December Escapes Are In! 🌲🎁 + Cyber Monday
25% off ski getaways, $200 off lakefront retreats, bonus nights + more
Happy December!
Winter is (almost) here, and Upstate New York has officially entered its Hallmark era. Holiday markets are opening, ski mountains are coming online, and the first real flurries are moving through the Catskills and Hudson Valley. With the season shifting, we’re leaning fully into the cozy, fire-pit-and-snowshoe version of life up here.
This month’s Escape Club round-up brings together boutique hotels and short-term rentals suited for winter escapes — think custom stone hot tubs, backyard ice rinks, wood-burning fireplaces, and quick drives to the mountains. Promos range from free nights to generous midweek discounts, making it an especially good moment to plan a pre- or post-holiday getaway.
A quick note before we dive in: we’re running a Cyber Monday special — 20% off annual Escape Club subscriptions, today only.
In addition to our monthly travel deals, paid members now receive a new Wednesday newsletter every week, alternating between real estate features from Hannah and travel/design stories from me. If you’ve been thinking about joining (or gifting a subscription), this is the best price of the year.
Your subscriptions fuel this newsletter and our small, woman-owned and run business — thank you for being here! Redeem below 🎁👇
Stay warm, and happy holidays!
- Erin + the Escape Brooklyn team
Catskills Cloud House: Walkable Home with Private Ice Rink in Phoenicia, NY
The Stay | Set within walking distance of Phoenicia’s main street, Catskills Cloud House offers a modern, easygoing base for winter. High ceilings, expansive windows, and an open living area anchor the home, while three bedrooms provide space for groups, families, and pets. In winter, the backyard transforms into an ice rink, and a chiminea keeps the space warm enough for lingering outdoors between loops on the ice. The deck and fire pit remain steady gathering spots on cold evenings. Walkable to Phoenicia’s main street, the house sits close to coffee, restaurants, and local shops, creating a flexible base for a winter mountain escape.
Highlights | Seasonal backyard ice skating rink | Fire pit and chiminea | Pet-friendly accommodations | Chef’s kitchen | Walkable from town center | Proximity to skiing
The Deal | This month, Escape Club members can get a free third night added onto any two-night stay at Catskills Cloud House.
The Area | Phoenicia sits at the base of the Northern Catskills, where trails lead to sweeping overlooks and quiet forest routes suited for winter hiking and snowshoeing. In town, restaurants, cafes, and shops mix with a relaxed, small-town energy, creating an easy hub for wandering, coffee breaks, and time between outings. Check out the Escape Brooklyn Guide to Phoenicia for area recommendations.
Nearby | Skiing at Belleayre or Hunter Mountain | Elevated comfort food at Phoenicia Diner | Antique shopping at Phoenicia Arts and Antiques | Snowshoeing the Tanbark Loop (rentals available at the Catskill Visitor Center) | Dinner and drinks at The Pines
The Henderson: Maximalist Historic Escape in Hankins, NY
The Stay | Along Hankins Creek in the Western Catskills, The Henderson blends historic character with practical winter comforts. The restored 1860s Victorian has a living room centered on a wood-burning stove, followed by a chef’s kitchen with space for cooking and gathering. The dining room’s long table accommodates meals that can stretch into the evening, while the main-floor bathroom features a clawfoot tub tucked behind French doors that look onto the grounds. Outside, a heated stone hot tub and two fire pits provide quiet spots to bundle up around, and the surrounding landscape offers a sense of privacy.
Highlights | Moody Victorian interiors | Wood-burning stove | Large dining space for shared meals | Two outdoor fire pits | Custom stone hot tub | Clawfoot soaking tubs
The Deal | During the month of December, Escape Club members can take 10% off any stay at The Henderson.
The Area | Hankins sits in the Upper Delaware River Valley, surrounded by rolling countryside and towns with lively main streets. The nearby towns of Narrowsburg and Callicoon offer cafes, shops, and seasonal dining, while the river and surrounding hills create a scenic backdrop for winter walks or unhurried weekend drives. For a closer look at local favorites, see the Escape Brooklyn Guides to Callicoon and Narrowsburg.
Nearby | Snowy hikes on the Tusten Mountain Trail | Dinner at The Cochecton Fire Station | Vintage shopping at Tinker and Nidge and Moonriver Interiors | Coffee and breakfast at The Tusten Cup | Wine and tapas at Callicoon Wine Merchant
Seminary Hill: Michelin-Key Hotel, Restaurant, and Cidery in Callicoon, NY
The Stay | Seminary Hill takes on a quiet winter charm, with cozy interiors, carefully considered design, and seasonal touches woven throughout the property’s rooms and common spaces. The Boarding House, recognized with Michelin Keys in 2024 and 2025, offers individually designed rooms with kitchenettes, clawfoot tubs, and generous lounge spaces, along with shared areas like the Parlour Library for reading and board games. At the Tasting Room, indoor seating centers seasonal dishes made with local ingredients, while outdoor fire pits create a quiet place to sip cider and look out over the orchard.
Highlights | On-site restaurant and cidery | Cozy shared spaces | Pet-friendly accommodations | Complimentary breakfasts | Curated experiences
The Deal | This winter, Seminary Hill offers The Wintering Experience, a stay designed for rest and reflection. Guests receive a copy of Wintering: The Power of Rest and Retreat in Difficult Times by Katherine May, a premium travel journal, and guided prompts for reflection. In-room meal kits from the Tasting Room are included, and guests get 10% off provisions at The Callicoon Pantry to round out the retreat. Escape Club members can take 25% off Wintering Experience weekend stays in January and February.
The Area | Seminary Hill sits just outside the historic hamlet of Callicoon, where the walkable main street along the Delaware River offers galleries, shops, and restaurants that feel especially welcoming on colder days. For more local favorites, explore the Escape Brooklyn Guide to Seminary Hill.
Nearby | Dinner and cocktails at Black Walnut | Catch a movie at the historic Callicoon Theater | Main Street shopping at Lee Hartwell Antiques, Litt Home & Book, and Spruce Home Goods | Visit nearby North Branch North Branch Cider Mill, Homestedt Antique Barn, Catskills Vintage Art, and the North Branch Inn Restaurant
Two Good Cabins: Dual Lakefront Getaways in Roscoe, NY
The Stay | With colder days moving through the Catskills, Two Good Cabins offers a quiet, wood-clad retreat on the shores of Lake Muskoday. The chalet-style main cabin leans into its natural materials, with paneled interiors and a stone wood-burning fireplace that anchors unhurried mornings and long evenings by the fire. Across a short outdoor walkway, the studio guest cabin provides its own sense of refuge, complete with a wood-burning fireplace, kitchenette, and full bath. Outside, a lakeside fire pit sits at the edge of the property, offering a quiet place to gather with wide views of the water and surrounding woods.
Highlights | Wood-burning fireplaces in both cabins | Lakeside fire pit | Cozy, classic cabin interiors | Dining space for shared meals | Private lake frontage
The Deal | Escape Club members can take $200 off all stays through the end of 2025.
The Area | Roscoe offers a small-town main street with an easygoing pace. The surrounding forests and nearby trails invite winter walks and quiet time outdoors, while the town provides morning coffee, provisions, and a few favorite stops. For more local recommendations, see the Escape Brooklyn Guide to Roscoe.
Nearby | Winter tours of Buck Brook Alpacas | Provisions from Sullivan Sundries | Vintage shopping at Taylor + Ace | Shopping for vintage and new books at The Hound Books | Dinner and drinks at The Junction
The Mill Houses: Five Unique Homes in Livingston Manor, NY
The Stay | A short walk from Livingston Manor’s main street, The Mill Houses offer a winter-ready group of five individually designed homes set among evergreens and quiet, snowy woods. Interiors lean into cold-weather comfort, from Scandi-inspired minimalism to vintage country warmth, with wide-plank floors, birch plywood details, and clawfoot tubs that feel especially inviting when the temperature drops. Spend evenings at the shared fire pits, where groups gather under blankets, or onto porches and patios that stay cozy with layered textures and soft light — an easy home base for solo travelers, couples, or groups who want both village walkability and a calm retreat after a day in the cold.
Highlights | Unique interiors in each house | Shared fire pits | Walkable from Livingston Manor’s main street | Full kitchens in each house | Select houses with soaking tubs, fireplaces, and covered porches
The Deal | Through December, Escape Club Members can take 25% off all midweek stays of two or more nights.
The Area | Livingston Manor offers a walkable mix of cafés, shops, and small-town charm framed by winter woods. From the Mill Houses, it’s a quick stroll to breakfast and dinner spots, local boutiques, and seasonal happenings, while the surrounding mountains shift into a landscape of snow-dusted trails and quiet winter walks. For more local favorites, see the Escape Brooklyn Guide to Livingston Manor.
Nearby | Contemporary artwork at Catskill Art Space | Breakfast, lunch, and provisions at Main Street Farm | Shopping at Corners, Old Souls, Homestedt and nest | Dinner and drinks at Stumble Out and Threshold
The Moon Cabin: Cozy Log Cabin Retreat in Windham, NY
The Stay | On 2.5 private acres near Windham Mountain, The Moon Cabin shines during the winter. Vaulted ceilings and exposed beams frame a living area anchored by a wood-burning fireplace, with reading nooks and soft seating for curling up after a day outdoors. Outside, a wraparound deck and fire pit offer a quiet place to unwind under star-filled skies. Every corner of the cabin emphasizes warmth and comfort, from the Jacuzzi bathtub to the hand-hewn log details, making it an ideal retreat for ski season or snowshoeing in the surrounding woods.
Highlights | Wood-burning fireplace | Fire pit | Handcrafted log build | Classic cabin feel | Bordered by state-protected land | Jacuzzi soaking tub | Proximity to skiing
The Deal | Escape Club members can take 20% off any midweek stay booked through January.
The Area | Windham sits in the Northern Catskills, where early snow transforms the forests and peaks into a winter playground. The cabin is a short drive to Windham Mountain (with Hunter just a bit further) for downhill runs, while neighboring NYS-protected lands offer miles of trails for snowshoeing, winter hiking, and quiet walks through snow-dusted woods. For a closer look at local favorites, see the Escape Brooklyn Guide to Windham.
Nearby | Skiing at Windham and Hunter Mountain | Dinner and cocktails at Matilda | Breakfast at Fellow Mountain Cafe | Coffee and provisions from Paracasa | Spa treatments at The Windham Spa | Snowshoeing and winter hikes through the surrounding state-protected land