Planning the Perfect Romantic Getaway to Upstate NY

Want to break up the long, dark winter by grabbing your Honey and heading for the hills? Here’s the low-down on what to do and where to stay for a romantic weekend getaway north of NYC this Valentine’s Day or any other winter weekend.

Where to Stay for a Romantic Weekend Getaway in Upstate NY

Where you choose to stay will set the tone of your romantic getaway, so we’re here to help you choose the right place for your special break with your main squeeze.

Modern Retreats

It’s cold and probably snowy. If the notion of cuddling up in a toasty cabin by a roaring fire is your antidote to the winter blues, check out Tamarack House (Beech Lake, PA) and its striking modern design. With walls of glass overlooking the forest, snowfall will give off the feeling of being in your very own romantic snow globe. Neighboring Narrowsburg has a ton to offer in terms of dining and shopping, as the Catskills are easily accessible, making it the ideal weekend escape.

On the other side of the Hudson River is an equally appealing modern escape, Black Ridge Cabin (Narrowsburg), tucked into the woodlands outside of town. Wake up to blissful quiet in this modern house on an old country road that’s full of old New York State charm.

Secluded Spots

If you’re looking for something with small-town vibes and a bit more seclusion (and mountain views), check out Hudson Hill House in the heart of the Hudson Valley. Set on four private acres with treetops and mountain views, this luxurious home has its very own swimming pool where you can swim and sunbathe in privacy.

Cabins with Hot Tubs

If spending time in a jacuzzi under the stars is your thing, there are numerous options. Check out Wildcat Mountain Cabin (Claryville) for a vacation rental finished with classic American styling. There’s lots to do in the surrounding area — check out the many local eateries, take a day trip to Saratoga Springs, or simply relax on the private terrace and soak up the ambiance.

Scott Brook Cabin (Neversink) is set in lovely natural surroundings and offers plenty of privacy. The hot tub is a year-round attraction and WiFi keeps you connected if you don’t want to switch off completely.

For Couples in Search of Adventure

For adventurous couples, we have a few great options that’ll get you off the beaten track while also being close to ski resorts. Perch Lake Farm (Andes) is a stunner of a home set on 300+ (yes, 300) acres. Snuggle up by the fire pit once night falls for a romantic evening to remember. 

Nearby Plattekill Mountain is usually a bit less crowded with just as stunning views, and if you plan ahead the revered Bovina Fermentory and Brushland Eating House are the ideal Valentine’s dinner spot.

Where to Drink & Dine North of New York City

For some couples, dimming the lights, pouring wine, and preparing a meal together is the relaxed setting in which they best reconnect, following a rigorous work week. But for others, stepping out and exploring the local dining and drinking establishments is how they’d like to spend their date night. 

So here we’ve selected a few of our favorite romantic places and best restaurants in town when it’s just the two of you.

Peekamoose Restaurant & Taproom

• Website: https://www.peekamooserestaurant.com/
• Address: 8373 State Route 28, Big Indian, NY 12410
• Opening hours: 4 pm – 9 pm Thursday, Sunday, Monday / 4 pm – 10 pm Friday & Saturday

The chef/owners of Peekamoose Restaurant & Tap Room (Big Indian) bring their weighty NYC restaurant pedigrees north to be closer to the farms that supply them and serve up delicious fare in a buzzing atmosphere (a great place for aprés ski, if you’ve just come off the slopes at Belleayre). Do make reservations.

Club Room at The DeBruce

• Website: https://www.thedebruce.com/
• Address: 982 Debruce Rd, Livingston Manor, NY 12758
• Opening hours: 5 pm – 10 pm Thursday to Monday for drinks (check the website for dining availability)

While the award-winning tasting menu upstairs has hogged the limelight, the roaring fire and the “downstairs tavern” vibe in the Club Room at The DeBruce (Livingston Manor) set the stage for an intimate and tasty meal from their locally sourced menu.

Silvia

• Website: https://www.silviawoodstockny.com/
• Address: 42 Mill Hill Rd, Woodstock, NY 12498
• Opening hours: 5 pm – 9 pm Monday to Thursday / 5 pm – 10 pm Friday / 4.30 pm – 10 pm Sunday

In Woodstock, Silvia wows with an open kitchen and wood-fired grill. The menu is exciting and food fabulous, and you can stroll the town afterward, peeking in the various shop windows. We’re partial to the green velvet banquette for a lovey-dovey vibe.

Brunette Winebar

• Website: https://www.brunettewinebar.com/
• Address: 33 Broadway, Kingston, NY 12401
• Opening hours: 5 pm – 10 pm Thursday and Friday / 2 pm – 10 pm Saturday / 2 pm – 8 pm Sunday

Brunette Winebar, about 20 minutes east in Kingston, is a triumph of meticulous styling in a whitewashed former barbershop, where small café tables mean you’ll be up close and personal, which is what your romantic weekend Upstate is all about.

Romantic Things to Do During Your Winter Getaway

While it might be perfectly tempting to spend your entire trip snuggled up in your rental and eating delicious food, if you do start to get restless, there are plenty of great things to do in the area.

A few of our favorites include:

• Going skiing or snowboarding. There are a number of great places to go skiing in Upstate New York. 
• Visit one of the wineries in the Hudson Valley. While the harvest is over by the time winter rolls around, many stay open for indoor wine tastings.
• Head out on a winter hike. Enjoy the crisp, fresh air and stunning snowy landscapes. A few of our favorite places for a winter hike include Minnewaska State Park Preserve, Ashokan Reservoir, and Clermont State Historic Site. 
• Indulge in a spa treatment. What says romance more than a couples massage? Some of the best wellness places in Upstate New York include Mirbeau Inn and Spa in Rhinebeck, Glo Spa in Woodstock, and the YO1 in Monticello. 
• Uncover the local art scene at a nearby museum or art gallery. There are plenty to choose from in the area but two of our favorites include the Thomas Cole National Historic Site and the Olana State Historic Site. 

The Best Romantic Getaways Are Awaiting You in Upstate New York

Upstate New York has romance running through its veins and is one of the most charming destinations in America. From vast state parks and the dramatic Niagara Falls to expansive wineries offering wine tasting and secluded hiking trails, this corner of the world has it all.

Whether you’re a native New Yorker or you’re coming from afar, you’ll be glad to know that there are dozens of boutique hotels and bed and breakfasts offering comfortable guest rooms. But for a truly special couples getaway to remember, take a look at our vacation rentals. From historic estates to homes with lake views, you’re sure to find your perfect romantic escape with us.