Memorial Day Weekend, But Make It Luxurious: Where to Escape If You Want to Splurge This Summer
Memorial Day Weekend is one of the smartest times of year to take a quick luxury escape, if you do it correctly.
Everyone else is sitting in six hours of traffic trying to get to the same beach town at the same time. Meanwhile, the savviest travelers are boarding a nonstop flight, checking into a beautiful hotel, ordering a cocktail by the pool, and mentally clocking out of spring.
This is your sign to leverage that extra day properly.
If you want to splash out a little this Memorial Day Weekend, these are the types of properties I’d recommend booking through me as your travel advisor — not just for the hotel itself, but for the perks, upgrades, advocacy, and strategy behind how you book.
Because on a busy holiday weekend, how you book matters.
The Memorial Day Rule: Nonstop Flights Only
If there is one holiday weekend where I become militant about nonstop flights, it’s Memorial Day.
This is not the weekend for:
tight layovers
regional connections
“the cheaper option”
adding unnecessary drive time after landing
The goal is simple:
Get out of town quickly and start your summer feeling relaxed, not depleted.
Even if the hotel is a splurge, the nonstop flight is often the real luxury.
And if you can leave Thursday evening instead of Friday afternoon? Even better.
(And if you’re trying to maximize every long weekend this year strategically, make sure to read my PTO 2026 planning guide here)
For Coastal Glamour: Nantucket & New England
White Elephant
Hydrangeas. Harbor views. Champagne at sunset. Cashmere after dinner even in June.
Nantucket is one of those destinations that simply feels like summer. Memorial Day Weekend is especially ideal because the island is lively without the peak-July intensity.
This is the move for travelers who want:
elevated coastal energy
beautiful design
boutique shopping
long lunches and harbor walks
a true East Coast summer aesthetic
You can fly nonstop into Nantucket from several East Coast gateways and completely avoid the ferry-and-traffic chaos. If you want Nantucket & Martha’s Vineyard, check this guide.
Ocean House
One of the grand dames of New England luxury. Yellow Victorian architecture overlooking the Atlantic, croquet lawns, impeccable service, and a true “summering” atmosphere.
This is for travelers who want old-school East Coast elegance with modern luxury service.
Cliff House Maine
For travelers craving quiet luxury instead of scene-y luxury.
Think:
dramatic ocean cliffs
spa days
fireplaces
lobster rolls
cool Maine air
slow mornings with coffee overlooking the Atlantic
A perfect reset after a nonstop spring.
For a Stylish Summer Kickoff: Montauk
Gurney's Montauk Resort & Seawater Spa
Montauk Nights
If you want Memorial Day Weekend to feel like the official launch of summer, this is it.
Beach club energy. Oceanfront rooms. A seawater spa. Sunset cocktails.
Done correctly — meaning early arrival and no driving once you’re there — Montauk can feel incredibly fun and celebratory.
Done incorrectly? You spend your weekend in traffic.
This is exactly where a strategic travel plan matters.
For a Quiet Luxury Escape Instead
Not everyone wants beach crowds for Memorial Day.
Some travelers want:
silence
wellness
mountain air
fireplaces
wine by a lake
zero social obligations
Twin Farms
One of the most exclusive luxury retreats in the United States.
Private cottages, hyper-personalized service, incredible food, and complete privacy. This is the type of place where people go to genuinely exhale.
The Lodge at Primland, Auberge Resorts Collection
An incredible long-weekend option for East Coast travelers wanting nature without sacrificing luxury.
Horseback riding, stargazing, golf, spa treatments, mountain views, and enough space to fully disconnect from daily life.
Why Book Through a Travel Advisor for a Holiday Weekend?
Holiday weekends are exactly when having a travel advisor matters most.
Because when things become crowded or complicated, relationships and booking channels matter.
Booking through an advisor can often include:
complimentary breakfast
hotel credits
room upgrades
preferred placement within the hotel
VIP recognition
flexible support if travel disruptions happen
More importantly, you have someone advocating for your experience before you even arrive.
Luxury today isn’t always about excess. Often, it’s about ease.
The best Memorial Day Weekend trips are the ones where:
the flights are simple
the hotel understands your preferences
the details are handled
and summer starts the moment you leave home
If you’re thinking about a last-minute Memorial Day escape or planning your summer strategically around long weekends, don’t wait to minute longer.
