Is there any real surprise that the classic Vermont village of Woodstock is regularly praised as one of America’s prettiest towns? Between the bucolic landscape, a downtown that seems right out of central casting, and one of the prettiest covered bridges in the entire country, it more than lives up to the billing. Which may lead you to think that finding a place to stay in this quintessential New England town is tricky. Not so: The Woodstock region is chock-full of options. Ready for a visit? Read on for our list of favorite Woodstock, Vermont, hotels and inns.

Ian Aldrich

And before you hit the road, be sure to check out Yankee’s list of best restaurants in Woodstock, Vermont, and our favorite things to do in town. In search of a complete itinerary? Don’t miss our Woodstock weekend planner.

Woodstock, Vermont | Hotels & Inns Guide

Aimee Tucker

Crossing the threshold at Woodstock’s best address is like stepping into a sumptuous country home. Many guest rooms feature wood-burning fireplaces; all are distinctively furnished. Local ingredients enrich the menus at the Red Rooster, the inn’s light-filled main dining room, and at the snug, wood-paneled Richardson’s Tavern. The resort offers golf, ski, and spa packages, plus activities ranging from fly-fishing to falconry. Woodstock’s shops, restaurants, and town green are at the inn’s doorstep. Named a 2017 Yankee Editors’ Pick for “Best Upscale Inn.”

Courtesy of 506 On the River Inn

Just a few miles from the center of Woodstock, along the scenic Ottauquechee River, 506 On the River Inn combines the best features of a small resort with those of an intimate inn. At guests’ disposal are river-facing rooms and suites with balconies and rocking chairs, an antiques-filled bistro and bar, a game area for young adults, a toddler playroom, an indoor pool and sauna, and a sweeping lawn dotted with lounge chairs, tiki lamps, and fire pits for evening s’mores. Named a 2017 Yankee Editors’ Pick for “Best Boutique Inn.”

Courtesy of the Ardmore

Charlotte Hollingsworth, a former bookstore manager, has named each of the five rooms here for a Vermont author or illustrator, fitted with appropriate volumes. (The Archer Mayor room is quite cozy.) Check out the well-stocked downstairs library and a many-windowed sunroom with rockers for reading. Breakfast is a multicourse delight. Named a 2013 Yankee Editors’ Pick for “Best Reader’s Retreat.”

Courtesy of the Jackson House Inn

Romance is the hallmark of this luxury lodging, from the elegant English gardens to imaginative two-course breakfasts. Cozy spots abound: Sink into a comfy seat in front of the main fireplace, or settle into a chair on the porch to enjoy offer sweeping views of the Vermont landscape. Named a 2016 Yankee Editors’ Pick for “Best Couples Retreat.”

Three-course breakfasts, a primo downtown location, and an interior that oozes old-world charm all play starring roles at this nine-room historic inn. Choose from an array of special packages, including the “Pampering” (chocolate truffles and massages), “I Love You” (roses, chocolates, and champagne) and “Simon Pearce” (dinner dates at the glassmaker’s acclaimed restaurant).

The story of this establishment begins in 1963, when the Shire was built as a 12-room motel. Today, this riverside hotel offers an array of guest options, from bunk rooms to expansive suites. The Riverhouse has room for up to eight guests, with two full bedrooms and two full baths.

Courtesy of the Woodbridge Inn

Situated atop the banks of the Ottauquechee River, the Woodbridge features five guest rooms. Amenities at this small B&B include full breakfasts, afternoon tea, and private baths. Be sure to say hello to the inn’s friendly and furry greeters, a pair of shih tzus named Max and Harmony.

Do you have any favorite Woodstock, Vermont, hotels and inns? Let us know!