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CATSKILLS, New York

  • NicoleDeRosa
  • 4 days ago
  • 5 min read

While doing some research trying to find the perfect meeting point between New Jersey + Massachusetts for my family, you might assume it’s somewhere purely practical like Bridgeport, Connecticut, which technically sits right in the middle. But in reality, most families (mine included) skip the exact midpoint in favor of somewhere a little more special.


That’s where the Hudson Valley + Catskills come in....



After a lot of research, I’ve found that towns like Rhinebeck, New Paltz + Woodstock hit the sweet spot. They’re roughly 2.5 hours from both North Jersey + much of Massachusetts, making them an easy, balanced drive for everyone. But more importantly, they actually feel like a getaway.


Compared to somewhere like Bridgeport, Connecticut, this region offers:


  • Way more scenic beauty (think mountains, forests + charming small towns)

  • Better options for boutique hotels, cozy inns + vacation rentals

  • A huge range of activities, from hiking + antiquing to wineries + great restaurants


It’s the kind of place where meeting up doesn’t feel like a logistical compromise, it feels like a mini vacation. In this guide, I’ll break down exactly where to stay, where to eat + what to do across the Catskills + Hudson Valley, focusing on my favorite areas: Rhinebeck, New Paltz + Woodstock.




Where To STAY


Click HERE

To BOOK Your STAY In The CATSKILLS



Captain Joseph Allen House - Catskills, NY - A historic mansion listed on the National Register of Historic Places that feels like staying in a private boutique hotel. Sleeps 16+ guests. Has a pool + large entertaining spaces w/ elegant restored interiors.




HUNTER


Scribner's Catskill Lodge - Hunter, NY - Mountain lodge in the heart of the Catskills + home of Scribner's Prospect. Instagram: @scribnerslodge @scribnersprospect #ScribnersLodge #SCLPUpstater #ScribnerHollowPost



ROXBURY


The Roxbury - Roxbury, NY - This Saratoga Springs boutique hotel brand is bringing motor lodges into the 21st century, but keeping the nostalgic vibes intact.



LIVINGSTON MANOR


The DeBruce - Livingston Manor, NY - Historic hotel w/ award winning restaurant perched on 600 acres of Catskills wilderness. Pool, private hiking trails + fly fishing. #TheDeBruce


The Arnold House - Livingston Manor, NY - A cozy, rustic-chic retreat on 80 acres of forested land, known for its tavern, event hosting + relaxed, "unplugged" atmosphere. #SmoreFunUpstate



BIG INDIAN


Urban Cowboy Lodge - Big Indian, NY - A 44 room, boutique hotel offering rustic-luxury, design forward accommodations on 68 acres w/ outdoor cedar soaking tubs, fireplace lounge, Estonian sauna + the Public House restaurant + bar. Designed by: IG: @LyonPorter



PHOENICIA


The Graham + Co. - Phoenicia, NY - A stylishly renovated 20-room motel near Hunter Mountain. Offering a modern, minimalist take w/ a laid back, industrial chic vibe w/ a pool, hammocks, fire pits + complimentary bikes for exploring town. As seen on

Discovery+ and Magnolia Network



NORTH BRANCH


The North Branch Inn - North Branch, NY - An owner operated boutique hotel + restaurant where authentic charm, thoughtful touches + culinary delights are at the heart of your stay.



OLIVEREA VALLEY


Eastwind Oliverea Valley - Oliverea Valley, NY - A Scandinavian inspired boutique hotel w/ 30 rooms + A-frame cabins. A minimalist yet luxurious, nature-focused stay w/ saunas, firepits + the Dandelion restaurant, near Big Indian Wilderness trails + hiking.



WINDHAM


Eastwind Windham - Windham, NY - A boutique, Scandinavian inspired hotel w/ 32 cozy hotel rooms + unique Lushna cabins w/ panoramic views. A romantic, year round stay w/ skiing + hiking w/ outdoor saunas, fire pits + Bunkhouse Lounge.



CALLICOON CENTER


Callicoon Hills - Callicoon Center, NY - A 23 acre retreat w/ 65 casual rooms across a boarding house, deck house + cabins, alongside a seasonal pool, sauna + Conover Club restaurant.


KENOZA LAKE


Kenoza Hall - Kenoza Lake, NY - A restored 1900s lakeside boutique hotel w/ 22 hotel rooms + 10 bungalows) on 55 acres. Full service Hemlock Spa, a lake-view restaurant serving Old World cuisine + private lake access + hiking trails.



ROSCOE


The Yarra - Roscoe, NY - A design forward, 4 room bed + breakfast w/ a cozy, curated experience featuring Australian inspired dining, locally sourced provisions close to the Beaverkill + Willowemoc Rivers.


Roscoe Mountain Club - Roscoe, NY - A 1,000 acre, year round woodland retreat w/ an 18 hole championship golf course, a 24-room inn + restaurant, hiking, fishing + pickleball, catering to both leisure guests + events.



BARRYVILLE


The Darby - Barryville, NY - A stylish, modern, 3 bedroom, 2 bath rental cabin w/ high end amenities like a private indoor sauna. Instagram: @The.Darby.AFrame @Life.At.Darby


Stickett Inn - Barryville, NY - A boutique guesthouse w/ (4) 2 room suites (Drink, Eat, Soak, Steam) + a separate 2 bedroom cottage w/ a modern, rustic getaway near the Delaware River. On-site Bang Bang Bar w/ coffee, cider + food.



MOUNT TREMPER


Howland House - Mount Tremper, NY - A restored 1850s farmhouse inn w/ 10 unique rooms w/ soaking tubs. A cozy stay w/ an on-site bar + restaurant, Oliver's.



TANNERSVILLE


Deer Mountain Inn - Tannersville, NY - A luxury, 168 acre boutique hotel + restaurant w/ an Arts + Crafts style main lodge w/ 6 rooms, 4 private cabins + restaurant w/ panoramic mountain views + hiking trails.






Where To EAT





LIVINGSTON MANOR


  • Sunshine Colony Bar - 47 Main Street, Livingston Manor

  • Upstream Wine + Spirits - 65 Main Street, Livingston Manor, NY (down the street from Sunshine Colony)

  • Stumble Out Bar - 67 Main Street, Livingston Manor, NY - Serving craft cocktails, beer, wine, dinner + weekly specials.

  • Main Street Farm - 49 Main Street, Livingston Manor, NY - A gourmet grocery store

  • The Walk In Manor (The Neon Croissant) - 66 Main Street, Livingston Manor, NY 12758  Coffee, breakfast, lunch + more. Get their cookies + key lime pie!

  • The Kaatskeller - 39 Main Street, Livingston Manor - Wood fired pizzas + cocktails



LEEDS




HUNTER


  • Fellow Mountain Cafe - 7883 Main Street, Hunter, NY - A popular, cozy spot for coffee, breakfast + lunch situated in the heart of the Catskill Mountains, near the entrance to Hunter Mountain.



EAST WINDHAM



BIG INDIAN


  • Eastwind Oliverea Valley Bar - 212 McKenley Hollow Road, Big Indian, NY - Located inside the Eastwind Olivera Valley Hotel

  • Dandelion Restaurant - 212 McKenley Hollow Rd, Big Indian, NY - Also located inside the Eastwind Olivera Valley Hotel



HENSONVILLE


  • Matilda - 39 Goshen Rd, Hensonville, NY - A restaurant located inside The Henson Hotel

  • Paracasa Bakery - 391 NY-296, Hensonville, NY



CALLICOON




ROSCOE



Things TO DO






MOUNT TREMPER


  • Kaaterskill Falls - 5096 Route 28, Mount Tremper, NY - A two-stage waterfall on Spruce Creek in the eastern Catskill Mountains, between the hamlets of Haines Falls + Palenville in Greene County



HAINES FALLS


  • Sunset Rock Trail - 874 N Lake Rd, Haines Falls, NY - A 4.6-mile hike w/ mild to heavy foot traffic. This loop is also connected to Artist's Rock, Newman's Ledge + Mary's Glen Trail.



CALLICCON




NORTH BRANCH




HUNTER




LONG EDDY


  • La Valley Estates - Long Eddy, NY - An enchanting private estate, 172-acre wedding venue + event retreat located in the Western Catskills. It functions as a vacation rental + event space featuring a farmhouse that sleeps up to 30 people, a barn for events + 6 cabins.



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