Cozy Winter Getaways in New Hampshire & Massachusetts: Where to Stay This Winter
Winter is one of the coziest times to visit New England, whether your idea of a getaway involves fresh snow on the mountain or a quiet weekend wandering a historic downtown. In New Hampshire's White Mountains, skiers and riders have their pick of several mountains within a short drive of one another, while coastal towns like Portsmouth, New Hampshire, and Newburyport, Massachusetts, settle into a slower pace, with walkable streets, waterfront views, and plenty of restaurants to warm up in.
At Seacoast 2 Summit, our vacation rentals stretch from the Massachusetts and New Hampshire coast to the heart of the White Mountains, and we also offer monthly vacation rentals for anyone who wants to settle in for 30 days or longer. This guide covers where to stay for a ski trip, where to book a winter weekend by the water, and a few options for an extended stay this season.
Where to Stay for a New Hampshire Ski Trip
The Mount Washington Valley is one of the easiest places in New England to plan a ski trip, largely because so many mountains sit close together. Attitash Mountain Resort is in Bartlett, Cranmore Mountain Resort rises above North Conway, Wildcat Mountain is just to the north in Pinkham Notch, and King Pine is south of Conway in Madison. A group can ski somewhere new each day and return to the same home away from home every evening .
Our North Conway vacation rentals range from a two-bedroom cabin to a lodge that sleeps a dozen. Below, we list our current selection from smallest to largest.
Camp Conway, Conway
Camp Conway is the coziest home of the group, a two-bedroom, one-bathroom cabin that sleeps four. It suits couples or a small family who want a simple, comfortable base in Conway, with a hot tub on the deck and a fully equipped kitchen with brand-new cabinets as of 2025. The Kancamagus Highway is just minutes away. See dates for Camp Conway and book your stay.
Finley Lodge, Bartlett
Finley Lodge is the closest of the five to the lifts, with Attitash a five-minute drive away and North Conway about 15 minutes down the road. The four-bedroom, two-bathroom chalet sleeps eight and centers on a living room with a gas fireplace and a Smart TV. A downstairs game room with board games gives the group a second place to gather, and the home is dog-friendly with parking for up to three cars. Check availability at Finley Lodge and book before availability runs out.
Strasse Ski Chalet, Bartlett
Strasse Ski Chalet was set up with skiers in mind, right down to the ski rack beside the front door. The three-bedroom, three-bathroom home sleeps eight and sits eight minutes from Attitash and about 20 minutes from Wildcat. Its second-floor great room pairs a gas fireplace and a 65-inch Smart TV with mountain views, while a six-person hot tub stays open all year. The home is dog-friendly and has parking for up to five cars. View Strasse Ski Chalet and reserve your dates today.
Mitten Pines Cabin, Conway
Mitten Pines Cabin gives larger groups room to spread out, with four bedrooms and two and a half bathrooms across three levels and space for 10 guests. It sits on a quiet, wooded street five minutes from downtown Conway and 15 minutes from North Conway, with Cranmore just minutes away. The hot tub runs year-round, a bonus room with shuffleboard keeps everyone busy on cold nights, and the garage has plenty of storage for skis. Check dates for Mitten Pines Cabin and book your stay.
The Ash Lodge, Conway
The Ash Lodge is the largest of the five, with five bedrooms, three bathrooms, and room for 12 guests. It works well for two or three families traveling together or a big group of friends here for a ski weekend. The living room has a large sectional and a gas fireplace, and a foosball and pool table combo adds some friendly competition once everyone is back from the mountain. Book The Ash Lodge for your ski trip today.
Our Recommendations For Your Ski Getaway
Plan on driving.
Most of our mountain homes are a 5 to 20 minute drive from North Conway Village, so a car is the easiest way to reach the slopes, restaurants, and shops.
Bring the right vehicle.
We strongly recommend an AWD or 4WD with winter tires, since roads and driveways in the White Mountains can be steep and covered in snow or ice.
Check the minimum stay.
Some homes require a two-night minimum while others have none. Check each listing for specific requirements.
Where to Stay for a Winter Getaway Off the Slopes
A winter trip doesn't have to revolve around a lift ticket. For travelers who would rather not ski, two of New England's most popular coastal towns for a winter getaway make an easy, comfortable escape, and both are easily enjoyed on foot.
Portsmouth, New Hampshire
Portsmouth fits a remarkable amount into a few walkable square miles along the Piscataqua River. Once one of the busiest seaports in colonial America, the city has held on to its historic character, and the brick storefronts around Market Square are now home to local shops and a dining scene known well beyond the Seacoast. It's the kind of place where a winter day can be as simple as browsing downtown, stopping for a long lunch, and heading back to a warm home in the evening.
Our Portsmouth homes sleep up to six guests, and many are located close to downtown, so restaurants, shops, and the waterfront are never far away. Some include off-street or driveway parking, a few welcome pets, and many offer strong Wi-Fi and a quiet workspace for anyone mixing a getaway with a few days of remote work. Browse our Portsmouth, NH vacation rentals to find the right fit for your dates.
Newburyport, Massachusetts
Just over the state line on the Massachusetts North Shore, downtown Newburyport offers a similar mix of history and waterfront scenery in an equally walkable setting. Its historic brick buildings are home to restaurants, cafés, boutique shops, and art galleries, and the boardwalk along the Merrimack River is a favorite spot for a stroll with a view of the harbor. Plum Island is only about a 20-minute drive away for anyone who wants to see the coastline in its quiet season.
Our downtown Newburyport homes sleep between four and eight guests, with several located just steps from the waterfront and State Street. Booking directly with Seacoast 2 Summit also means fewer fees than you would pay on Airbnb or VRBO. Take a look at our Downtown Newburyport vacation rentals and start planning your winter weekend with us.
Where to Stay for a Month or Longer This Winter
In addition to short-term stays, Seacoast 2 Summit offers Mid-Term Rentals for guests who want to settle in for 30 days or longer. These furnished monthly rentals, sometimes called "winter rentals," are available from November through April across the New Hampshire Seacoast and the Massachusetts North Shore. Here are just three of our homes that are open for extended stays this season that you might want to check out.
Oceanview Oasis, Hampton Beach
This four-bedroom, two-and-a-half-bathroom home sleeps eight in the island section of Hampton Beach, a five-minute walk from the sand. The top-floor kitchen and family room look out over the ocean and harbor, with a private balcony to match. In-unit laundry, a 65-inch Smart TV, parking for four vehicles, and a pet-friendly policy make it an easy place to spend the season. See Oceanview Oasis in Hampton Beach
Circa 1789, Downtown Newburyport
Circa 1789 is a restored historic home in Newburyport's South End, steps from the waterfront, State Street dining, and the Rail Trail. It has two bedrooms with a king and a queen bed, a bathroom with a soaking tub and walk-in shower, and a dedicated work desk with high-speed Wi-Fi. Central heat, in-unit laundry, and two off-street parking spaces round out the stay. Take a look at Circa 1789 in Newburyport
The Garden, Downtown Newburyport
The Garden sits in the middle of downtown Newburyport, a short walk from the waterfront, shops, and restaurants, with Plum Island about 10 minutes away. The home has two queen bedrooms, a living room with a Smart TV, and a dining room that doubles as a workspace. A private fenced yard, in-unit laundry, high-speed Wi-Fi, and off-street parking come with it. View The Garden in downtown Newburyport
Find Your Winter Rental at Seacoast 2 Summit
Every Mid-Term Rental comes fully furnished with utilities included, designated parking, and a 24/7 support line, and many homes are pet-friendly. To see more properties you can book from November through April, visit our Mid-Term Rentals page and fill out the form at the bottom. Our team will get back to you as soon as possible with options that fit your dates and needs.
