Valentine’s Day countdown: Start booking your romantic hotel stays now!

See recent posts by Kelsey Blodget

Book Room at The Jefferson hotel in Washington, D.C.
Book Room at The Jefferson hotel in Washington, D.C.

We know, we know – Valentine’s Day is still more than a month away, and you haven’t even started thinking about how you’re going to surprise that special someone. But why not get ahead of the game for once? Instead of buying a last-minute scarf or struggling to get a table at a trendy restaurant, consider booking a getaway weekend at one of Oyster’s favorite romantic hotels. And if you think your significant other might need a little prodding, try dropping a subtle hint, like printing out this list and placing it on his or her pillow.

Below, we’ve selected our favorite places for some tender alone time in each of our destinations.

Fifteen Beacon

This luxury boutique surrounded by hidden gardens, antique shops, and the gorgeous brick Federal-style homes of Beacon Hill, is the perfect choice for couples looking to heat things up on a cold New England night. Every spacious but cozy room has a gas fireplace. And the phenomenal, highly personalized service includes an evening turndown that transforms the rooms into soothing relaxation dens — dim lights, a crackling fire, and soft classical music.

Sivory Punta Cana

Made up of 55 massive suites, the Sivory is surrounded by dense tropical plant life and sits on one of the most remote stretches of Punta Cana (a 90-minute drive from the airport). Every suite features a two-person Jacuzzi tub, a two-person shower, and a private, intimate balcony — all ideal for a romantic getaway. In addition to its premier spa with outdoor “bucket” showers, the hotel has three exceptional restaurants on-site.

The Jefferson

An elite luxury boutique hotel, the Jefferson spoils couples with impeccable service, exceptional spa (which offers “vinotherapies” to reflect Thomas Jefferson’s love of wine), and charming details like the cozy library with a fireplace and the working dumbwaiter that delivers wine bottles from the hotel’s 1,000-bottle cellar.

Hotel Hana-Maui

Situated along craggy coastal cliffs on the rainforest-like east coast of Maui, hours from other big resorts, the Hotel Hana-Maui offers guests ample chances to be alone. After hikes to nearby waterfalls or hunts for hidden beaches, couples can take a dip in the infinity pool or the Honua Spa’s outdoor lava-rock pool, dine at the excellent restaurant, and then retreat to spacious modern cottage suites (some with private hot tubs), where guests will find no phones, TVs, radios, or alarm clocks to spoil the mood.


These five modern villas on a remote mountaintop are cut off from prying eyes by thick stone walls and dense flora. Designed for utmost privacy, there’s no communal pool, lobby, or front desk. Service is by request only, and each room comes with a cell phone so guests can call anyone from room service to the free staff driver to the hotel’s owner. The rooms are self-contained sanctuaries with the 24-hour room service, in-room massages, free Wi-Fi, and the pre-programmed Apple TVs set with cult movies or eclectic reggae. Frenchman’s Cove, one of the most beautiful beaches in the world, is 10 minutes away.

Encore at Wynn Las Vegas

Opened in December 2008 by famed Vegas developer Steve Wynn, the 2,034-room Encore takes the whim and luxury of its sister, the Wynn hotel (opened in 2005) and improves it with even bigger rooms and a more attractive spa and fitness center. The classy, adults-only European Pool and beautiful suites with floor-to-ceiling windows, electronic bedside drape control, a comfortable lounge area in even the base-level rooms, and a decadent bathroom make the Encore a premier pick for couples.

Hotel Casa Del Mar

A location right on the sand (one of only two L.A. hotels with this feature), gives Santa Monica‘s luxury Casa del Mar plenty of opportunity to exploit stunning, romantic views — be it from the 5th-floor rooftop pool and hot tub, the large, sumptuous suites with Jacuzzi bathtubs, or the elegant Veranda restaurant with its 20-foot high windows. Couples can sip cocktails and listen to live nightly jazz in the intimate lobby, enjoy private in-room massages — or take them poolside in the ocean breeze — and walk barefoot on the beach just a few feet from the hotel. An excellent, accommodating staff that’s keenly respectful of privacy ties it all together.

Fisher Island Hotel And Resort

Built in 1925 as William Vanderbilt II’s winter estate, Fisher Island feels like it’s from another era: Peacocks roam the property and tuxedo-clad waiters know residents by name. In hip, glitzy Miami, Fisher Island is a welcome taste of old-world romance, and its location on the private 216-acre Fisher Island is as secluded as it gets. It doesn’t have the high-design rooms or gourmet restaurants that you’ll find in Miami’s other luxury hotels, but it compensates with its history and charm. Couples should opt for the 675-square-foot courtyard gardenview villas, which are located in the beautiful garden at the resort’s entrance and have private terraces with their own Jacuzzis.

Gramercy Park Hotel

Pillow-top mattresses, luxuriously heavy comforters, and velvet throw blankets make these beds perfect for spending lots of time in. The old-world, boho-chic decor accentuates the romantic vibe, and the English Drinking cabinet — essentially a flip-down bar — allows couples to enjoy stylish cocktails without going anywhere.

The Huntington Hotel

Nob Hill, San Francisco’s swankiest neighborhood, is home to many of its grandest hotels — stately old buildings with cavernous marble-filled lobbies and hundreds of rooms. By contrast, the elegant 136-room Huntington Hotel is more intimate and unassuming. Yet it’s just as luxurious as its neighbors. The spacious, newly renovated rooms overlook either the city or quiet Huntington Park across the street. The formal staff is attentive, yet discreet. The hotel’s Nob Hill Spa is one of the city’s best, and guests can use its indoor pool and lounge with a fireplace for free.

Prices updated 1/29/10

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