New England

10 New England Summer Vacations You Need to Book NOW!

To enjoy these prime New England resorts in summer or fall, it’s best to book your stay early. As in, right now.

By Steve Jermanok

Feb 05 2018


Beachmere’s front-row seat to the Maine coast keeps guests coming back year after year.

Photo Credit : courtesy of Beachmere Inn

10 New England Summer Vacations to Book NOW!

Beachmere Inn | Ogunquit, Maine

There are three reasons why the Beachmere continues to sell out summer after summer: location, location, location. A small gate at the far end of the inn’s sprawling lawn opens onto to the famous mile-long cliff walk they call the Marginal Way. Turn left, and you can stroll downhill to the main beach, stores, and restaurants in Ogunquit. Turn right, and discover even more breathtaking vistas of the jagged coastline and vast Atlantic. Keep going, and soon you’re in the compact neighborhood of Perkins Cove, where you can shop for painted lobster buoys and grab that requisite lobster roll at Barnacle Billy’s.

Beachmere’s front-row seat to the Maine coast keeps guests coming back year after year.
Photo Credit : courtesy of Beachmere Inn

BOOKING IT: “Many of our guests book at least a year in advance,” says innkeeper Sarah Diment. You can book one-week minimums for summer until April 1, and three-night minimums after April 1.

West Street Hotel | Bar Harbor, Maine 

After a day of hiking, biking, or sea kayaking in Acadia National Park, there’s arguably no better place to unwind than the welcoming West Street Hotel in Bar Harbor. Take in the mesmerizing seascape from your balcony, overlooking Bar Island and Sheep Porcupine Island and all the boats in between. You can head to the rooftop pool for an energizing dip; you also have the option to swim at the nearby Bar Harbor Club, whose Olympic-size pool is situated right on the edge of the ocean. The hotel is within easy walking distance of all the restaurants in town, so go ahead: Sample the zesty grilled fish tacos at Side Street Cafe, the blueberry pancakes at 2 Cats, and the heavenly black raspberry ice cream at Ben & Bill’s Chocolate Emporium.

BOOKING IT:To ensure you have your desired room come vacation season, the best time to book is winter or early spring. Minimum stays apply at peak times, such as summer weekends.

The Lodge on the Cove | Kennebunkport, Maine

Positioned for a 15-minute walk to the restaurants and shops of Dock Square and a 15-minute bike ride to Kennebunk Beach, the Lodge on the Cove is well situated to entertain the whole family. And it does so with gusto, offering food service at the outdoor pool; complimentary beach chairs, towels, and beach cruisers; nightly bonfires with s’mores; kayak and rowboat rentals at nearby Kennebunk Marina; lawn games; Saturday morning crafts; and movies in the clubhouse (with popcorn!). Four buildings house 30 spacious rooms, many of which are easy to connect for those making a multigenerational trip.

BOOKING IT:The property is open seasonally, May through October, and it’s recommended that guests book four to six months in advance, especially if seeking connecting double queen/king rooms. During the summer, there’s a two-night minimum on weekends, and a three-night minimum over holidays.

Winvian Farm | Morris, Connecticut

Winvian’s private cottages are awash with luxury touches.
Photo Credit : Courtesy of Winvian Farm

It was 2006 when the Smith family decided to transform their 113-acre estate in Litchfield Hills into one of New England’s most unique luxury resorts, hiring more than a dozen architects to create “cottages” nestled into the meadows, ponds, and rolling farmland surrounding the c. 1775 main house. These 18 custom structures are one-of-a-kind architectural gems that range from the Helicopter Cottage, which boasts a bar and entertainment center inside a fully restored 1968 helicopter, to the Treehouse Cottage, a two-story structure situated 32 feet off the ground, atop a tree. When not admiring the cottages, you can stroll through the wildflowers to a pond where great blue herons take flight or opt for a longer hike in the surrounding White Memorial Foundation, a 4,000-acre wildlife sanctuary. Afterward, treat yourself to a massage at the spa or a swim in the pool. Winvian is also a Relais & Chateaux property (as you’ll soon realize at dinner, a four-course feast), and it’s no surprise that it books out all cottages and the grounds for weddings in summer.

The spa house at Winvian Farm.
Photo Credit : courtesy of Winvian Farm

BOOKING IT:Holiday weekends (Memorial Day, Fourth of July, Labor Day) are booked as far as six months in advance. Of Winivan’s 18 cottages, the Greenhouse, the Camping Cottage, and the Artist Cottage are the most popular in summer and book six months out. A two-night minimum is required on weekends.

Cliffside Inn | Newport, Rhode Island

A short stroll from the Cliffside Inn is all you’ll need to understand the allure of this in-demand property. Within minutes you’ll access Newport’s famed Cliff Walk, a 3½-mile gem of a trail perched above the Atlantic and offering views of the sloping lawns and backsides of those summer “cottages” the Vanderbilts, Whitneys, and Astors built at the turn of the 20th century. But first you have to leave the cozy confines of this c. 1876 Victorian home. Each of the 13 guest rooms and three suites is distinctive; the Garden Suite, for example, is a duplex with its own private garden, a double Jacuzzi, two fireplaces (in the bathroom and the bedroom), and Peruvian limestone tiles that are heated so your tootsies won’t get cold on that long walk from bath to bed.

BOOKING IT:If you’re looking for a specific room in summer or fall, you’ll have to book in winter. There’s also a three-night minimum on weekends in summer, and a two-night minimum on weekdays.

Ale House Inn | Portsmouth, New Hampshire

With an up-and-coming food scene (including several chefs nominated for the prestigious James Beard Award) and one of the nation’s best collections of Georgian and Federal architecture, Portsmouth is a popular weekend getaway in the warmer months. The problem is the lack of available lodging near the center of town, with its collection of 40 antique buildings at Strawbery Banke and boutique shops, restaurants, and microbreweries near the waterfront. That’s the reason why the 10 rooms of the Ale House Inn, located on the third floor of a circa-1880 building on Bow Street, are always in high demand. One of the first Lark Hotels properties to debut (the company also manages the Hotel Portsmouth, on the other end of town), the Ale House Inn has the look of a cruise ship hallway. Plop your bags down in the light-filled rooms and grab your complimentary growler. Then make your way over to the Portsmouth Brewery for a taste of one of its signature brews, the Surrender to the Flow IPA. That will whet your appetite for the selection of New Hampshire oysters, harissa-rubbed grilled shrimp, and fries cooked in duck fat found at the Franklin. Work off dinner with a stroll across Memorial Bridge into Maine.

Ale House’s main lobby.
Photo Credit : courtesy of Ale House Inn

BOOKING IT:Rooms are booked as far as six months in advance for the summer months. Memorial Day weekend and July Fourth are particularly busy and may require further planning. A two-night minimum is required during peak summer months.

Land’s End Inn | Provincetown, Massachusetts

Considering that the Land’s End Inn offers a mere 18 rooms, most with ocean views, a few steps from the Provincetown breakwater and within easy walking distance of restaurants, shops, and bars, it’s easy to understand why this place books up months in advance for summer. A favorite room for romantics is the Moroccan Tower, furnished with assorted bric-a-brac from India and the Middle East, while the Library Room has a wraparound balcony, the ideal spot to sit with a stack of books and while away the hours. The inn also has a pet-friendly policy, enticing dog owners to make the trip to the tip of Cape Cod.

BOOKING IT:Most of the inn’s bookings for summer tend to be made January through March. There’s generally a four- or five-night minimum over weekends in July and August.

Rabbit Hill Inn | Waterford, Vermont

There’s no better place to rekindle romance than a stay at Vermont’s Rabbit Hill Inn. The 19-room country inn features eight “luxury” rooms, all equipped with a hot tub for two and a wood-burning fireplace. Then there’s the gourmet cuisine, defined as “pasture to plate,” featuring locally raised meats and produce. Opt for the inn’s two-night romance package, and you’ll enjoy sparkling wine and fine chocolates in your room upon arrival and an intimate three-course dinner (this is in addition to the standard full candlelit breakfast, and afternoon tea and pastries). There’s also the opportunity for an in-room massage.

BOOKING IT:Innkeeper Leslie Mulcahy notes that peak fall season (the last week of September through second week of October) books about a year in advance. “Quite often, when guests are here they book for the following year,” she says. If your travel dates are flexible, there are still some openings available for autumn 2018. Note that there are two-night minimums on weekends in fall.

Hotel Salem | Salem, Massachusetts

Located less than 20 miles northeast of Boston, the historic hamlet of Salem may be best known as the place where 20 innocent people were put to death during the witch trials of 1692–1693. Salem remembers its infamous past each October by staging a 24-day event called Haunted Happenings, which—with its numerous haunted houses, psychic fairs, and costume parades—helps make this city the “Halloween Capital of the World.” Good luck trying to snag one of the 11 rooms at the Merchant, a popular boutique hotel in the former 18th-century home of shipping merchant Joshua Ward. You might have a better chance at Hotel Salem, which made its debut last November in a former upscale department store called Newmarket: It offers 44 spacious rooms, Salem’s lone rooftop bar, and a restaurant downstairs in the basement simply called Counter.

Hotel Salem’s boutique rooms go quickly for the Halloween season.
Photo Credit : courtesy of Hotel Salem

BOOKING IT: While October is Salem’s busiest tourism season, the seaside town is bustling all summer long. Two-night minimums are required for summer stays, and the hotel’s most coveted room, the Lark Suite (two floors, lofted), is usually the first to go.

Union Street Inn | Nantucket, Massachusetts

Why has the Union Street Inn received so many rave reviews from guests and national press? One word: expertise. Ken Withrow was the manager of Ian Schrager’s Royalton Hotel in Manhattan; his wife, Deb, has a background in retail management at Henri Bendel and Fiorucci. Deb is also a talented chef, as you’ll soon find out at the inn’s sumptuous breakfast, which more than likely will feature her signature challah French toast topped with blueberries and/or strawberries and served with Vermont maple syrup. Less than a five-minute walk from the ferry, near the restaurants and shops on Main Street, Union Street Inn offers just 12 rooms, the reason why it’s a challenge to book in the summer months.

BOOKING IT:Ken suggests calling in March or April for the summer high season, but you might still find vacancies in May and June if you’re flexible with dates.