This content originally appeared on our newsletter, The Itinerary: Catskills Cloud House in Phoenicia, NY, mailed on 4/12/24. Want to get news like this, straight to your inbox? Sign up for the Escape Club, where upgraded paid membership also gets you exclusive discounts on Upstate getaways you won’t find anywhere else.
Photos: 3, 5, 8-10 by Escape Brooklyn. 1, 7 by Catskills Cloud House. 2 by Kate Jordan. 8 by Caitlin Guy.
Welcome to The Itinerary: Your go-to guide for easy Upstate escapes – plus exclusive discounts for each – created by Escape Brooklyn.
The Location:
Catskills Cloud House in Phoenicia, NY.
The Deal:
Paid subscribers get 15% off, now through May 23, 2024. Find the code beneath the paywall.
Why We Love It:
This airy farmhouse is located in sleepy Phoenicia, New York, whose town has a full-time population of 268. Bordered by the Esopus Creek, its Main Street is ringed by the high peaks of the Catskills – giving a sense of place, which is, deep in the mountains.
The cherry on top? Surrounded by wilderness, Catskills Cloud House is one of the few Catskills Airbnbs that’s accessible without a car.
The Vibe:
An Escape-Worthy Itinerary: Catskills Cloud House in Phoenicia, NY
In & Around Woodstock and Phoenicia, NY. Photos by Escape Brooklyn.
Friday: Check-in & Check Out
• 7 pm: The kitchen at Catskills Cloud House is such a dream – it’d be a crime not to make a meal here. Use the kitchen as your social center while making dinner, then continue the dinner party outdoors on the deck. When that’s over, move to the stone fire pit on the far side of the yard for drinks and stories under the stars.
Saturday: Hike to 1800’s Hotel Ruins, Lunch on a Mountaintop, and Explore Woodstock, NY
• 9 am: Pack up and head to nearby Woodstock for a hike at Overlook Mountain Trail, about 30 minutes from the house. On your way to the trail, stop into Mud Club or Bread Alone and grab a to-go style lunch to enjoy on the trail.
• 10 am: As a heads up, parking at Overlook Mountain Trail is limited; arrive before 10 to get a spot. The 4.6 mile trail climbs to the ruins of a grand hotel dating to the early 1800’s; a series of fires spelled its demise. Just past the hotel, climb the stairs up Overlook Mountain’s fire tower for unparalleled 360º views of the Catskills. Make note of the reservoir below; you’ll be heading there tomorrow!
The entire trip, plus time at the top to eat, takes about three hours.
• 1 pm: Head back to Main Street Woodstock for some shopping, including their weekend flea market, open both Saturday and Sundays. Some favorite shops in town include Three Turtle Doves, Shop Little House, Anatolia Rugs, Fruition Chocolate, and The Golden Notebook. There’s a few art galleries and artisan shops to pop into, as well.
• 4 pm: We love Early Terrible for a late afternoon drink and cheese plate. This natural wine bar with an amazing yard serves tapas-style snacks, plus a short menu of more substantial food. If beer and breweries are more your vibe, opt for Woodstock Brewing on your way back to the house to sample some local brews – plus a full menu including sandwiches, tacos, and sharable snacks like quesadillas, chips wings (vegan option included!)
• 7 pm: There’s a load of great restaurants in the area, but we keep going back to The Pines. The lodge-like roadhouse has lovely dining areas both inside and out, and a casual-but-refined menu. Check their Instagram page for seasonal offerings and event listings.
(Honorable mention: we also adore nearby Foxfire Mountain House – but since this hotel frequently hosts weddings, its dining room isn’t always open to the public.)
• 9 pm: After all, it’s vacation – if you feel like you could keep going, check out the local bar scene and load up the jukebox at Sportsman’s Alamo Cantina, walkable from the house. (FWIW, their adjoining business Brio’s has a sesame-crusted pizza that is amazing, if you can squeeze that into your schedule.)
Sunday: Brunch at a Famous Diner, Walk the Ashokan Reservoir and a Pit-Stop in Kingston, NY
• 11 am: Have a slow morning at Catskills Cloud House before check-out at 11. Pack up the car, then park in town to explore Phoenicia’s Main Street. We love old-fashioned country shop Nest Egg for a kitschy souvenir!
• 12:30 pm: It wouldn’t be a trip to Phoenicia without a meal at Phoenicia Diner. Traditional diner favorites are served at this roadside diner using seasonal, local, fresh ingredients. Have your phone handy and ready for this very Instagramable location.
• 2 pm: Make your way to Ashokan Reservoir Promenade to bid the mountains adieu. The 2.8-mile trail hugs the southern shore of the massive Ashokan Reservoir, which supplies 40% of New York City’s water. Perfect for a pic on the way out of town, or a leisurely walk.
• 4 pm: If you’re not too keen on rushing back to the city, spend a few hours in Kingston, NY. We love shopping in the Stockade District, or walking up and down the hills of the Rondout area. For more specific recommendations, check our full Guide to Kingston.