Three Great Vacation Rental Destinations The Catskills, New York
Jupiter Rising (www.jupiterinpisces.com) is a 2-bedroom cabin in the Hunter Mountain region. Larger groups can rent out the adjacent main home (owned by George Lewis, healer and certified astrologer) for a full retreat on the 20-acre property.
While the cabin is rough around the edges and old, including the furniture, it was cozy and intimate, and we knew in advance that we would be spending most of our time on hikes, grilling outside, or lying by the private, heated, outdoor saltwater pool.
The main level comprises a living area with fireplace, spirituality related books lining an entire walled bookshelf, expensive telescope, and a pull-out sofa. There’s a fully equipped kitchen that has a large window looking out to the reservoir and mountains beyond. Atypical for a vacation rental, the cabinets are stocked with food, from fruits to chips and cereal, as well as beverages, and George thoughtfully provided organic toiletries, such as face wash and shampoo, in the windowed bathroom. The all-inclusive rate is $700/night.
Closer to New York City, Fern Hollow (www.vrbo.com), a seven-acre, three-bedroom/three-bathroom craftsman home in Woodstock, New York, served as a quiet sanctuary immersed in nature, a convenient five-minute drive from town and a short distance from trails and ski centers. The host put a lot of detail into the home’s design, including local bluestone floor in the dining room (with large windows overlooking the forest), river stone fireplace, a master bedroom with a new king bed and spacious bathroom with jetted tub, a second bedroom with new queen bed and skylight, and a sun-lit library (with 30” ceiling) that included a ping pong table and flat-screen TV.
Despite visiting in the cold winter, I spent plenty of hours in the backyard, home to a sprawling green lawn, swaying hammock, and a peaceful stream, which my dog Ruby adored. My friend and I took advantage of the outdoor hot tub every day. The Vrbo property is also equipped with a heated, saline pool (which was closed during winter), a reason why this home is high in demand in summer months ($495/ night in low season versus $1,295/ night in high season).
What made both Fern Hollow and Jupiter Rising memorable is that they felt like mini-resorts, especially with the care and comfort pro vided by the hosts.
Puerto Rico has experienced a surge in bookings and with good reason. The island destination located in the Caribbean is part of the United States, so travelers don’t need a passport, nor must they go through hoops of COVID paperwork to arrive.
Puerto Rico is chockfull of luxury resorts with “residence” options, including Dorado Beach, a Ritz Carlton Reserve (www.ritzcarlton.com/en/hotels/puerto-rico/dorado-beach). I consider Dorado Beach not only the best luxury resort in Puerto Rico; it’s one of the best resorts I’ve stayed in (a significant testament considering I’ve stayed in over 650 luxury properties across 113 countries in my career). Originally an estate owned by Laurence Rockefeller in 1958, and graced by famous and powerful guests such as John F. Kennedy and Ava Gardner, Dorado Beach is a 50-acre retreat nestled against the ocean in an utterly pristine and manicured 1,400-ace sanctuary that straddles both rain forest and sea. Guests can expect a crescent shaped beach, infinity pool, infinity hot tub and cold plunge built into the rocks, a Bill Bensley-designed jungle spa, and plenty of high end dining options (the omakase experience is truly decadent). Guests can book one of 14 residences, which are two- to five-bed room accommodations staggered along the beach. Residences, opened in 2013, are each equipped with a private pool (up to 40 feet), washer/dryer, a private butler, and a golf cart, a nice perk to travel between various areas of the property. All residence guests have full access to all resort amenities.
Interestingly, the residences are less expensive that some of the top suites. A two-bedroom residence starts around $5,000 a night, versus a 2-bedroom suite at $8,500 a night. While the larger residences are an ideal option for larger groups, the suites are worth a mention. My two bedroom suite, about 2,000-square feet, was lavish with high tech appliances, each room has an outdoor shower and egg-shaped tub, and a private plunge pool that can be heated.
Whether you book a suite or a residence, Dorado Beach is one of few hotels in all of America where the accommodations are no more than 100 feet away from the sea. Leave your door open a crack at night, you feel like you’re sleeping on top of the ocean. This type of accommodation is extremely rare, and a privilege.
On the other side of San Juan, The St Regis Bahia Beach Resort (www.marriott.com/hotels/travel/sjuxr-the-st-regis-bahia-beach-resort puerto-rico/) is equally luxurious, situated inside a certified Audubon nature sanctuary sprawling 483 acres and adjacent to the famed El Yunque National Forest. Guests are literally immersed in a protected rain forest where it’s not uncommon to see iguanas chilling at the pool or species of rare birds in the wide blue sky. The intimate, glamorous resort hugs an incredibly scenic, three-mile beach with unobstructed ocean views, and art lovers will appreciate the four Fernando Botero bronze sculptures throughout the property. Botero, a famous Colombian artist, is known for his rotund depictions of figures in his art.
You can still feel the resort’s $20 million renovation from 2016: the suites feel like jewel boxes, glamorous and blingy, with views of the sprawling green lawns and palms swaying to the ocean breeze. Gargantuan in size, the private estate residence, Casa Estancias, is considered one of the top vacation rentals on the entire island for VIP and celebrity guests. This five-bedroom residence ($15 to $30K a night) became part of the resort’s portfolio in November 2020.
There’s nothing modest about Casa Estancias. It’s one of the island’s rare homes where the master bedroom includes two master bathrooms, each equipped with rain shower, bathtub, vanity, and walk-in closet.
Every additional bedroom touts its own out door space and private bathroom. Guests can expect a private butler, housekeeping, movie room with 75-inch screen, a massive kitchen with Subzero appliances, and extreme luxury touches, such as a fridge on the second floor (I didn’t have to walk downstairs for a chilled water), electronic blackout curtains, and a motorize flat-screen TV that comes out of a table in the master bedroom (which also included a private study). Most of the exterior “walls” are floor-to ceiling windows, so every inch of the house was flooded with sunlight, including the double height living area connecting to the back yard terrace with 65-foot saltwater lap pool. The oceanfront location made it convenient for us to walk to the resort along the beach, but the property is removed enough to enjoy a slice of beach all by ourselves. Casa Estancias comes with a golf cart, as well as a garage for those renting a car.
With both residences, guests traveling with dogs will be thrilled. The rentals allowed Ruby to run around off-leash since we were removed in our own little oasis.
Palm Springs, California
Nobody knows why Villa Sierra (www.naturaltreats.com) in Palm Springs became Insta-famous for its pink door, not even its owners Sean and Blake Rogers. The villa’s literal pink front door attracted locals, visitors, and influencers who posed out front, and #thatpinkdoor became a viral sensation.
In 2018, Sean and Blake (who have been together for 14 years, and married for 8) opened their vacation home to travelers, offering the opportunity to experience what has now become one of the hottest vacation rentals in Palm Springs.
Villa Sierra is a stunning, 5,300-square-foot, 4-bedroom/4-bath room villa ($1,500-$3,700 per night) that I wouldn’t be surprised to see in Architectural Digest. The mid-century desert ranch, located in the Indian Canyons neighborhood, feels Hollywood glam and desert chic all at once. Floor-to-ceiling windows blur the boundary of inside and outside, and since it is Palm Springs, my friends and I spent most of our time sprawled out in the private backyard sanctuary with towering palms and a 75-foot heated pool and hot tub. The backdrop of the famed San Jacinto Mountains truly gave a sense of place.
With colorful (and expensive) furniture, artwork and design pieces, from chandeliers to luxury ottomans in the marble and glass bathrooms, all rooms are drenched in sunlight with high ceilings enhancing the space. I felt like I was staying at the most exclusive luxury hotel in the area. The interior is just as Instagram–friendly as the pink door (the entire villa feels like a movie set), and there’s plenty of amenities, such as a billiards room, wet bar and separate lounge area with limited edition Claritone stereo, that lured us out of the heated pool at night.