Haute Shopping, Travel | October 8, 2025

Our Haute Guide to a Romantic Weekend Upstate

Haute Shopping, Travel | October 8, 2025

By Gaby Keiderling, E-commerce Director at Haute Living

Photo Credit: Bonnie & Clyde Cottage

Whether you’re planning ahead for Valentine’s Day, celebrating an anniversary, or simply looking for an excuse to sneak away from city life, Upstate New York is one of our favorite destinations to escape to for romance. From its variety of luxury hotels to its charming Airbnbs to its fine dining establishments highlighting local produce, the Hudson Valley and its surrounding area offers intimate serenity just a two-hour-or-less drive from New York City. Instead of inundating you with countless options, we are going to keep it concise.

Here’s how to have the most romantic weekend away.

To Get There

While you can hop on the train, I personally prefer to drive. Audi’s SQ7 Prestige was the perfect car for my trip upstate; it was spacious enough to store all of our bags, and it drove as silently and smoothly as possible. You will most likely want a car Upstate as well, for exploring the nearby towns, orchards, and hiking trails.

To Stay

The Luxury Countryside Hotel: Inness

Photo Credit: Adrian Gaut

Perhaps the most gorgeous hotel I have ever stayed at, Inness is more of a lifestyle than an estate. Of course, it’s that, too. The property boasts 220 acres of scenic terrain, with 28 elegant cabins and the 12-room farmhouse for accommodations.

Photo Credit: Adrian Gaut

While the captivating mountain views and sprawling landscape transcend reality, the actuality of the hotel’s offerings is just as unparalleled. There’s a state-of-the-art 9-hole golf course, hardcourt tennis courts, two saltwater pools, a posh gym and spa, as well as endless hiking and biking trails (and even an obstacle course). Mind-and-body connection is at the forefront of Inness’s ethos, and it’s clear throughout its intentional offerings that make the most of its breathtaking scenery. There’s truly something for everyone at Inness.

Book Inness Now

The Charming Airbnb: Bonnie and Clyde Cottage

Photo Credit: Bonnie & Clyde Cottage

If you would prefer to go the Airbnb route—or perhaps just be in a place that feels like a home away from home—this stunning cottage is the perfect choice. This newly renovated cottage brings rustic elegance to life, featuring two cozy bedrooms and naturally-lit living area. You can cook comfortably in the gourmet kitchen and then enjoy your meal on the private deck. Use the fire pit to whip up some smores for dessert.

Photo Credit: Bonnie & Clyde Cottage

Aside from its contemporary amenities, what really sets this Airbnb apart from all of the rest is its interior design. The owner, Danielle James, has her own interior design company called Homecoming, and she brings her company’s thoughtful approach to décor to her cottage. Vintage elements in the bedrooms reflect the quaint cottage history, furthered by decorative nods to the past in the kitchen and living area. The spacious layout has comfort and style at its core, ensuring that guests can unwind in serenity after a day of exploring the nearby vibrant towns of Rosendale and Kingston.

Book Bonnie and Clyde Cottage Now

To Dine

For Breakfast, Bagels: Fantzye Bagels

You might be able to escape the city, but you can’t escape bagel sandwiches. And nor should you want to. Fantyze Bagels makes some of the best I’ve ever had—fresh handmade sourdough bagels topped with local ingredients of your choosing.

A Local Lunch: Little Goat

Photo Credit: Kate Sears

Drive over to Rhinebeck for lunch at this beloved bakery, pantry, and all-day café. It embodies lowkey country chic, with whimsical and playful dishes that spotlight Upstate specialities. Think: tomato panzanella salad, linguini with littleneck clams, and grilled Hudson Valley steelhead trout with green tomatoes and labneh.

Fine Dining with a View: The Restaurant at Inness

Photo Credit: Alexander Stein

Naturally, The Restaurant at Inness lives up to the hype of the hotel itself. Sit outside on the balcony for an alfresco dining experience to feast on bluefin tuna tartare crostinis and tilefish with zucchini tempura set against a backdrop of rolling mountains and grassy expanses.

The Hot Spot in Town: Restaurant Kinsley

Photo Credit: Alexander Stein

Last, but most definitely not least, head into Kingston for a lively dinner at Hotel Kinsley’s eponymous restaurant. Its new executive chef, Spencer Coplan, brings Southern and French influences to the New American cuisine. The modern spot also captures the invigorating essence of the town—through its artistic interiors, carefully crafted cocktails, and locally-sourced menu. Pro tip: order the squash donuts. Trust me on this.