Maine is beloved as a summer getaway for travelers from around the world, but it is drastically underrated as a fantastic wintertime destination. Charming coastal towns transform from their summer splendor into Dickensian Christmas wonderlands. The forests in the center of the state switch from hikers’ paradise to a cross-country skier’s dream. Maine’s hills and mountains make perhaps the greatest transformation: from endless rolling wilderness dotted with blueberry patches to a network of fantastic family-friendly ski resorts. Whatever your ideal winter vacation looks like, Maine likely has it.
01 of 09
Located at the base of Sugarloaf Mountain, the largest ski resort in the East, the Sugarloaf Mountain Hotel has something to offer every kind of traveler: outdoor sports enthusiasts, families with small children, even those on a romantic getaway. Room sizes range from a standard queen to a three-bedroom suite (the latter include a private hot tub and sauna), and all are decorated in an upscale rustic style, with warm colors and natural pine furniture. Beds are all Boyne luxury beds, complete with high thread count linens and Primaloft comforters.
An on-site gourmet restaurant, 45 North, offers guests upscale meal options, and the hotel is a close walk to several casual eateries. A health club with a sauna and steam room, a lobby fireplace (as well as fireplaces in many rooms), and a massive 30-person outdoor hot tub provide plenty of places to defrost after a day of outdoor sports.
And the outdoor sports options are impressive. Downhill skiers and snowboarders can enjoy 163 trails... serviced by 12 lifts (one of which is 150 feet from the hotel door; the rest are an easy walk away), as well as three terrain parks, a superpipe, and a snowboardcross course. Other outdoor options include 90 km of cross-country skiing/snowshoeing trails and an Olympic-sized ice skating rink, both nearby at the Sugarloaf Outdoor Center.
02 of 09
The Kennebunks are a summer playground for the rich and famous, including the Bush family, who own a nearby compound. Fewer people know that they’re equally wonderful to visit in the winter, when the port area of Kennebunkport becomes postcard-perfect with festive decorations for Christmas and Valentine’s Day. The Grace White Barn Inn, technically located in Kennebunk but just a short walk to Kennebunkport’s shopping, dining, and galleries, offers guests all of the town’s charm and luxury in one cozy package.
Each of the Inn’s 26 rooms, suites, and cottages is individually appointed with a combination of understated contemporary decor and antique touches. Pillowtop mattresses, luxury fabrics, and walk-in rain showers are found in all rooms, and many also include fireplaces and deep soaking tubs. A full-service on-site spa and the White Barn Restaurant, a Forbes 5 Star and AAA Five Diamond restaurant, complete the luxury experience.
03 of 09
The Wilson Lake Inn is a quaint throwback an era when roadside motor lodges were often quite lovely places to stay. It’s situated right on the edge of gorgeous Wilson Lake and offers gorgeous views of the lake and beautifully landscaped grounds from which to enjoy them. Rooms are simple but comfy, and range from basic hotel-style twin and queen rooms to full apartment-style suites with full kitchens. There’s no on-site restaurant, but the village of Wilton and nearby Farmington have lots of good takeout and dine-in options.
The Inn’s location in Wilton puts travelers just minutes from the small but sweet Titcomb Mountain, a family-focused mountain which offers both Nordic and downhill skiing and snowboarding for all levels. More serious skiers might prefer to head a half-hour away to the Black Mountain Ski Resort, with whom Wilson Lake Inn offers ski-and-stay package deals. This third-tallest mountain in Maine offers both simple and challenging terrain in a strikingly beautiful... middle-of-nowhere setting, with stunning natural views in every direction.
04 of 09
A recent renovation brought this historic hotel, formerly known as the Captain Daniel Stone Inn, to a whole new level of chic contemporary glory. Antique-style furnishings and sleek modern touches combined with rich blue, gold, and burgundy accents make the guest rooms feel simultaneously cozy and stylish. Bathrooms have marble countertops and tiled showers and include complimentary amenities from the posh William Roam line. Each room is outfitted with a Keurig coffeemaker.
House-baked pastries and quiches line the complimentary continental breakfast table daily, and should you decide to spend the day doing outdoor activities, you can make a reservation to use the hotel’s private sauna or hot tub. Coast Bar and Bistro offers on-site gourmet dining daily and live music on Thursday evenings. The Daniel is a convenient 15-minute drive to the flagship L.L. Bean store in Freeport, where winter is jam-packed with events, from sleigh rides to Santa meet-and-greets to free daily snowshoeing... lessons. It’s also minutes from Bowdoin College, which offers concerts and other performances regularly.Continue to 5 of 9 below.
05 of 09
Spread out in the large comfortable rooms at this resort which transforms from a summertime golfer’s paradise to a wintertime skier’s dream. Spend the day exploring the resort’s many miles of cross-country trails on ski or snowshoe or make the short drive to either the huge, all-levels Sunday River ski area or the cute, family-friendly Mt. Abrams to ski downhill. Less sports-inclined families can still enjoy the outdoors with weekend sleigh rides, ice skating, and even dog-sledding. At the end of the day, thaw out in the large heated outdoor pool or saunas.
On-site restaurants include plenty of options for kids — even picky ones — and the spa gives parents a place to escape for a bit. An arcade and game room is available, as well, which includes darts and a pool table. Multiple room types are available, from standard queens and kings to two- and three-bedroom suites, so all types of families can be easily accommodated. The decor is country-classic, and many rooms include a kitchenette:... a great amenity for even the shortest vacations with kids!
06 of 09
The elegant Meadowmere Resort has offered their special Romance Package to countless couples for over thirty years, and it remains popular. Guests who treat themselves to this package start with a wine and Cabot cheese plate upon their arrival, and enjoy a special meal at a local gourmet restaurant, a complimentary in-room breakfast basket, access to Meadowmere’s Roman Spa and other resort amenities, and an extra-late checkout time for bonus hours of canoodling.
Even without the package bonuses, the resort is a perfect place for a romantic getaway. Rooms and suites, each of which is uniquely decorated in an upscale coastal style, include touches like four-poster beds, in-room fireplaces, and jacuzzis. The Meadowmere is a short walk from the charming coastal Ogunquit Village and Perkins Cove, where guests can find food, shopping and other attractions.
07 of 09
The Rangeley Lakes region is one of breathtaking scenery in every direction: snow-capped peaks rising up between hundreds of tiny lakes and ponds, interspersed with charming tiny villages. Rangeley is the most iconic of these, and just at the end of the three-block stretch of Main Street, on the shore of Haley Pond, sits the Rangeley Inn. It’s a beautiful historic property in and of itself, with simple rooms decorated with a gentle country touch (think patchwork fabrics and soft floral wallpapers). As sweet as the rooms are, they’re not the highlight: the view of the pond and the surrounding mountains are.
Rangeley Inn is not just great for immediate location, though — its location at the heart of the region puts visitors within striking distance of all of the great winter activities nearby. Sugarloaf Mountain and Saddleback Ski Area are both close by. Snowmobiling, cross-country skiing and snowshoeing are all available, and once it’s cold enough for Haley Pond to freeze, it’s a... favorite local spot to go ice skating. After a day outside, come back to the Inn and enjoy hot cocoa by the fireplace or a rustic-chic dinner in the award-winning on-site restaurant.
08 of 09
This gorgeous coastal cottage is steeped in 125 years of Homer family history, which the hosts will happily tell you about over breakfasts of lobster omelets and French toast with homemade apple syrup. While you nosh, they’ll help you fashion a day’s plan, which will almost certainly include Acadia National Park, which surrounds the B&B. In the wintertime, the park is gorgeous for snowshoeing and hiking, and the nearby coastal villages are excited to welcome off-season guests, as well.
At the end of your day of exploring, return to the house and build a fire in the massive stone fireplace and warm up before retiring to your homey, antique-filled room. It’s the tiny touches that put The Birches above the rest, though: extra outlets in the room (a rarity in old houses but a necessity for travelers), high-speed Wi-Fi, and more than enough hot water for everyone. If you can, book the Turret Room, which has a spectacular ocean view.Continue to 9 of 9 below.
09 of 09
Enjoy all the charm of a secluded cabin in the woods combined with modern amenities (Wi-Fi, cable TV, electric heat) and conveniences of a large resort at the cabins at Point Lookout in Northport. Each of these cabins, which range in size from a one-bedroom queen to a three-bed two-bath that sleeps up to eight people, is built with comfort and relaxation in mind. Unfinished pine walls and rustic furniture give it a truly mountainous feel, and in the larger cabins, a gas fireplace brings the coziness to a whole new level. Each cabin has a fully-stocked kitchenette, as well as a cozy living area.
Though the cabins are tucked away among the pine trees, they are part of a larger resort complex, which gives guests access to the resort’s private beach on Penobscot Bay (a bit chilly in the winter, but if you can bundle up, it’s a beautiful walk), the Copper Pine Cafe, a fitness center, a full bowling alley, an arcade and game room, and a huge network of trails that are perfect for hiking or... snowshoeing. Nearby Belfast and Camden offer shopping and dining if you need a break from rural seclusion (or just a grocery stock-up before you get back to your hideaway).
At TripSavvy, our expert writers are committed to researching and writing thoughtful and editorially independent reviews of the best hotels in your favorite destinations. If you like what we do, you can support us through our chosen links, which earn us a commission. Learn more about our review process.