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These Drivable Getaways Are 4 Hours or Less From Westchester

by Staff
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Featured photo by Oliver Parini

Whether you’re searching for a long weekend escape or a substantial time away, these drivable destinations are doable in four hours max (but you should still bring snacks in case of traffic).

By Carolyn Ann De Melo, Ryan Noel, Kate Schlientz, John Bruno Turiano, Abbe Wichman, and Maya Workowski
Edited by Cristiana Caruso

It’s a routine we tend to fall into: finding a place to take a vacation, realizing it’s kind of far, booking a flight, and being miserable on the travel days (bonus points for each screaming child). Don’t let the airport drudgery capture you yet again. These hideaways meet happily in the middle: local enough to drive to but far enough that you feel like you’re truly vacationing.

Hill Farm by Sagra

Sunderland, VT

Three hours and fifteen minutes from Sleepy Hollow

A visit to this historic bed-and-breakfast is as serene as the picturesque views that border the property. Hill Farm by Sagra (sagrafarms.com/farm-retreats) offers a sustainable stay and cuisine that highlight the surrounding region, all nestled within Vermont’s Equinox Mountain Valley. The inn’s framework has stood for over 200 years — although not always as a B&B — celebrating that the property has lived many lives.

Occupied by a girl-gang of alpacas (Tina, Brittany Spears, Noel, and Miss Latte, respectively) the lush, rolling landscape of Hill Farm by Sagra will settle your soul and put you back in tune with nature (and wine, naturally).
Occupied by a girl-gang of alpacas (Tina, Brittany Spears, Noel, and Miss Latte, respectively) the lush, rolling landscape of Hill Farm by Sagra will settle your soul and put you back in tune with nature (and wine, naturally). Photo by Oliver Parini

The historic, renovated inn has 11 rooms, which feature locally sourced artisan materials. In addition, four quaint cottages sit on the property. Guests are welcome to relax in the shared spaces scattered throughout the main building, equipped with fireplaces, a pool table, and a swimming pool. Property tours are given by the knowledgeable and enthusiastic staff, who dive into the inn’s rich history, and vegetable farm that plays a major role in providing the inn with its vital produce. For animal lovers, the tour concludes with a stop at the alpaca den to feed the inn’s beloved mascots.

getaway experience
Photo by Oliver Parini

You can also savor the taste and tales of Vermont wines with a specialty wine tasting curated by the Hill Farm staff. During the warmer seasons, you can explore the surrounding area and its breathtaking foliage by hiking along the Appalachian trail, fly-fishing on the Battenkill River, or soaking in the mountain views while lounging on the wraparound porch. Its versatility allows for a little slice of heaven for every guest.

getaway
Photo by Oliver Parini

The inn’s culinary experience is arguably the star of the show. For breakfast, made by innkeeper Maria Jones, guests can pick from Hill Farm egg omelets, Earth Sky Time pastries, and other local goodies accompanied with coffee and tea. As the evening rolls in, enjoy seasonal fare at the Grange, the inn’s on-site restaurant. Chef Austin Poulin, previously of Blue Hill at Stone Barns, takes your taste buds on a culinary journey as you eat your way through the locally curated menu. Enjoy a celebration of regional fare within the expansive, wood-framed dining room sprinkled with minimalistic decor.

chef experience
Photo by Oliver Parini

Making a reservation at the chef’s table — where you can watch the talented chefs craft each dish — during your stay is a must. Not to mention, the menu of exquisite sips pair superbly with the dishes. For smaller bites throughout the day, the inn’s farm stand is open daily and is stocked with local charcuterie and treats.

A gourmet farm-to-table experience awaits at Hill Farm, expertly prepared by a Blue Hill alum using local ingredients.
A gourmet farm-to-table experience awaits at Hill Farm, expertly prepared by a Blue Hill alum using local ingredients. Photo by Oliver Parini

Whether it’s the tranquil views, seasonal fare, or generous list of accommodations, there’s no doubt that Hill Farm is an ideal destination for a cozy retreat during any season. Plus, the property boasts the ultimate wedding package for any couple. Rates from $189/night. —Ryan Noel

The Hermitage Inn

West Dover, VT

Three hours and ten minutes from Lewisboro

Skiing and Vermont are an obvious match and the reason why many vacation there, but the Green Mountain State has more to offer than just hitting the slopes on a thick, fresh powder.

The inn is at the base of Haystack Mountain, which means a front-row seat for leaf-peeping
The inn is at the base of Haystack Mountain, which means a front-row seat for leaf-peeping. Photo courtesy of The Hermitage Inn

It is a four-season destination (except April/the bulk of May, aka “mud season,” when the customary four feet of winter snow melts and melts… and melts), and the Hermitage Inn (thehermitageinnvermont.com), a 14-room contemporary resort located in the foothills of Green Mountains, affords an array of seasonal experiences while exemplifying the state vibe: historic, restorative, rural, connected to the land.

A Carriage House suite.
A Carriage House suite. Photo courtesy of The Hermitage Inn

Below Haystack Mountain, across a timber-framed, covered bridge (perhaps the iconic Vermont structure) and over Cold Brook stream is 112 acres of southern Vermont at its most graceful and hospitable. The property’s Historic Inn and Coldbrook rooms offer snug farmhouse comfort and views of the stream while a four-King Suite private carriage house has double vanity sinks, walk-in showers, and jetted tubs. (Frette linens, bathrobes, velour slippers, and Nespresso Vertuo coffee makers are featured in all rooms.)

Reserve one of the heated gondolas for a secluded meal.
Reserve one of the heated gondolas for a secluded meal. Photo courtesy of The Hermitage Inn

Activities on-property include spa services, archery lessons (summer only), ice skating, snowshoeing, exploring valley trails on Aventon Aventure E-Bikes, and fly-fishing at the trout pond. Also, shuttle service is offered to Mount Snow (an 8-minute drive) or one of three lakes for kayaking or SUP.

Built in 1790, the Hermitage was a working farm until the early 1960s, when it became a lodge/restaurant that earned Wine Spectator Grand Awards before closing in 2018 and being dormant for three years; native Vermonters Mary Lou Ricci and Tim Hall bought the Inn in April 2021 and committed to restoring it and its grounds to its former glory.

A firepit gathering during sunset
A firepit gathering during sunset. Photo courtesy of The Hermitage Inn

“It was very important to me to pay homage to the history of the Inn,” says Ricci. “The uses of dark gray and green are historical colors. I also wanted to bring the natural surroundings inside so that every guest has a view of the beautiful surroundings.”

The two restaurants on-site — the less formal, a la carte Tavern and the swanky Birches, featuring a multicourse tasting menu — are run by Consulting Chef Michael Schlow and Executive Chef MacGregor Mann, respectively. The Modern American locavore fare and international wine list (with 400 offerings, the inn was granted a Wine Spectator 2022 Award of Excellence) would position organically into any big-city dining scene.

A maple-syrup stand is within a five-minute drive of the inn
A maple-syrup stand is within a five-minute drive of the inn. Photo courtesy of The Hermitage Inn

It would be an oversight to miss a dose of small-town-New England life by not venturing to nearby (an 8-minute drive) Wilmington. It epitomizes a stroll-worthy Vermont town.

Many a stellar meal can be had in the Birches’ dining room
Many a stellar meal can be had in the Birches’ dining room. Photo courtesy of The Hermitage Inn

Whether it’s leaf-peeping, mountain vistas, any-season outdoor rec, first-class dining, or homey, fireside evenings you long for, The Hermitage provides a classic, and classy, Vermont sojourn. Rates from $300/night. —John Bruno Turiano

W Philadelphia

Philadelphia, PA

Two hours and fifteen minutes from New Rochelle

For a chic, stylish, and luxe vacay in the City of Brotherly love, The W Philadelphia (marriott.com/en-us/hotels/phlwh-w-philadelphia/overview) will cater to every whim — and then some. While you have likely sought out Philly to explore and bask in the history, W offers so many unmatched amenities that you could easily spend all your time on-site. The rooms provide a singular experience, with rotating beds and DJ set-ups (no, seriously). With dark, glamorous aesthetics and a beautiful “living room” area that greets you upon arrival, it’s hard not to see the allure.

The rooftop pool should have a space on everyone’s Philly bucket list, and for good reason: You get an up-close view of Philly’s skyline, surrounded by greenery and an indoor-outdoor bar.
Photo courtesy of W Philadelphia

The rooftop pool should have a space on everyone’s Philly bucket list, and for good reason: You get an up-close view of Philly’s skyline, surrounded by greenery and an indoor-outdoor bar.

The trademark of every W Hotel is the intention with which it infuses the history of the cities within the architecture of their buildings. For Philadelphia, this means abstract art mirroring the walkable grid layout of the city and cheeky quilt patterns featuring shirtless, muscled Ben Franklins. It’s this spark in everything done at W that sets it a cut above other hotel options in the city.

outdoor area
Photo courtesy of W Philadelphia
beautiful bedroom getaway
Photo courtesy of W Philadelphia

Beyond the undeniable beauty, W has put much intention into creating a functional space. It’s rooftop pool should have a space on everyone’s Philly bucket list, and for good reason: You get an up-close view of Philly’s skyline, surrounded by greenery and an indoor-outdoor bar. The pool is heated, making it ideal for year-round use. After swimming some laps (or lounging, cocktail in hand), you might want to grab some food, and for that you have Dolce: W’s Italian restaurant on the first floor. If you’re not looking to get your buzz on, Dolce offers zero-proof cocktails; while it’s a hard feat to find mocktails that don’t rely on club soda, the Cosmos at Dolce are the real deal.

Bejeweled with luxurious amenities and sky-high views, The W Philadelphia provides an unforgettable stay in the City of Brotherly Love.
Bejeweled with luxurious amenities and sky-high views, The W Philadelphia provides an unforgettable stay in the City of Brotherly Love. Photo courtesy of W Philadelphia

For the workout nuts, spend your time working up a sweat at the weekly rooftop Pilates sessions and then rejuvenate with a tranquility-centered facial at Away Spa, W’s in-house spa. Hours could slip away post-session in the red-velvet relaxation room, complete with a stocked tea station, magazines, and plush, heavyweight robes. It’s optional (but highly recommended) to put your phone away and just soak up the good vibes — because W is more than a hotel. It’s a community of amazing people waiting to call you a friend.

Philadelphia inn
Photo courtesy of W Philadelphia

And you may be wondering: What does “W” stand for anyway? It is safe to say, and after one night you’ll agree: Wonderful. Rates from $322/night. — Maya Workowski

The Lenox Collection

Lenox, MA

Two hours and twenty minutes from Dobbs Ferry

Nestled in the historic town of Lenox, travelers will find a respite at The Lenox Collection (thewhitlocklenox.com), a trio of small, historic inns, each with its own charm and personality.

Steeped in class and history, The Lenox Collection offers guests and visitors a delightful detour from some of the more garish flourishes of the modern world.
Steeped in class and history, The Lenox Collection offers guests and visitors a delightful detour from some of the more garish flourishes of the modern world. Photo courtesy of the Whitlock

The inns — The Constance, The Dewey, and Whitlock — had been operating as independent properties before being placed under the umbrella of The Lenox Collection in 2021. All three are walking distance to town, with The Whitlock being in the “center” of the action and the other two slightly on the outskirts. Whether visiting for a romantic getaway or a family reunion, each of the inns offers lodging options that hew to its Colonial roots while offering more modern comforts — think elegance without fussiness.

inn dining
Photo courtesy of the Whitlock

Four-poster beds and classic wallpaper keep with the inns’ historic nature, while plush bedding and renovated bathrooms offer more modern conveniences.

For those whose ideal breakfast or sunset watch involves sitting on a wraparound porch, taking in the views, The Constance is the place to be. The 24-room inn acts as the central check-in location for all three properties, and guests will find a convivial innkeeper there with great area suggestions. There’s a charming breakfast room (if the weather isn’t conducive to that wraparound porch), where guests find a continental breakfast every morning. There’s also a lounge area with board games and a piano.

The Dewey’s presence makes itself known from the street, with its grand façade. The smallest of the inns, The Dewey has nine rooms in the main property and three in a carriage house. Elegant antique furnishings bring character to The Dewey — also antique (but not of Colonial heritage) is a working pay phone tucked away on the main level. The Dewey features a light-filled breakfast area and a magnificent library, also with a piano. With its inviting window seats, you may not want to explore the town.

The Whitlock, in the center of town, is the most modern of the three properties. The 30-room inn features an enclosed porch, an outdoor area with a firepit, and is home to a welcome addition to the Berkshires dining scene, Max. Not owned by the property, the restaurant offers not-to-be-missed Italian food in a setting that befits the inn.

Rooms at all three inns are elegantly appointed. Four-poster beds and classic wallpaper keep with the inns’ historic nature, while plush bedding and renovated bathrooms offer more modern conveniences.

Whether guests visit in the winter, when they’ll be able to enjoy warmth from fireplaces, or during summer months, when they can be warmed by the sun both indoors and outdoors, The Lenox Collection’s three inns provide a sense of history and comfort. Rates from $443/night. —Abbe Wichman

Winvian Farm

Litchfield Hill, CT

Two hours from Yonkers

Nestled in the Litchfield Hills of Connecticut, Winvian Farm (winvian.com) is 113-acres of rolling hills and serene beauty, making it the perfect escape for a tranquil getaway. With 18 themed resort cottages to choose from — think less theme park and more designer-driven dwellings — each offers its own personality and charm. The Artist Cottage is a charming arts-and-crafts bungalow filled with stained-glass windows casting dancing colors throughout. The Greenhouse is one of the more modern lodges — crisp, whitewashed, and giving off those summer-in-New England vibes, even in the coldest of seasons.

With cottages spanning themes including golf, maritime, music, and log cabin, Winvian Farms provides a true escape from the madding crowd. Complete with five-diamond cuisine and luxury spa, consider your batteries recharged and your soul full.
With cottages spanning themes including golf, maritime, music, and log cabin, Winvian Farms provides a true escape from the madding crowd. Complete with five-diamond cuisine and luxury spa, consider your batteries recharged and your soul full. Photo by Hunter Webb

Whether you’re looking to unwind in the wood sanctuary of the Beaver Lodge, enjoy the “tavern-esque” barn-like Charter Oak, or feel at home teeing off in the Golf clubhouse, every cottage offers a beautiful solitude, not to mention a king-size bed, fully stocked fireplace, and private patio.

inn fireplace
Photo by Hunter Webb

If you can’t manage to slip into relaxation mode while enjoying the generous bathroom outfitted with both an oversize jetted soaking tub and steam shower, the luxury spa will be sure to do the trick. The quiet sanctuary offers a variety of signature services including massages, facials, and body treatments. Sip a hot cup of tea as you unwind on one of the lounge chairs in the rustic relaxation room, or book a couples’ massage to enjoy a private suite outfitted with a stone fireplace and bottle of bubbly.

hotel living area
Photo by Hunter Webb
inn
Photo by Hunter Webb

Your evening should start at Maggie’s Tavern for a quick craft cocktail before heading upstairs to the Litchfield Hills restaurant, a popular spot for both guests and locals. The five-diamond restaurant, led by Executive Chef Chris Eddy, offers a fresh perspective on farm to table cuisine matched with a wine cellar boasting over 500 labels from 13 countries. While the food and wine will win over everyone at the table, it’s here where you’ll experience a warmth that extends far past the traditional expectations of hospitality. At Winvian, there’s palpable adoration and excitement behind the multicourse menus, which change (almost) daily and feature ingredients grown on-site or from neighboring farms. The team is clearly celebrating seasonality, but they are also thoughtful to recommend the best location to capture the evening’s breathtaking sunset. Rates from $799/night. —Kate Schlientz

Callicoon Hills

Callicoon Center, NY

One hour and forty-five minutes from Peekskill

This expansive, yet surprisingly unassuming and affordable, 23-acre Catskills resort honors its over-a-century-old roots while growing its contemporary offerings. This forest-lined retreat is so perfectly positioned, you could literally drive right past it if you didn’t keep your eyes open for signs. Upon arrival at Callicoon Hills (callicoonhills.com), you’re handed a welcome packet (and offered a complimentary beverage if you arrive in the afternoon) brimming with information about activities in the area — trails, breweries, and outdoor experiences, like the local alpaca farm.

ny inn
Photo courtesy of Callicoon Hills

If glamping is your thing, stay in the new-for-2023 A-frame units, after an invigorating trek up to a charming, wooded area. For a more traditional experience, try the central boarding house, built in the early 1900s, in the Victorian style.

gym
Photo courtesy of Callicoon Hills

If glamping is your thing, stay in the new-for-2023 A-frame units, after an invigorating trek up to a charming, wooded area. For a more traditional experience, try the central boarding house, built in the early 1870s, in the Victorian style, with a few cedar Adirondack chairs on the porch, just asking to be sat in. You could also stay at the iconic pool house, which was added in the 1950s and surrounds a newly renovated king-size pool, or grab a room a short walk up a hill at the Ridge Rooms, which boast the best views — and if you’re lucky spot some of the socialized deer that roam the property. All 65 rooms are spread across one side of the road, but just across the street, Callicoon Hills has a small, whale-shaped lake, but more importantly their event space, a massive, black barn (dating from 1859) featuring hand-hewn beams imported from Indiana with capacity for 250 people. And if that weren’t enough, just a short scenic stroll behind the barn lies a cinematic-quality forest clearing in front of a babbling brook, perfect for weddings.

stay in the woods
Photo courtesy of Callicoon Hills
Whether the move is glamping under the stars or sleeping with full amenities in the historic boarding house, Callicoon Hills ensures that whatever you’re doing, it’s in style.
Whether the move is glamping under the stars or sleeping with full amenities in the historic boarding house, Callicoon Hills ensures that whatever you’re doing, it’s in style. Photo courtesy of Callicoon Hills

General Manager Eli Rasnick is committed to constant improvement, and to that end, the resort has just added two Scandinavian saunas and an indoor-outdoor gym with Peloton bikes and sunny yoga deck. It would be remiss not to mention they also have a built-in restaurant, Conover Club, offering both dinner and brunch, with a seasonally changing menu featuring locally sourced ingredients. Everything there is thoughtfully crafted, reminiscent of classic dishes, but elevated just enough — for example, rabbit Bolognese.

inn dining
Photo courtesy of Callicoon Hills

Curl up at twilight and roast a s’more at their communal firepit with your family (or by yourself — you do you) but take your time to adventure in the area, returning at night to a place that feels like a celebration of everything you love about an upstate getaway. Rates from $169/night; $99 for glamping. —Carolyn Ann De Melo

Related: 6 New England Vacations to Take From Westchester

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