Winter Family Vacations for All Kinds of Travelers

Whether it’s racing down the ski slopes or cozying up by a fireplace, winter is packed with great vacation opportunities. So, if you’re looking to have a little family fun on your next winter getaway, you’ve come to the right place. We’ve put together a list of the best spots in America for winter family vacations.

Winter Family Vacations for Skiers

As temperatures drop, some of the most popular things to do are winter sports. Whether it’s snowboarding, ice skating, or (especially) skiing, these activities are some of the best ways to take advantage of the season. Of all the spots for skiing, one of the best for the whole family is Jackson, Wyoming. Jackson is home to not one, but two of the best ski destinations in the country, making it one of the best spots for winter family vacations. If you want slopes with some serious altitude, you want Jackson Hole Mountain Resort. Jackson Hole Mountain boasts a vertical drop of over 4,000 feet, the largest in North America, and primarily features expert and intermediate slopes. That means that while these slopes aren’t for the faint of heart, they’re great for families with teens who love a challenge.

Meanwhile, Snow King is a great option for less experienced skiers, with a spectacular beginner zone. Of course, those who want a challenge will still find plenty to enjoy across its 41 named runs. On top of these two great ski spots, you’ll be able to enjoy over 200 miles of cross country skiing in trails found in Grand Teton National Park, the Bridger-Teton National Forest, and more. Not to mention, you’ll still be able to enjoy ice skating and snow tubing in the area. There’s no shortage of fun things to do in Jackson, Wyoming!

Where to Stay in Jackson, Wyoming

Naturally, if you’re planning a winter family vacation, you’ll want a good place to stay. Fortunately, there’s a great place to stay that’s just a short drive away from the best slopes in the state: Anvil Hotel & Cache House. You’ll have a great view of the mountains from this boutique hotel, and the view alone makes it a great place to stay for your next winter vacation. Of course, there’s also some luxurious amenities and stellar accommodations to make your stay extra cozy.

Amenities

Accommodations

• Standard Queen: features a queen bed and bathroom. Accommodates two guests.
• Standard King: features a king bed and bathroom. Accommodates two guests.
• Standard Two Queen: features two queen beds, a bathroom, and a small seating area. Accommodates four guests.
• Family Bunk Suite: features a queen bed, bunk bed, and two bathrooms. Accommodates four guests.

Winter Family Vacations for Taking It Easy

While racing down the ski slopes is a lot of fun, not everyone wants those kinds of thrills on their winter family vacation. Fortunately, there’s another destination with plenty to do if you just want to soak up the winter atmosphere: the Catskills. This region in New York turns into a winter wonderland as the year comes to a close. This means that the area is packed with fun winter vacation ideas. Snowshoeing is a fun way to explore the snow and isn’t quite as intense as skiing. You can also go sledding for another family-friendly activity. Not to mention, there are plenty of sleigh rides you can enjoy all around the area, some of which even come with hot chocolate!

If you want to see the beauty of nature in the middle of the winter, be sure to stop by the Mountain Top Arboretum. This public garden in the Catskills is dedicated to showcasing the beautiful native plant communities of the northeast. You’ll see 178 acres of plant collections, natural meadows, wetlands, and more! Additionally, if there’s one thing the Catskills have a lot of, it’s water. But what happens when all that water begins to freeze? Well, ice fishing goes into full swing of course! For most parts of the country, ice fishing is only possible around this time of year. So you’ll want to take advantage of it while you can. Overall, the Catskills are filled with kid-friendly activities that make it a great place for winter family vacations that are a little more laid back.

Where to Stay in the Catskills

Looking for a cozy hideaway in the Catskills for your winter family vacation? Well, look no further than Callicoon Hills! You’ll find this property nestled in the woods surrounding the Catskills, which gives it a sense of peaceful isolation. The sense of peace and quiet you’ll get from Callicoon Hills is great on its own, but there’s even more to love than that.

Amenities

Accommodations

• Pool House King Room: A conventional room with easy access to the pool and patio. Features a king bed and bathroom. Accommodates two guests.
• Tree House King Room: Another more conventional room for a classic vacation feel. Features a king bed and bathroom. Accommodates two guests.
• Deck House Standard King Room: A secluded room located on the ridge that overlooks the rest of the property. These rooms are dog-friendly. Features a king bed and bathroom. Accommodates two guests.
• A-Frame Cabin: A striking, distinct cabin with a floor-to-crown window. Features a queen bed. Accommodates two guests.
• Creekside Cabin: With 300 square feet of space, the Creekside Cabin is perfect for larger travel groups. Here, you’ll have great views of the creek and plenty of contemporary amenities. Features two king beds, a sofa bed, two bathrooms, and a full kitchen. Accommodates six guests.

Winter Family Vacations for Escaping the Cold

Want a winter family vacation without the winter weather? We can’t blame you! The snow and ice around the holiday season isn’t for everyone. So, if you’re trying to get away from that kind of weather, a trip to the Big Island of Hawaii should definitely be in your future! This island is packed with opportunities for aquatic adventures. You can swim with manta rays, go whale watching, or enjoy surfing at one of the island’s many beaches. Speaking of beaches, there are plenty of types to enjoy here. In fact, you can unwind at white, black, and even green-sand beaches that encircle the island’s 266 miles of coastline. Of course, it should come as no surprise that these beaches are a prime spot for snorkeling and scuba diving too. There’s no shortage of Big Island golf courses if you want to practice your swing, as well.

Even the Grand Canyon National Park runs the risk of snow in the winter season, but the Hawai’i Volcanoes National Park stays warm all year round. So, if you’re looking to escape the cold, what better way is there to do it than by seeing two of the world’s most active volcanoes? You’ll also have the chance to witness the dynamic processes of volcanic activity and walk across ancient lava flows. It’s also a UNESCO World Heritage Site! Want a truly transformative experience? Then step into the Kona Cloud Forest Sanctuary. Founded in 1982, this sanctuary is a carefully preserved cloud forest where you can experience true serenity during its peaceful tours and yoga sessions. When you want a bit of warm weather in the winter, you can’t go wrong with Hawaii!

Where to Stay in Hawaii

When it comes to boutique hotels in Hawaii, it doesn’t get better than Pacific 19. Renovated in 2023, Pacific 19 exudes a modern, sleek style. It’s conveniently located near plenty of kid-friendly attractions so you and your family will have no trouble reaching the fun on your winter vacation. Of course, this boutique hotel is no slouch when it comes to amenities and accommodations either. So, you’ll be well taken care of when you stay here.

Amenities

Accommodations

• Guestrooms: feature either a king bed or two double beds, bathroom, private balcony, and macrobar. Accommodates two to four guests.
• Ohana Suite: features a king bed, sleeper sofa, two bathrooms, and a living room. Accommodates four guests.
• Apartment Suite: features a king bed, sleeper sofa, kitchenette, bathroom, and a living room. Accommodates four guests.

Want More Inspiration for Winter Family Vacations?

If you love to broaden your horizons and explore new places, welcome—you’re in good company. At Nook Outdoors, we’re always on the lookout for new adventures. That’s why we’ve cultivated a list of vacation properties that are just off the beaten path. So, whether you want to go horseback riding in the countryside or experience glamping in the woods, we’ve got you covered. Click on the link below to see more exciting vacation ideas. Not just for winter family vacations, but all kinds of getaways.