8 Romantic Valentine’s Day Getaways

From romantic retreats to enthralling activities, make the most of your Valentine’s Day this year with these top destinations.

Valentine’s Day falls on a Saturday this year, so take your significant other for a sleepover at one of these nearby romantic retreats. Wine and dine your valentine and then simply drift upstairs. And for those times when the “privacy” sign isn’t hung on your doorknob, we’ve included activities and nearby destinations to explore.


2¼ hours from White Plains

Blantyre’s stately Main House.

This stately country estate on 220 acres of lawns and woodlands offers 21 guest quarters, including eight exquisite bedrooms and suites, many with fireplaces, on the second floor of the baronial Main House. More informal, country-chic accommodations are housed in a Carriage House and cottages.

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V-Day Vibe: Formal but comfortable, posh yet unpretentious.

Cupid’s Celeb Choice: Outdoorsy sorts with deep pockets who clean up well in uber-elegant surroundings, like William and Kate. (Plus, the pair met at university in Scotland, and this property is named after an ancestral Scottish home.)

On-Property Pleasures: A special Snow Concierge arranges all manner of cold-weather pastimes including horse and sleigh rides; ice skating to music beneath soft lights with breaks for hot cocoa; cross-country skiing and snowshoeing; and Ice Picnics and Snow Bar-B-Ques. Chill out in the Potting Shed Spa’s hot tub and enjoy the view from its rounded walls of windows, work out on the fitness machines, then refuel with a complimentary supply of decadent Dove bars. Enjoy tennis and an outdoor pool in the warmer months.

Nearby Diversions: Stroll the quaint little town of Lenox, tour the historically significant Mount, former home of Pulitzer Prize-winning writer Edith Wharton, or catch seasonal outdoor concerts at the famed Tanglewood music festival, summer home of the Boston Symphony Orchestra.

On-Site Wining & Dining: Relax with Champagne and canapés while a pianist plays classical selections and show tunes. Then repair to the candle-lit dining room, resplendent with china, crystal, sterling silver, and fresh flowers, for an extraordinary formal dining experience. Jackets and collared shirts required; ties preferred.
Pricing: Valentine’s Day weekend prices begin at $600 per night with a three-night minimum. Rates include a welcoming half-bottle of Champagne, a fresh fruit and cheese tray, and chocolate-covered strawberries, plus a full breakfast in the conservatory.

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16 Blantyre Rd,
Lenox, MA

Castle Hotel & Spa

15 minutes from White Plains

Perched atop a sweeping drive on 10 serene forested acres, the Castle, which offers 31 guestrooms and suites, boasts all the Gilded Age interior details you could hope for—carved dark-wood staircases, grand leaded-glass windows, and hand-hewn oak beams in the main house. A member of Small Luxury Hotels of the World and Historic Hotels of America, it was named to Condé Nast Traveler’s “Gold List.”

V-Day Vibe: Old-fashioned enchantment.

Cupid’s Celeb Choice: That reality couple who think they’re royalty, Kim Kardashian and Kanye West
On-Property Pleasures: The heavenly, Thai-inspired THANN Sanctuary Spa, with relaxation lounge, whirlpools, and steam rooms; health and fitness center; and outdoor pool in the warmer months.

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The Relaxation Lounge at Castle Hotel & Spa.

Nearby Diversions: Antiquing in Tarrytown; the Union Church of Pocantico Hills and its magnificent Matisse and Chagall stained-glass windows; and seasonal tours of Kykuit, the Rockefeller estate and historical site of the National Trust.

On-Site Wining & Dining: The ultimate special-occasion restaurant, Equus Restaurant was rated “Excellent” by the New York Times last spring and has received numerous professional accolades including Four Diamonds from AAA, the Five-Star Diamond Award from The Academy of Hospitality Sciences, and the Award of Unique Distinction from Wine Enthusiast Magazine.

Pricing: Rooms start at $529. A Valentine’s Day package includes one night’s accommodation, welcome flutes of Champagne, a five-course dinner for two at Equus, and breakfast. Inquire about special spa packages and room upgrades.

400 Benedict Ave,

Delamar Greenwich Harbor

15 minutes from White Plains

This luxury hotel on Greenwich Harbor offers 82 accommodations—including eight suites—laden with classic furnishings, gilt-framed artwork, marble floors, plush rugs, and elegant draperies. It features charming water views, harbor-side gardens, and 600 feet of private dock.

V-Day Vibe: Sophisticated, cosmopolitan elegance

L’Escale Restaurant at Delmar Greenwich Harbor offers romantic fireside dining.

Cupid’s Celeb Choice: Beyoncé and Jay-Z: The pair loves to frolic on private yachts—and they could dock one here—and indulge in world-class designer shopping on nearby Greenwich Avenue.

On-Property Pleasures: Intimate spa, fitness center, inviting library with comfy seating, and—weather permitting—outdoor waterside lounge areas.

Nearby Diversions: Just a stroll away from upscale designer shopping that rivals Rodeo Drive For a culture fix, the Bruce Museum of Arts and Science showcases fine art and natural history.

On-Site Wining & Dining: The utterly romantic L’Escale Restaurant offers Provençal cuisine with a focus on seafood, water vistas, a roaring fireplace, and a lively bar area with Valentine-appropriate lipstick red seating.

Pricing: Room rates start at $259 and include a light continental breakfast in the lounge. A full à la carte breakfast is served in L’Escale for an additional charge. Inquire about any special spa packages; details not available at press time.

500 Steamboat Rd
Greenwich, CT


1 hour from White Plains

Hidden beyond ornate iron gates set high on a hill amid 150 acres of Hudson Valley farmland, the showpiece of this opulent Relais & Château hostelry is a grand, salmon-colored mansion that calls to mind a Tuscan villa. Expect sumptuous interiors, a sweeping marble staircase, and 18 distinctive guest quarters, all with marble bathrooms and heated floors; some also have fireplaces.

V-Day Vibe: Refined, Old-World style. Posh.

Cupid’s Celeb Choice: The planet’s newest “it” couple, George and Amal, who love their own Italian villa—and other discerning one-percenters who value their privacy—would feel right at home here, tucked away from the prying eyes of the paparazzi.

On-Property Pleasures: An opulent spa with a lavish bathhouse offering ancient Hammam or Turkish bath-cleansing rituals; a museum-worthy private collection of Rauschenbergs, Motherwells, and other renowned artists; and in season, an outdoor pool, palatial courtyard, bocce, tennis, and championship croquet course.

The spa at Glenmere offers ancient Hammam or Turkish bath-cleansing rituals.

Nearby Diversions: Storm King Art Center, the 500-acre open-air sculptural museum in New Windsor; Dia:Beacon contemporary art museum in Beacon.

On-Site Wining & Dining: The stylish, candle-lit Supper Room and cozy Frog’s End tavern both have fireplaces perfect for snuggling and serve outstanding, mostly locally sourced cuisine.

Pricing: Deluxe rooms begin at $550; the Penthouse is $1,650. Includes prepared-to-order gourmet breakfast. Two-night minimum required for Valentine’s Day weekend.

639 Pine Hill Rd
Chester, NY

The Opus (formerly The Ritz-Carlton) Westchester

They didn’t call it The Ritz for nothing. Anticipate that your highest expectations will be exceeded at this sophisticated 146-room high-rise with sweeping city views, impeccable service, and luxurious amenities. Oversized guest rooms feature marble baths and dark-wood cabinets.

V-Day Vibe: Uptown glamour with a touch of downtown chic.

Cupid’s Celeb Choice: Bedford’s own Blake Lively and Ryan Reynolds won’t have to go far from home and their new little addition to have their own romantic celebration a deux.

On-Property Pleasures: Rooftop indoor pool with windowed atrium ceiling serving snacks and lunch; serene 10,000-square-foot spa with a relaxation area featuring curtained, cocoon-like chaise areas perfect for napping; full-service salon; and fitness center with yet more skyline views.

Opt for a couples massage at the spa, a 10,000-square-foot sanctuary atop White Plains.

Nearby Diversions: Catch the latest rom-com at City Center 15 Cinema de Luxe or shop for Valentine’s gifts at The Westchester, both a stroll away.

On-Site Wining & Dining: The smart lobby Lounge with its mesmerizing see-through fireplace for light fare and signature cocktails; chic BLT Steak, with its 2013 Best of Westchester-winning house-baked popovers; and 42 The Restaurant, featuring excelent American cuisine and bird’s-eye views from the 42nd floor.

Pricing: Rates start at $299; $30 daily parking fee. Contact a guest relations staffer for a complimentary rose-petal turndown or any other extravagant Valentine’s requests. The hotel will arrange anything from a marriage proposal to an in-room purchase of an engagement ring to a surprise party—just ask.

1 Renaissance Sq
White Plains

Mayflower Inn & Spa

1¼ hours from White Plains

This fabulous, 58-acre historic country estate, a member of Relais & Châteaux, is an unabashedly romantic retreat and the perfect destination to revel in—or rekindle—a relationship. Thirty exquisitely appointed guest quarters—15 in the manor house and the remainder in smaller buildings—showcase oriental rugs, antique four-poster canopy beds with thick down mattresses, stately fireplaces, and marble bathrooms with mahogany wainscoting.

The Garden Room at The Mayflower Grace, an 84-acre country estate, is bright and luxurious.

V-Day Vibe: Ultra-luxe, country estate elegance

Cupid’s Celeb Choice: Barack and Michelle—anyone who could use a rejuvenating getaway in tony environs away from the stress of everyday life.

On-Property Pleasures: Pamper your love and yourself at the 20,000-square-foot Spa House —foot-warming radiant heated floors throughout—with its mosaic-domed whirlpool, Thermal Sanctuary, and indoor pool purified by bromine, which is gentler on skin and hair than harsh chlorine. Showpiece is its stunning Garden Room with an inviting fireplace and 16-foot-high windows framing an idyllic pond and forest view. Outdoor pool, tennis, and putting green, weather permitting.

Nearby Diversions: Enjoy world-class antiquing in the nearby Litchfield Hills area and nature trails, hiking, cross-country skiing, and snowshoeing at Steep Rock Reserve.

On-Site Wining & Dining: Indulge in a sophisticated dining experience at Muse by Jonathan Cartwright or enjoy hearty pub-style fare in the homey Tap Room. Menus feature fresh organic ingredients, many grown in an on-site greenhouse.

Pricing: $250 per night midweek, $300 weekends; breakfast is not included. Inquire about any special spa packages; details not available at press time.

118 Woodbury Rd
Washington, CT

The Garrison

45 minutes from White Plains

Situated on 300 acres with breathtaking vistas of the Hudson River valley and the mountainous terrain of the Hudson Highlands, this intimate four-room inn is the perfect spot for a tranquil romantic interlude.

V-Day Vibe: Relaxed, unpretentious country charm with a quiet elegance.

One of The Garrison’s four unpretentious guest rooms.

Cupid’s Celeb Choice: With a gorgeous golf course to play in season and snow-covered trails to walk in winter, it’s perfect for active twosomes like Tiger Woods and Lindsey Vonn.

On-Property Pleasures: Besides those astonishing views? A salon, fitness room, and, in season, a golf course.

Nearby Diversions: Browse quaint Cold Spring and Beacon. Or head to Fahnestock State Park for skiing, snowshoeing, sledding, and sipping hot chocolate beside the outdoor fireplace.

On-Site Wining & Dining: Charming and romantic Valley, with its wall of windows and painted wood floors, scored an “Excellent” rating from the New York Times for its seasonal American cuisine that makes use of local ingredients. And the cozy World’s End Bar shares the same enchanting views, but with a casual lounge menu and TV for the sports enthusiast. Outdoor Terrace Grill in season.

Pricing: Room rates vary; includes in-room, help-yourself breakfast with coffee/tea, fresh fruit, yogurt, and granola bars. A special Valentine’s Day five-course dinner menu for $185 will be offered on Thursday, February 12 through Saturday, February 14.

2015 Route 9
Garrison, NY

The Roundhouse at Beacon Falls

1 hour from White Plains

This sleek boutique hotel oozes hipster cool. The refurbished former roundhouse factory and mill buildings, with their gorgeous water views, are home to 23 accommodations, including three suites. The post-industrial design incorporates reclaimed wood and brick and showcases the work of local craftspeople and artists.

V-Day Vibe: Very cool, very hip—a kind of Beacon-channeling-Brooklyn.

The Roundhouse’s 23 guest rooms convey a modern, airy elegance.

Cupid’s Celeb Choice: That trend-setting duo, Brad and Angie.

On-Property Pleasures: A spa is planned for 2016—until then, in-room mass-age and private group yoga sessions are available if booked in advance. Or sit by the sleek modern gas fireplace in the stylish lounge and enjoy artisanal cocktails and a spectacular view of the Fishkill Creek rapids.

Nearby Diversions: Walk along Beacon’s old-fashioned Main Street, lined with charming independent shops, antique stores, galleries, and eateries—do check out Hudson Beach Glass, a gallery/working glass art studio—and visit nearby DIA:Beacon, a modern art museum.

On-Site Wining & Dining: The stunning restaurant featuring Valentine-appropriate red seating—along with a lounge and seasonal outdoor patio—offers excellent, locally sourced New American cuisine.

Pricing: A special Valentine’s “Stay and Dine” package includes a two-night stay, a welcome bottle of Champagne and chocolates, a four-course, prix-fixe dinner for two, and continental breakfast for $679; available only on Friday the 13th and Saturday the 14th.

2 E Main St
Beacon, NY


Looking for more great ways to share your love. Visit our Complete Guide to Valentine’s Day in Westchester.

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