8 Guest Houses to Host with the Most
There’s an old adage that guests, like fish, begin to smell after three days — but it doesn’t have to be that way. When everyone has personal space to unwind, welcoming visitors can be a downright delight — whether for an overnight stay, a holiday weekend, or even longer. These listings with guest houses across Corcoran’s network ensure you’ll always be prepared to accommodate company in comfort and style.
Unpack those bags, head to Instagram, and tell us in the comments which guest house would let you host with the most.
Sunset Farm is the type of idyllic setting where the world outside feels like a distant memory. Basically, get ready to host some guests. A two-bedroom guest cottage awaits right alongside one of the property’s five freshwater ponds, tucked away from the main home and a gigantic barn to foster a marvelous sense of solitude. Stare idly across the emerald landscape, wander the sprawling meadows, watch the geese wade, or make your way to Cape Cod Bay. Spending time here is time well spent. Despite being a getaway, this home keeps close to historic downtown Sandwich’s restaurants, shops, and galleries.
Listed By: Brian Dougherty of Corcoran Property Advisors.
You’d be hard-pressed to meet a guest who won’t make the pilgrimage and pay tribute to this estate, dating farther back than most can chart the branches of their family trees. But this former 12th-century Cistercian monastery possesses far more than a CVS receipt-sized lineage. Its guest housing encompasses 16 bedrooms across five distinct quarters, some featuring sitting rooms and fireplaces. Common areas such as a wood-paneled library, a covered breakfast porch, a heavenly pool area, and a Turkish bath make staying over all the more enticing. For further Portugal adventures, the property is near historic villages, UNESCO World Heritage sites, jaw-dropping parkland, and wine regions.
Listed By: Dieter Rauch of Corcoran Atlantic.
When a stunning standalone home to call their own isn’t enough for certain discerning guests, give them a lawn, too. After all, there are five acres to work with at this Water Mill residence. In terms of style and substance, this picturesque countryside guest house features vaulted wooden ceilings and paned windows among its two bedrooms, one bathroom, and kitchen. Should entertainment await within the immense main home, or on its covered bluestone patios, take the short stroll. Along the way, you’ll come across a drop of blue in the splendidly still ocean of green — a heated gunite pool.
Listed By: Sheila Smith of Corcoran’s East Hampton Office.
If guests are getting the chance to stay at a waterfront escape on Culebra, odds are they’ll be all too taken with the island’s glorious beauty to care much about accommodations. Luckily for them, however, this coastal property is all about the guest experience. Club Seabourne is built for hospitality, featuring tropical style and substance and unbeatable Fulladoze Bay vistas. A central communal swimming pool and an on-site restaurant and bar join its 13 welcoming villas. Throw in adventures in boating, snorkeling, diving, fishing, and general aquatic exploration via the dock (which boasts four moorings), and you may find yourself with a robust waiting list of potential visitors.
Listed By: Juan Eliel Woychejoski and Maria Eugenia Del Valle of Corcoran Puerto Rico.
Where the Hudson Valley and Berkshires blend into one, discover a breathtaking mountaintop estate. Although technically under one long roof, the guest house stands apart from its main counterpart with two bedrooms, a living area, and a windowed bath. From all of these rooms, you can take in a few angles of the 31-plus-acre property’s 360-degree landscape panoramas, comprising New York and Massachusetts at their bucolic best. There’s a surreal, optical illusion quality to the main house and the pool house, designed in such a way that it appears a cross-section between them has been excised. No matter, however, considering the dreamy infinity pool area that links them.
Listed By: Jason Karadus, Louis Naccarato, Ryan Wexler, and Marie-Claire Gladstone of Corcoran Country Living.
Across nearly four acres, this sprawling compound supplies space and serenity alongside true Santa Fe style. After watching the sunset from the main home’s panoramic valley overlook, overnighters have their pick of self-contained stucco-clad retreats. Nearby, one guest house sports handcrafted vigas beams throughout, plus living and dining areas, a full kitchen with a pass-through window, two bedrooms, and a bathroom. On the property’s southern end, three domed residences add architectural variety while simultaneously serving as charming quarters. When not inhabited by friends and family, these bonus spaces can as easily become studios, offices, reading nooks, and the like.
Listed By: Harrison Bingham of Corcoran Plaza Properties.
This guest house waltzes in tandem with its main counterpart, each constructed from local fieldstone and exuding textbook historic appeal. Dating to 1833, the property was previously the site of a church and its detached schoolhouse. These days, the former still boasts its original door and vaulted ceilings, while the latter is a 714-square-foot space with a living room, kitchen, bedroom, and full bath — all between four walls of fieldstone. A wood stove only amplifies the endearingly throwback vibes and keeps things extra cozy in the colder months. Elsewhere, a deck provides a private outdoor area. Exploring the three-plus-acre grounds reveals walking trails, gardens, a two-story barn, and more.
Listed By: Joe O’Hara and Susan Thomas of Corcoran McEnearney.
Everyone gets a personal piece of island elegance at this home, poking out of the sloping hillside above Eustatia Sound. Things can’t help but gravitate to the main residence’s standout great room, which flaunts floor-to-ceiling windows and exists in indoor-outdoor harmony with an infinity lap pool. Yet, four freestanding cottages form a striking ensemble. Each features a bedroom, a bath, and a balcony that overlooks the crystalline water by day and bathes under a sea of stars by night. And, if desired, you could even enjoy the view while still lying in bed — an ideal place to laze and gaze into the infinitely expanding horizon.
Listed By: Glenroy Mark and Adrienne Harris of Corcoran BVI.
