Newport, Rhode Island
The Gist: Secluded on a peninsula away from downtown Newport, this year-round resort has a prime oceanfront location with two private beaches.
Sleep: Rooms and suites fall into three categories: “On the Hill,” “By the Beach,” or “Overlooking the Harbor.” The Private Beach Cottages take full advantage of Castle Hill’s location, with semi-private decks overlooking the sand dunes, New England-chic wicker furniture, and, often, fireplaces. For the best views, book the bi-level Turret Suite on the third floor of the Agassiz Mansion, with 320-degree panoramas of Narragansett Bay, the Atlantic Ocean, and Castle Hill Lighthouse.
Do: From Gilded Age mansions and Cliff Walk to the grass courts at the International Tennis Hall of Fame and the annual Newport Jazz Festival, there’s plenty to do in this tony Rhode Island town. But, part of the pleasure of Castle Hill Inn is escaping the hustle-and-bustle to sunbathe and swim in the calm waters at sandy Castle Hill Beach. Also worth indulging in is the hotel’s dining. The formal, wood-paneled Dining Room is considered one of Newport’s top spots for a special-occasion meal, while the more casual Lawn is the place to kick back with a craft cocktail, lobster roll, and quintessential coastal New England view.
You’ll Love: The smaller, more secluded of Castle Hill Inn’s two beaches, pebbly Grace Kelly Beach is where the soon-to-be princess (and bridal-fashion icon) sunned between takes of High Society in 1956.
Rates: from $1,025/night
The Gist: Yes, it’s a major splurge, but this luxe, adults-only, all-inclusive property on Sinclair Lewis’ former farm-estate consistently ranks among the world’s most romantic hotels for a reason.
Sleep: There are a handful of tastefully appointed rooms, but most guests opt to stay in the exquisite private cottages, which have won’t-want-to-go-outside features, like extra-deep stone hot tubs, wood-burning fireplaces, cast-iron-and-copper soaking tubs, and picture windows looking out on the verdant Vermont countryside. Two of the most romantic are Aviary, with walls of windows and a natural-stone hot tub nestled next to the fireplace, and the 3,000 sq. ft. Chalet, with two fireplaces and exposed birch beams.
Do: Fall into the rhythm of a stay at Twin Farms. Hike, bike, or ski on private trails (and have the concierge leave a lobster picnic for you); play croquet on the lawn or billiards at the pub; relax with a hand-carved Stave jigsaw puzzle; or hole up in your cottage with Netflix, truffle popcorn, freshly baked cookies, and a bottle of Champagne. Whatever you choose, don’t miss dinner: The daily tasting menus are a highlight of any stay, featuring pairings chosen from the 15,000-bottle wine cellar.
You’ll Love: Twin Farms saves details of guests’ stays, from the cottage you loved to your aversion to bleu cheese, so you’ll have a seamless experience should you choose to return (hint: for an anniversary!).
Rates: cottages from $1,650/night
The Gist: In bucolic Litchfield County, 113 acres and a destination-worthy spa make Winvian the perfect place to reset after wedding planning and partying.
Sleep: Eighteen eclectic cottages, each with its own distinct theme and design, comprise the accommodations here. Booking well in advance is advisable to snag the concept that most speaks to you, whether it’s Charter Oak, built around a massive tree; dog-friendly Connecticut Yankee, with its English-castle-inspired décor; cozy Library, featuring a roaring fire, leather seating, and book-lined mezzanine; or Instagrammable Treehouse, suspended 35 feet above the forest floor.
Do: Book yourselves some time at the 5,000 sq. ft. spa, offering fireside massages, hydrotherapy treatments, a sauna, and, in warmer months, a 40-foot pool tucked into a meadow. Once you’ve been thoroughly pampered, take advantage of the bikes provided with each cottage to explore the tree-lined paths, small ponds, and organic gardens; arrange a private cooking class; and have a romantic dinner in the fire-lit, 18th-century dining room.
You’ll Love: Weather permitting, there’s no better way to see surrounding Litchfield County than in Winvian’s hot-air balloon.
Rates: from $699/night
The Gist: For anyone who’s ever dreamed of having a home on this preppy paradise, there’s this high-design boutique hotel that’s the definition of #DreamHome.
Sleep: Design firm Roman and Williams transformed an 1850s Greek Revival home into this gorgeous showpiece of sea- and history-inspired design. The 20 rooms and suites feature reclaimed chestnut floors; whitewashed walls; worn leather armchairs; oh-so-chic, blue-and-white, block-print bedding; and hand-painted, Dutch-and-Moroccan-tiled walk-in showers that depict scenes from Nantucket’s seafaring past.
Do: Grab the complimentary beachbag from your room — it’s stocked with blankets, towels, flip-flops, sunscreen, and portable Bose Bluetooth speakers — and stake your claim on a swath of sand. The center-of-town location means you’ll never want for things to do, but it’s still worth asking the dialed-in concierge to upgrade your itinerary with recommendations for the best boutiques and hidden beaches or bespoke experiences, like private sightseeing tours and beachfront dinners.
You’ll Love: Dinner al fresco at Via Mare, Greydon House’s Venetian-inspired restaurant serving locally sourced small plates, cocktails, and an eclectic selection of wines by the bottle.
Rates: from $600/night
Montreal, Quebec, Canada
The Gist: With its prime location in Old Montreal — the closest you’ll get to a European escape without a plane ticket — this relatively affordable hotel is a cozy abode in the big city.
Sleep: Spread across four historic buildings, the 105 rooms and suites at Hotel Nelligan feature original exposed brick and stone details. Even the coziest rooms have massive-for-a-city-hotel-sized marble baths with walk-in showers, but it’s worth spending a little extra for a Petite Suite with views of Old Montreal and a gas fireplace for chilly Canadian nights.
Do: There’s plenty to fill your days within walking distance, from art galleries and restaurants to fashionable boutiques to blow some of your wedding-gift money. Back at Hotel Nelligan, check out the on-site restaurants, French Verses Bistro and Mechant Bouef brasserie, where you can split an upmarket version of the city’s famed poutine with beef brisket, veal stock, and cheese curds; a dry-aged porterhouse; and a bottle of wine from nearby Niagara vineyards.
You’ll Love: Terrasse Nelligan, the hotel’s rooftop restaurant/bar with sweeping views of Old Montreal, including the Basilique Notre Dame and Vieux Port, is the perfect place to toast your newlywed status.
Rates: from $220/night