Last Minute Labor Day Deals I'm Sending Clients Right Now 🤍
Labor Day weekend is one of the best times to travel — hello, extra time off!
and if you've been on the fence about a late summer trip, consider this your sign.
I have been prepping proposal and checking availability for clients at some of my absolute favorite properties and figured you may need to see this..
These are for September 2–7 (5 nights, double occupancy), and every single one of these includes preferred partner perks + Benefits!
Here's what I've got:
DOMESTIC ESCAPES
Keswick Hall — Charlottesville, Virginia | ~$6,800 A stunning Virginia estate that feels like you've been transported to the English countryside — except you're a wine country drive away from home. beautiful rooms, world-class golf, a breath taking infinity pool, and a farm-to-table dining experience that will blow you away. Perfect for a romantic late summer escape.
Terrenea Resort — Rancho Palos Verdes, California | ~$5,950 Perched on the Southern California coastline with sweeping Pacific views, Terrenea is one of those properties that makes you feel like you've found a secret. we’re talking coastal spa days, incredible seafood, and the kind of sunset that makes you never want to leave.
Four Seasons Vail — Vail, Colorado | ~$4,414 late summer in a ski town — one of my favorite travel experiences. and this might be one of the most underrated travel moments — golden aspens, zero crowds, and crisp mountain air. The Four Seasons here is exceptional, and the rates this time of year make it an incredible value for this level of luxury.
One & Only Moonlight Basin — Big Sky, Montana | ~$11,400 This one has been wow-ing clients all summer and i cannot believe it has availability. do not sleep on this. Moonlight Basin is one of the most dramatic, remote, and jaw-dropping properties in the country. This is a bucket list trip, and September is arguably the most beautiful time to be in Montana.
Paws Up — Montana | ~$17,000 (All-Inclusive) Same story — availability at Paws Up in September is basically a unicorn. This is a fully all-inclusive luxury glamping and ranch experience in the Montana wilderness, and it's unlike anything else. The all-inclusive price tag means food, activities, and experiences are all wrapped in. Worth every single penny.
Hidden Pond — Kennebunkport, Maine | ~$6,800 If a cozy, tucked-away Maine escape is calling your name, Hidden Pond is the answer. September is peak fall-in-Maine magic — crisp air, lobster, beautiful foliage starting to show. This property is intimate, beautifully designed, and endlessly charming.
Nemacolin — Farmington, Pennsylvania | ~$6,475 A one-of-a-kind resort in the Pennsylvania mountains with more to do than most destinations twice its size — think spa, golf, art galleries, off-road adventures, and exceptional dining all on one property. A Labor Day long weekend here feels like a full vacation.
Pendry Natirar — Somerset, New Jersey | ~$7,400 Tucked into 500 acres of New Jersey countryside, Natirar is a true hidden gem for the East Coast crowd. Gorgeous estate grounds, a stunning spa, incredible farm-driven cuisine, and a level of privacy and serenity that's hard to find this close to NYC.
Fairmont Chateau Whistler — Whistler, BC | ~$2,000 Arguably the best value on this entire list. The Fairmont Chateau Whistler in late summer/early fall is absolutely stunning — world-class hiking, mountain biking, and that iconic Whistler village energy, all wrapped in a beautiful property with an unbeatable price right now.
CARIBBEAN + BERMUDA
Jamaica Inn — Ocho Rios, Jamaica | ~$2,500 Classic, elegant, Old World Jamaica at its finest. Jamaica Inn has been a hideaway for artists and romantics for decades, and it shows in every detail — the white-gloved service, the gorgeous oceanfront cottages, the sense that time moves a little slower here. An absolute steal at this price.
Ritz-Carlton Aruba | ~$3,400 Aruba is one of the most consistently sunny, calm, and gorgeous islands in the Caribbean — and the Ritz here delivers on every front. September weather in Aruba is reliably beautiful (it sits below the hurricane belt), so this is a smart play for late summer.
Hamilton Princess — Bermuda | ~$4,300 Bermuda's most iconic property with a gorgeous harbor setting, world-class dining, and that quintessentially British-Caribbean charm that Bermuda does better than anywhere. Pink sand beaches, pastel cottages, and a level of sophistication that makes it feel like a European trip without the transatlantic flight.
Silversands Beach House — Grenada | ~$4,300 Grenada is one of the most underrated islands in the Caribbean — lush, spicy (literally, it's the Spice Isle!), and unspoiled. Silversands is a stunning, ultra-modern property on one of the most beautiful beaches on the island. If you want something a little off the beaten path with serious luxury credentials, this is it.
Sugar Beach — St. Lucia | ~$7,850 Set in a UNESCO World Heritage valley between the iconic Piton mountains with the most dramatic views in the entire Caribbean. Sugar Beach is the kind of place that photos simply cannot do justice — you have to be there. The setting alone makes it worth it.
Mandarin Oriental Canouan — St. Vincent & the Grenadines | ~$7,500 Canouan is one of the most exclusive, under-the-radar destinations in the entire Caribbean. The Mandarin Oriental here sits on a private island with pristine beaches, a Tom Weiskopf golf course, and that legendary MO service. If you want to feel like you've truly escaped — this is it.
MEXICO
Four Seasons Los Cabos at Costa Palmas (Cabo del Sol) — Los Cabos | ~$4,900 September is shoulder season in Cabo, and the Four Seasons delivers incredible value right now. Swimmable beach (a must!), the most beautiful pool situation, and Four Seasons service at a price point that's genuinely hard to beat for this property.
One & Only Palmilla — Los Cabos | ~$5,640 Palmilla is Cabo royalty. Iconic, stunning, with one of the best beaches on the entire corridor and a sense of timeless elegance that newer properties just can't replicate. If you've been wanting to experience Palmilla, Labor Day weekend availability is your window.
All rates are approximate and based on 5 nights / double occupancy for September 2–7. All bookings include preferred partner perks — complimentary breakfast daily, hotel credits, and room upgrades based on availability.
These won't last — reach out today and I'll hold the room while we sort out details! 🤍
