Whether you retreat to a Berkshires estate landscaped by Frederick Law Olmsted or to a boutique inn on Shelter Island, the rooms at the following breathtaking destinations will quickly fill up with winter weary travelers—and you’ll want to be one of them.
Wheatleigh Hotel | Lenox, MA
If ever there was a time to use the word enchanting, this is it. Wheatleigh’s setting is something out of a Jane Austen novel—its 22-acre park was originally designed by Frederick Law Olmsted—and though its location in the Berkshires near Tanglewood and charming towns couldn’t be better, you won’t want to—nor need to—leave the hotel grounds for a thing.
How to get there: Take Peter Pan bus to Lenox, MA. One-way tickets are from $40 and the ride takes 4 hours.
Weekapaug Inn | Westerly, RI
You could easily spend a day lounging on the private white sands of Weekapaug Beach, reading a book against the backdrop of Block Island, Montauk and the Rhode Island coastline. But you’ll likely be tempted to celebrate spring by biking to Watch Hill, kayaking around the inn’s estuary, playing croquet, or sailing a restored Beetlecat on Quonochontaug Pond. The Weekapaug Inn offers many other complimentary activities, including daily culinary classes, spa and wellness clinics, and astronomy nights. After a $20 million renovation, the property reopened in 2012 with farm-to-table dining options and 31 rooms and four suites with a modern-meets-colonial revival aesthetic as soothing as the views outside your window.
How to get there: The Westerly station is located 15 minutes from the Weekapaug Inn, on Amtrak’s Northeast Regional line (one-way tickets are from $55 and the ride takes 3 hours). Call the hotel in advance to arrange for transportation to and from the Inn.
Bedford Post Inn | Hudson Valley, NY
A getaway to the Bedford Post Inn, owned by Richard Gere, is a simple, elegant and dependable escape. Here, you eat at newly opened Campagna, do praying mantis in the yoga loft, and love the peace and quiet of an afternoon by the pool. After exploring the hiking trails surrounding the inn, you’ll take a bath in a clawfoot tub in a mosaic-tiled bathroom, and go home on the train feeling completely rejuvenated and ready for whatever the new season has in store. For more information about the hotel, read oM’s full review.
How to get there: Take Metro-North to Bedford Hills Station, then a cab ride ($25) to the inn. The train ticket is $12.75/one way off peak and the ride takes 69 minutes.
Jedediah Hawkins Inn | Long Island, NY
Built in 1863 by a ship captain named Jedidiah Hawkins, this inn alone is worth planning an overnight getaway to the North Fork. After you’ve arrived at the hotel, tucked away on an unassuming road with hammocks and chickens and 22 acres of gardens and farmland, you won’t know what to do first: start with a tipple in the solarium or speakeasy and then enjoy some of the complimentary wine tastings provided by the inn’s 14 vineyard partners; or take out a free bike and head three minutes away to Jamesport beach before returning for boozy bocce ball. Between yoga and painting classes, make sure to inquire about the inn’s intriguing history (complete with secret passages and trapdoors).
How to get there: Take Hampton Jitney to the Jamesport stop, then a five-minute walk to the inn.
The Chequit | Shelter Island, NY
There are a couple of fantastic Salt Hotels properties at Shelter Island including the Eben House, opened in May 2015 in Provincetown, and The Chequit. Though there is much to see a short ferry ride away, you won’t want to get off the island after you experience the refreshing makeover this inn has received. The sweeping views of the harbor and five-minute walk to the ferry docks haven’t changed, but it’s the new chic décor and delicious complimentary farm-to-fork breakfast in bed that will make your visits to Shelter Island a recurring theme this spring and summer.
How to get there: Take the LIRR or Hampton Jitney to Greenport, then the North Ferry, a short five minute walk from the hotel and connects to Greenport on the North Fork of Long Island. Both ferries run throughout the day but are first come first serve so be prepared to wait during peak travel periods.
Gedney Farm | New Marlboro, MA
Gedney Farm will have you at the big red barn. The Berkshires has always been a seductive lady of a landscape and this charming complex, comprised of former stallion stables inspired by 19th century Normandy barns, will have you wondering what else has been hiding in the highlands of western Massachusetts.
How to get there: Take Peter Pan Bus ($38/one way ticket) to Sheffield, MA, then a 20 minute cab ride to the farm.
The White Hart | Salisbury, CT
There’s not a lot to do around here, which is almost the point. There’s just the right amount of things and people to enjoy. This historic Malcolm Gladwell-backed inn has Trivia Night and really good British comfort food, and the bar snacks are house-made crispy pork rinds with onion and crème fraîche dip. Everything about the old-new house at 15 Undermountain Road is travel-worthy, even though it doesn’t have many tricks to offer, that’s sort of the beauty of it. If you’ve come from a small, overstuffed apartment, The White Hart inn’s airy minimalism is a welcome sight, like a silkier, dreamier dressed-up version of your life—filled with lots of interesting drunk locals—you just want to linger in a little longer.
How to get there: Take a two hour Metro-North ride to Wassaic Station ($19.50/one way off peak), then a 30-minute cab to the inn. Or consult oM’s guide to renting hybrids in NYC.
Otesaga Resort Hotel | Cooperstown, NY
Before the shores of Lake Otsego are filled with summertime crowds, have this 700-foot stretch of lakefront mostly to yourself this spring. Settle into a rocking chair on the 180-foot veranda, sink into the heated outdoor pool, or paddle through “Glimmerglass” lake in a canoe. Consider booking the Hello Spring package (20% off, valid through May 22), which includes accommodations, breakfast, and a bottle of signature wine.
How to get there: Take Adirondack Trailways bus to Cooperstown. The trip takes 5 hours 40 minutes and costs $55 one way.
The co-founder and editor-at-large at offMetro, Lauren is a sustainable travel specialist and freelance journalist with frequent bylines in National Geographic, Bicycling Magazine and Shape. Follow Lauren’s adventures at @laurenmati.
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram