swan: Up to 35% OFF room rates valid on new bookings made by 11/20/22. Discount varies based on travel dates, length of stay and room category booked. Certain restrictions may apply

Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]