5 Luxe Fall Weekend Escapes Near Boston

When it comes to picturesque escapes, New England boasts a collection of charming destinations that offer a blend of history, luxury, and natural beauty. Whether you’re seeking a tranquil retreat in the Berkshires or the coastal splendor of Newport and Kennebunkport, these five exceptional properties provide unique experiences for guests during the fall season.

Photo Credit: Twin Farms

Twin Farms

Discover Twin Farms, a Vermont oasis nestled on 300 acres of natural beauty located just 90 minutes from Burlington, VT. Escape to this peaceful retreat featuring 28 individually crafted cottages and suites, adorned with contemporary art. Twin Farms’ newest accommodation features eight treehouses hovering up to 20 feet off the ground and reached only by bridge. The treehouses immerse guests in nature with their bespoke, hand-carved wood details, a soaking tub with expansive treetop views, and a large private deck for bird watching.

Guests can also engage in nature with on-site activities like biking, hiking, archery, axe throwing, a bee tour, or retreat to the Bridge House Spa for a massage, then take delight in the warm waters of the furo, a Japanese-style bathhouse.

Celebrate Vermont’s seasons with farm-to-table cuisine at the main dining room. Here, wine enthusiasts will delight in the extensive 15,000-bottle cellar, featuring a diverse range of wines from established Californian and French estates to up-and-coming vintners worldwide. For those seeking a premium experience, Twin Farms’ exclusive reserve wine list presents a select offering of world-renowned bottles. Further, elevate your culinary journey with unique experiences such as a private dinner hosted in the Wine Cellar. If you choose to dine while disconnecting, head to a secluded forest or sit pondside by a firepit with mountain views while you feast on a gourmet, expertly packed picnic. Twin Farms’ latest culinary destination is Twigg’s, offering a laidback, contemporary vibe where diners can sip handcrafted cocktails and/or local brews while savoring Vermont cheeses and crave-worthy burgers and steaks cooked on an Argentinian wood-fired grill.

452 Royalton Turnpike, Barnard, VT 05031

Photo Credit: Wheatleigh

Wheatleigh

Escape to a private sanctuary in The Berkshires at the Wheatleigh, an Italianate-style country home that is on the National Register of Historic Places because it once housed the late Henry Cook, a New York-based railroad and banking tycoon. Cook named the property Wheatleigh because he was inspired by his ancestral family home in Wheatley, Oxfordshire.

Photo Credit: Wheatleigh

Step inside the elegant Gilded Age mansion built in the style of a Florentine palazzo surrounded by a Fredrick Law Olmsted-designed Park. The hotel boasts original details, including Tiffany windows, and features 19 sophisticated, artfully designed guest rooms and suites showcasing high ceilings, fine antiques, and museum-quality art.

Check out Wheatleigh’s newly reopened fine-dining restaurant, Sage & Sparrow for a tasting menu-only experience that highlights the best of the Berkshire proteins and flora. Menu highlights include Bluefin Tuna Belly with juniper and shiso, cold pheasant broth with caviar and raw cream, Fermented Pumpkin Seed Risotto with truffle and aged reggiano, Turbot with white boar pumpkin and pear cider, and Black Garlic Custard with matsutake mushrooms and spruce in a fowl jus.

Hawthorne Rd, Lenox, MA 01240

Photo Credit: The Chanler at Cliff Walk

The Chanler at Cliff Walk

Craving a cliffside escape with a dash of history? Dive into The Chanler at Cliff Walk in Newport, RI, once the summer haven of Congressman John Winthrop Chanler. Here, 20 opulent rooms with fireplaces await or level up with a Garden or Ocean Villa featuring private outdoor entrances.

For dining, delight in modern delicacies, blind tastings, and wine pairings recognized by Wine Spectator’s Award of Excellence, at Cara with panoramic ocean views, or sit back and enjoy views of Easton’s Bay with prix fixe menus at The Café. Step back in time at The Lounge with rich upholstery and custom wallpaper to sip vintage spirits, bespoke cocktails, and an extensive wine collection. Don’t miss the seasonal Apple Cider Bar for a New England treat open on weekends now through November 19 where guests can savor Rose Hill Heirloom apple ciders and liqueur-infused options

Photo Credit: The Chanler at Cliff Walk

End your day with an in-room massage and/or butler-drawn aromatherapy bath with Aromatherapy Associates essential oils to melt your cares away.

Seeking adventure? Head into Newport for shopping, gilded-age mansion tours, sailing excursions, and more with the in-house Cadillac car and chauffeur.

117 Memorial Blvd, Newport, RI 02840

White Barn Inn, Auberge Resorts Collection

Your fall adventure begins in the scenic coastal town of Kennebunkport at the rustic, charming White Barn Inn, Auberge Resorts Collection.

Embark on a fall journey in Kennebunkport at the quaint White Barn Inn. Select from two Barbour-themed fall activities: the ‘Fall Foliage by the Sea’ tour, showcasing Maine’s lighthouses and Casco Bay’s autumn hues, with a stop at an oyster farm and ending with a fireside Smokeshow Cocktail, White Barn’s interpretation of a Manhattan, accompanied by a special sausage roll from Chef Mat, a nod to Barbour’s British origins. The second excursion is the ‘Private Autumn Farm Tour,’ introducing guests to Spring Creek Farm’s sustainable farming practices where guests can engage in the daily farm operations and meet the animals.

A trip to White Barn Inn isn’t complete without a visit to its iconic dining establishment, White Barn Inn Restaurant, now celebrating 50 years. With its special, long-standing relationships with the farmers, fishermen, and foragers of coastal Maine, the restaurant brings fresh, seasonal culinary experiences to its guests. There will be a commemorative 50th Anniversary Dinner on November 3-4, where returning chefs collaborate with Executive Chef Mathew Woolf.

Photo Credit: White Barn Inn, Auberge Resorts Collection

For a laidback, relaxed vibe, head to the Little Barn to sample a Provisions menu along with Chef Mathew’s daily menu board with local favorites.

For a restorative experience, head to The White Barn Spa for the Raindrop Therapy, a tranquil treatment based on Native American wellness traditions using essential oils that are applied like drops of rain.

37 Beach Ave, Kennebunk, ME 04043

Photo Credit: Stonehurst Manor

Stonehurst Manor

Embrace the enchanting glamour of a 19th-century manor offering unbelievable amenities and scenic New Hampshire landscape views. This pet-friendly hotel provides 16 cozy rooms and private condos with wood-burning fireplaces, relaxing whirlpool baths, and expansive views of the surrounding White Mountains to give you the ultimate retreat from the city.

Indulge in classic New England fare with an Italian twist at the welcoming Wild Rose Restaurant with homemade wood-fired bread and pizza, fresh daily seafood from Maine, and pasta dishes to satisfy all your cravings. A bonus! Breakfast and dinner are included in the cost of your stay.

Photo Credit: Stonehurst Manor

When you’re ready for a tipple or two, head to the warm and inviting Library Lounge to sip back in a leather chair and savor an award-winning cocktail infused with locally sourced ingredients made by expert mixologist Michael Rego. We recommend Mr. Bigelow’s Basil-Tini concocted with orange bitters, vodka, pineapple juice, basil leaves, simple syrup, and fresh lemon juice.

3351 White Mountain Hwy, North Conway, NH 03860