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Review: Woodstock Inn & Resort

The town’s original winter-tourism destination has maintained every bit of its Norman Rockwell-worthy nostalgia
Readers Choice Awards 2017, 2018, 2019, 2020, 2021, 2022, 2023, 2024 Gold List 2025
  • Woodstock Inn & Resort, Vermont
Courtesy Woodstock Inn & Resort

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Woodstock Inn & Resort, Vermont
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Amenities

Rooms

142

Why book?

In a rural Vermont village, the Woodstock Inn & Resort delivers five-star service, modern amenities, and activities that harken back to when family vacation revolved around board games, tennis court battles, and offline hikes and ski adventures.

Set the scene

These days, most hotel lobbies look like co-working spaces. The Woodstock Inn channels laidback living room vibes. A ruddy-cheeked family fresh off the ski slopes collapses on a couch by the colossal fireplace that anchors the inn’s sprawling lobby. Nearby, an older couple dressed in L.L. Bean lounge in oversized club chairs exchanging sections of the New York Times (yes, the real print version). Opposite them, a younger couple—him in a Faherty flannel, her in the brand’s flannel dress— have abandoned their shoes and sip hot toddies as they play gin rummy. There isn’t a screen in sight. Around one corner, three girlfriends still in their Swix nordic apparel, are drinking cocktails and noshing on an artisanal cheese plate at the bar. Around another, a grandson and grandfather go head to head at a chess table in the quiet library.

The backstory

Established in 1793 as Richardson’s Tavern, a stagecoach inn servicing passengers traveling between Boston and Montreal, the name later changed to the Eagle Hotel after a local cabinet maker carved a golden eagle above the tavern’s entrance (the eagle emblem remains part of the inn’s brand identity today). In 1892, the humble hotel was replaced with the grand, Victorian-style Woodstock Inn, which quickly became known for its riotous winter parties and affluent crowd. Laurance S. Rockefeller was married in Woodstock as his wife, Mary Billings French, had long familial ties to the area. In the late 1960s, the philanthropic couple bought and completely rebuilt the inn from the ground up and invested millions in local land preservation. Since then, the resort has expanded four more times.

The rooms

Ever since the inn’s 142 rooms underwent a $6.5 million glow up in 2018, one of the top asks from guests has been to reveal the paint names so they can recreate the serene butter yellow and light aqua color scheme at home. Rooms are decorated with botanical prints, local art, and Vermont-crafted touches, such as cherry wood bed frames and Anichini sheets. Garden rooms face the south lawn while Woodstock rooms face the front of the inn, and the slightly more luxe Tavern wing rooms feature built-in bookshelves and a writing desk. Ten Collection rooms are decorated to reflect different Vermont-inspired themes. The Alpine, for instance, has vintage skis hanging from the walls, while the Angler showcases antique fly rods. Seven legacy suites, the inn’s top room category, pay homage to the people who helped shape Woodstock, including conservationist George P. Marsh and artist Arthur Wilder. Truly worthy of its namesake, the creme dela creme, three-room Laurance S. Rockefeller suite features custom, Federal-era furnishings, a steam shower and soaking tub, and a hand-painted, wrap-around mural depicting the bucolic Vermont countryside. Select rooms are pet-friendly and a handful of rooms can be configured to adjoin.

Food and drink

Kelly Way Gardens, the inn’s three-acre, farm-to-table project down the road, supplies the resort with more than 200 varieties of vegetables, 50 types of herbs and edible flowers, 75 kinds of berries and orchard fruits, plus honey from its bees. From June through September the gardens host multi-course dinners typically twice a week in a beautifully restored barn. You’ll want to book a few weeks in advance. The menu at the Red Rooster, the inn’s main restaurant, is a love letter to New England ingredients, right down to the Kedron Valley Stables sea salt-studded, maple whipped butter that comes with the house made Parker Rolls. If you can’t get a reservation, the bar offers about a half dozen Red Rooster dishes, plus excellent cocktails crafted from local spirits like Bar Hill Gin, which is featured in the exceptional negroni. The inn’s historic tavern has a roaring fire and a dinner menu of comfort foods like smoked chicken wings and pork schnitzel.

The spa On a cold winter day, there’s no place cozier than the inn’s Scandi-inspired spa. Wrap yourself in a fur throw and snuggle up in a lounger by the Shaker wood stoves in the great room. Or head out to the courtyard and warm yourself in the hot tub or sauna. The 10,000-square-foot space has ten treatment rooms on its second floor. Sore muscles will thank you for adding the muscle-melting CBD balm enhancement to your massage.

The neighborhood/area

The shire town of Woodstock, with its covered bridges and white-steepled churches, feels like the quintessential New England town, no matter the season you visit. Centrally located across from the town green, the inn is walking distance to the shops, galleries, and restaurants that line the two main thoroughfares, Central and Elm Streets. A public chalkboard still acts as a modern-day town crier broadcasting local news, and the 19th-century general store has shelves lined with hardware and gardening supplies, produce, beer and wine, and enough maple syrup to get you through winter. Between June and October the green hosts a farmer’s market with 30-some local purveyors. Tucked away down Mechanic Street, just a few steps from the inn, darling bar Au Comptoir is one the few spots in town that’s open on Mondays and serves gourmet small bites and excellent cocktails until 10pm. The inn’s athletic club, nordic center, and Robert Trent Jones, Sr.-designed golf course, as well as local ski area Saskadena Six, are all less than a 10-minute drive from the inn.

The service

Staff exude small-town pride and an all-star concierge team ensure you see everything the area has to offer. If you’ve mastered the 28 miles of trails at the inn’s nordic center the team will direct you to the trails at Mt. Peg. If you want to dine off-site, they can help secure reservations at Santé or the Prince & the Pauper. When you return to the inn, the team genuinely wants to know how your day was.

For families

The inn is a dream for families of all ages. Play lawn games like cornhole or giant Jenga on the lawn, rent cruiser bikes from the activity center, sign up for tennis or pickleball lessons. The south lawn features a fire pit for roasting S’mores. In winter, a retro game room keeps kids occupied with pinball, Scrabble, vintage video games, and more. The spa offers teen-specific therapies. Throughout the year, the inn offers kid-focused pop-up experiences like indoor mini golf, karaoke, glow dance parties, and homespun cotton candy hour. At Kelly Way Gardens, family fun tours include free tastings of locally-grown ingredients. The four-bedroom Morgan House, a historic home across from the main inn, is a nice option for families.

Eco effort

Around 75 percent of all trees and shrubs planted at the resort properties are native to New England, with an emphasis on plantings that support pollinators, and only electric lawn mowing and leaf blowing equipment is used on property. The Kelly Way Gardens are Vermont Certified Organic and engage in a composting program. The spa is LEED-certified and guests will find two electric car charging stations. In spring 2025, the resort will convert 14 acres of resort-owned hay fields into forested riparian buffer, planting around 5,600 trees along the Ottauquechee River to strengthen the riverbanks against flooding.

Accessibility

The property is ADA friendly with a ramp at the front of the inn that leads to the lobby and elevators that access the guest rooms and spa. The Woodstock Country Club also has elevators and the pools at the inn and Athletic Club have ADA-compliant lifts. A selection of both the king and double queen category rooms are ADA accessible and feature roll-in showers. Vermont Adaptive Ski & Sports is a local organization that offers year-round programs and equipment and Saskadena Six and Mt. Peg both have adaptive-accessible mountain bike trails.

Anything left to mention?

Admission to the Billings Farm & Museum, just a half-mile away, is complimentary for inn guests; visitors can watch the animals get milked every day at 3pm. History buffs take note: two of Paul Revere’s original cast bells are located on property. A complimentary shuttle transfers guests between the resort facilities. Check the inn’s website for themed packages that offer incredible savings, like unlimited access to the nordic center and local ski area.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

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