New England

10 Merry New England Inns for the Holidays

Get into the spirit of the season at these jolly New England overnights.

By Yankee Magazine

Oct 26 2022


Anchorage by the Sea, Maine

Photo Credit : Courtesy of Anchorage by the Sea
In the 2022 holiday feature “The Merriest Inn of All,”Yankee travel editor Kim Knox Beckius details how three remarkable friends have been bringing yuletide magic to Vermont’s Wilburton Inn for more than a decade. The result of their annual efforts is a twinkling, evergreen extravaganza that puts this Manchester, Vermont, inn on the “Merry New England” map. Here, Kim shares nine additional picks for New England inns with a similar dedication to creating the ultimate festive getaway.

9 More Merry New England Inns for the Holidays

Anchorage by the SeaOgunquit, ME

Ogunquit’s shops and annual Christmas by the Sea festivities are within walking distance of this waterfront resort, and longtime owners the Ramsey family take their location in the midst of all that merriment very seriously. Up go white lights and swags of greenery. Seasonal cocktails (sometimes naughty, sometimes nice) await at Surf Point 360. And while this is a large property, several of its buildings feel distinctly inn-like—as does the warmth of the employees, many of whom have greeted returning families for over 30 years.

Harraseeket InnFreeport, ME

The real fun isn’t just bringing a special ornament to hang on the Community Tree in the inn’s drawing room; it’s returning here, years from now, to search for (and likely find) your contribution. But this sweet tradition isn’t the only reason to make a holiday escape to this 94-room property, a Freeport mainstay ever since it was built around a 19th-century Greek Revival house in 1984. You’ll never forget being in town during the annual 10-day Sparkle Celebration: Where else can you converse with Freeport’s famous talking Christmas tree and shop all night at L.L. Bean?

Inn at Ellis RiverJackson, NH

With romantic amenities such as in-room fireplaces and jetted tubs for two, this country inn is particularly inviting when the snow flies. While innkeepers John and Mary Kendzierski close down to focus on family during the two weeks before Christmas, they load up the first half of December with holiday fun for guests. Reserve afternoon tea beside a decked-out tree, wear your ugliest Christmas sweater to the cookie swap and dramatic reading of A Christmas Carol, or time your visit for the region’s annual Inn-to-Inn Holiday Cookie Tour, when John and assistant innkeeper Christine Baumann bake 1,200-plus festive treats.

Inn at Pleasant Lake, New Hampshire

Inn at Pleasant LakeNew London, NH

The view of Mount Kearsarge across the water has been a gift to this inn’s guests for more than 150 years. A fine dinner by Christmas-tree-light at the on-site restaurant Oak & Grain is an experience to cherish, too—perhaps even more than anything you could wrap in pretty paper. To fully embrace the holiday spirit, come right after Christmas, when the inn’s vintage barn becomes a Gallery of Trees, all decorated by local businesses. You have until New Year’s Eve to vote for your favorite, and if you make a donation too, you can feel good knowing the winner will funnel all funds to a worthy local cause.

The Red Lion Inn, Massachusetts

The Red Lion InnStockbridge, MA

When Norman Rockwell’s famous Stockbridge Main Street at Christmas was published in McCall’s in 1967, editors said of the painting: “Wherever you happen to hail from … we hope you will have, for a moment, the feeling of coming home for Christmas.” That’s still the emotion that this Main Street icon strives to elicit from its guests today. More than 30 Christmas trees and 700 feet of pine garland dress up the historic inn, and when you open the front door to the enormous Christmas tree and fireplace’s toasty warmth, it’s as if you’re stepping into a memory, even if it’s your first visit. Time your getaway to coincide with the town’s annual Stockbridge Main Street at Christmas celebration, held the first weekend in December.

Weekapaug InnWesterly, RI

A traditional Italian Feast of the Fishes is a Christmas Eve standby at this waterside historic inn. Slip into Hunter boots from the Hunter Borrowing Closet for a walk in any weather, warm up with a hot drink by a snap-crackling wood fire, make s’mores by the fire pit outdoors, and tuck yourself in at night just the way (or better than) you would at home, with your pooch slumbering in an Annie Selke–designed dog bed by your side.

Westbrook InnWestbrook, CT

Merry is the prevailing spirit throughout a month of festivities in and around this Victorian B&B with contemporary polish. Head out for a community tree lighting, artisan bazaars, and Essex Steam Train’s North Pole Express rides; stay in to enjoy sweets and savories at the inn’s ticketed high Christmas tea. The parlor tree is adorned with pink blossoms, dainty teacups, and light-reflecting hotel keys; the great room’s tree decked out in peacock blue and gold. Wake up here Christmas morning, and you’ll find Santa’s left you a locally made gift.

The Captain’s House Inn Chatham, MA

At this classic Cape Cod ship captain’s home turned bustling inn, lovely greenery and a sparkling tree make the atmosphere merry for holiday high tea. If you’re lucky, you’ll feel like you’re in a snow globe with flurries flying outside floor-to-ceiling windows. Displays of seasonal scones, sandwiches, and sweets are presented daily from noon to 3 p.m., and even if you’re only in Chatham for a day of gift-hunting along Main Street, you should carve out time for this tradition (make reservations at least 24 hours in advance). Rooms with fireplaces and four-poster beds may tempt you to stay over, though, and make the adults-only Captain’s House Inn your home base for Chatham’s Christmas by the Sea Stroll, always the second weekend in December, or the town’s arts-centric First Night celebration on New Year’s Eve.

Castle Hill Inn Newport, RI

Unmatched for the elegance of its holiday decor and the coziness of its many wood-burning fireplaces, this oceanside icon retains its 19th-century grace while offering distinctly 21st-century enticements. Make reservations early for sumptuous, multi-course holiday meals and rooms in the mansion or by the sea. For the second year, the inn’s Chalet Lawn will be transformed into a pop-up Christmas tree farm during the first week of December, and there’ll be complimentary hot cocoa and cider, photo ops in the “Letter to Santa” workshop, and the feel-good opportunity to support the James L. Maher Center’s work on behalf of people with intellectual and developmental disabilities through your tree or wreath purchase. Also back this year: Gather your group of up to six and enjoy “S’more Holiday Cheer” by an outdoor fire pit. Your reservation even includes three snuggly fleece blankets to take home.