I Just Found 8 Airbnbs That Look Straight Out of ‘The Holiday’ (All Within Driving Distance of NYC)

• Sleeps: 10 
• Rate: from $865/night
• Why We Love It: 250-acre property with private stables, hot tub and firepit, Peloton bike, fishing pond, board games, just minutes from Stamford’s cafés and shops

If Iris’s cottage had been listed on Airbnb in the early 2000s, I presume Amanda would’ve been angling for something like this. The stone façade and sprawling landscape deliver secluded countryside romance, but the interiors are brighter, airier and more polished than Iris’s snug hideaway. The living room’s massive fieldstone fireplace keeps the rustic heart, while crisp white walls and layered neutrals give it an Amanda-approved upgrade. The kitchen also leans farmhouse but elevated: patterned tile, stainless steel appliances and floating shelves instead of cluttered cupboards. Upstairs, wood-paneled bedrooms tuck under pitched ceilings, warmed by quilts and fireplaces that feel straight out of Surrey—only sleeker, more curated. And with 250 acres to roam, horses grazing in the fields, and a private pond for fishing, it has all the lived-in charm Iris’s home promised, with just enough refinement for Amanda’s taste.

• Sleeps: 12
• Rate: from $1,216/night 
• Why We Love It: Scandinavian-inspired design, 30-foot glass curtain wall with mountain views, spa-like bathroom with soaking tub and heated floors, glass-wrapped office, private gym, EV charger

Here, meet the European twin of Amanda’s San Marino estate. The interiors strike that balance she craves: minimalist lines and grand scale, softened by organic materials and a neutral palette that feels equal parts Catskills and Côte d’Azur. The living room’s 30-foot glass wall makes the forest the artwork, while pale oak floors, cream sofas, and sculptural lighting keep the space polished without feeling cold. The kitchen channels her signature style—expansive and high-end—yet the wood cabinetry and open shelving lend a touch of rustic restraint. Bedrooms are pared back but inviting, with platform beds, asymmetrical windows, and warm textures that read chic rather than stark. Add in a glass-wrapped office and private gym, and you’ve got Amanda’s sleek California sensibility, infused with the soul of a European retreat.

• Sleeps: 5
• Rate: from $415; $365/night 
• Why We Love It: 2 hours drive from NYC, window-pane walls, central fireplace, game room with ping pong + pinball, EV charger, dog-friendly, meadows feel like a private sanctuary

This barn is undeniably Iris (but it’s just two hours outside of NYC). The bones are all there: shiplap walls, exposed beams wood-burning hearth, and French doors that open to rolling meadows. But instead of a snug, dim space, the interiors lean bright and airy—window sashes divide the rooms while keeping everything open and full of light. The fireplace anchors the great room much like Iris’s stone hearth, but here it’s a mid-century suspended design that feels sculptural and fresh. Bedrooms carry her cozy DNA too, with wood-paneled walls and quilts, but the lofted layout and built-in shelving add a modern utility. Not to mention that this barn takes it a step further than Iris’s home: a game room with a pinball machine, a kitchen prepped with butcher-block counters and stainless steel and an EV charger for anyone arriving in a Tesla.

• Sleeps: 8
• Rate: from $1,691/night 
• Why We Love It: 14 secluded acres just minutes from Millbrook village, heated saline pool with bluestone patio, wisteria-covered pergola dining area, private gym with Peloton, guest house suite, two ponds with walking trails and kayaking

This is another property that mimics Amanda’s design (if she traded Brentwood for Millbrook). The palette is sharp and restrained—white walls, black-framed windows, pale oak floors—giving that gallery-like backdrop for sleek furniture and statement lighting. The kitchen nails her style with its dark slab cabinetry and oversized stone island that feels equal parts functional and cinematic. In the living room, sculptural accents and low-slung seating echo her LA mansion’s curated, design-first approach. Even the bedrooms lean Amanda: tailored lines, crisp whites, and a sense of order that reads modern rather than cozy. Outside, the saline pool, bluestone terrace, and firepit keep the vibe firmly in her camp—glamorous, self-contained, and just indulgent enough to feel like a set.

• Sleeps: 6
• Rate: from $508/night 
• Why We Love It: Salvaged barn frame turned light-filled treehouse, soaring great room with exposed beams, chef’s kitchen, private trails on 5.5 acres, hot tub and sauna, babbling brook, and a detached “in-law treehouse” for extra space

Next up: A property that hits the sweet spot between Iris’s snug Surrey cottage and Amanda’s polished LA estate. You have the romance of timber beams, wide-plank floors and cozy nooks that feel handmade for quilts and story time—but the scale is pure modern barn fantasy. The soaring great room brings in Vermont’s winter light through double-height windows, while the stone-topped chef’s kitchen and bar seating make it easy to swap solitary cups of tea for a family feast. Bedrooms are tucked under sloped ceilings with just enough intimacy to channel Rosehill Cottage, only here there’s also a home theater loft for movie nights and a hot tub/sauna setup waiting outside. Add in private cross-country ski trails, a brook running the property’s length and Manchester’s shops and restaurants just 20 minutes away, and it has Iris’s cozy heart wrapped in Amanda’s ease of living—quintessential New England escapism for 2025.

• Sleeps: 6
• Rate: from $582/night 
• Why We Love It: Renovated farmhouse with Scandinavian touches, heated gunite pool, kitchen with Devol fixtures, sunroom wrapped in glass, ABC Carpet sectional, firepit and sweeping Hudson Valley views

My first thought when I saw this property? This is the set Nancy Meyers would dream up if she were doing a sequel of The Holiday in 2025. On one hand, it has Iris’s English coziness—beamed ceilings, a sunroom with floor-to-ceiling windows that catch the snowfall and tucked-away nooks made for curling up with tea and a novel. On the other, Amanda’s fingerprints are everywhere: a Devol-fitted chef’s kitchen with skylights, a Miele fridge and Bertazzoni range, a pristine home office that doubles as a guest room and a pool so cinematic it begs for striped umbrellas and Aperol spritzes. The bedrooms lean more Iris—simple quilts and softness layered into every corner—while the open lounge channels Amanda’s polished side with its sprawling ABC Carpet sectional. Bathrooms bring the two worlds together: a vintage porcelain tub meets marble sink and rainfall shower. Step outside and it’s all Hudson Valley romance—apple trees, perennials and a firepit with Adirondack chairs.

• Sleeps: 8
• Rate: from $532/night
• Why We Love It: Stone fireplace and beamed ceilings, hot tub, koi pond and firepit, game room with guitars and arcade, screened porch, and five private acres near Mount Snow

Tucked into five acres of Vermont forest, this chalet feels like Iris’s cottage translated for a big family gathering. The design still hits all her signatures—exposed beams, layered textures, a stone hearth at the center of it all—but everything is scaled up for 2025 living. Instead of one snug bedroom, you’ve got four (including a king suite with its own jacuzzi and screened porch). The cottage’s tiny kitchen is now a chef’s setup stocked with spices and olive oil, meant for actual feasts. And where Iris had one well-worn sofa, here you’ll find multiple fireside seating areas plus a game room tucked under the eaves with velvet armchairs, guitars, and wallpaper that feels equal parts nostalgic and playful. Outside, the hammock and koi pond keep the romance, only now you’ve also got a bubbling hot tub, a fire table, and five wooded acres to wander. It’s all the cozy heart of Iris’s cottage—just bigger, better, and ready for your whole crew.

• Sleeps: 6
• Rate: from $3,366/night
• Why We Love It: Infinity pool with hot tub, 100 acres of historic Vanderbilt farmland to roam, collectible modern furniture, soaring 36-foot glass wall, Scavolini kitchen and a location steeped in Gilded Age history

This carriage house may be historic on the outside, but step inside and it’s Amanda’s LA property reincarnated in the Hudson Valley. The interiors strike that same balance of loft-like scale and minimalist restraint: white walls, steel-framed windows and a soaring 36-foot glass curtain wall. The kitchen is all sleek Scavolini lines and polished surfaces—an almost one-to-one match with Amanda’s state-of-the-art setup—while the dining room flows effortlessly into the open layout. The furnishings are also straight out of her design playbook, from Breuer and Gio Ponti chairs to Saarinen and Philippe Starck accents—all softened by pale oak floors and sculptural lighting. Add in the infinity pool, tennis court and access to the Vanderbilt estate’s orchards, trails and old-growth forest, and it’s Amanda’s cinematic California life—just with Hudson River views and a historic pedigree.