A Cozy Winter Escape: Cliff House Maine + My Go-To Travel Loungewear

Like many of us, I’ve been craving little getaways to break up the monotony of winter. Instead of hopping on a plane, I’ve been looking for destinations close to Boston that offer a change of scenery without the hassle of long travel days. After years of hearing rave reviews, we finally made it to Cliff House Maine—and I’m excited to share the experience in case you’re planning a winter escape of your own.

Alongside the trip, I also want to highlight the travel staples I relied on—particularly my newfound obsession: Varley’s Doublesoft pieces, which are officially my 2024 wardrobe MVPs.

Travel Outfit of Choice: Luxe Comfort in Varley Doublesoft

For the road trip and our cozy stay, I lived in Varley’s Doublesoft collection. If you’ve ever slipped into their joggers or sweatshirts, you’ll know what I mean when I say it’s hard to go back to regular sweats.

• Fabric: The material is buttery soft yet structured, medium-weight, and keeps its shape all day without sagging. It feels like a little luxury for working from home or lounging in style.
• Fit: At 5’ tall, their 25-inch inseam joggers are a perfect petite-friendly length with a chic cuff at the ankle. They also come in a longer 27.5-inch version if you’re taller.
• Tip: The lighter colors show a faint pocket outline, but darker shades solve that issue.

I paired the joggers with sneakers, a suede tote, and a long coat—it felt elevated enough to step out for dinner without looking like I’d just rolled out of bed.

📍 Available at Nordstrom and Varley directly.

Packing for a Winter Escape

Besides the loungewear, I leaned on my trusty Blondo waterproof boots (a lifesaver in slush and snow), Adidas sneakers for casual outings, and a cozy oversized coat. I’ve learned that practical yet versatile footwear is key when traveling with kids—you want something stylish enough for dinner but durable for playground stops or snowy sidewalks.

Cliff House Maine: First Impressions

Perched dramatically on the cliffs of Cape Neddick, Cliff House is only about an hour’s drive from Boston but feels worlds away. While it’s known as a summer hotspot (think Chatham Bars Inn energy), we found it equally charming for a quiet winter retreat. With a dusting of snow, the property feels like a postcard-perfect New England escape.

This wasn’t a trip filled with sightseeing or packed itineraries—the nearby towns were sleepy, with many businesses closed until summer. Instead, it was about slowing down, enjoying family time, and soaking up the cozy atmosphere.

Rooms & Booking Tips

Our room was spacious, comfortable, and tastefully decorated with coastal-inspired touches. Families will appreciate that some suites include bunk beds for kids—a fun detail that makes the stay extra special for little ones.

Pro tip: We booked through a Virtuoso/Fora travel advisor (shoutout to Sharon @tsuiadventures), which secured us perks like complimentary breakfast, a hotel credit, and even an upgrade to a suite since it was low season. If you’re planning a stay, this route can add value at no extra cost.

On-Site Activities & Family Fun

Cliff House really shines in its amenities, especially if you’re visiting off-season and sticking close to the property:

• Pools: There are three—an indoor pool, a kids’ splash pool (summer only), and an outdoor infinity pool overlooking the ocean. In January, the outdoor pool was far too icy to enjoy (I accidentally slipped in—definitely don’t recommend!). The outdoor hot tub, though, was absolute bliss.
• Spa: Gorgeous views, but fully booked during our stay. Plan ahead if you want treatments.
• Theatre: Family-friendly movies are screened daily, which was a hit with the kids.
• Crafts & Activities: From DIY sailboat kits to Build-A-Bear-style stuffies, these little extras kept the kids entertained.
• Games Library: A rotating selection of board games—perfect for family evenings by the fire.
• “Maine Station”: Complimentary water, coffee, tea, cocoa, and apples on every floor. My kids made it their morning-and-evening ritual.
• Fire Pits & Walking Trails: Ideal for marshmallow roasting or a brisk sunrise stroll along the cliffs.

Dining at Cliff House

We had breakfast each morning at The Tiller, the main restaurant, where the panoramic views of the ocean rivaled the food. Thanks to our advisor perks, breakfast was included—always a welcome bonus with kids in tow.

For casual dinners, Nubb’s Lobster Shack was our go-to. The kids’ menu is well-priced, and the relaxed atmosphere was perfect after a full day of swimming and exploring.

A Quick Stop in York, Maine

On our way home, we detoured to York, just a short drive away, where we visited Nubble Lighthouse, a local playground, and grabbed a bite at York 54. The flatbread sandwiches (the curry chicken was my favorite) and house-made gelato were a standout. It’s a spot we’ll definitely revisit in warmer months.

Final Thoughts

Cliff House Maine might be buzzing in the summer, but a winter stay offers a slower, more intimate experience. For families, the combination of spacious rooms, kid-friendly amenities, and relaxing adult options (hello, hot tub with ocean views) makes it a solid choice.

Pair that with a cozy lounge set like Varley’s Doublesoft joggers, waterproof boots, and a good coat, and you’ve got the perfect recipe for a winter reset—just an hour outside Boston.

Sometimes, the best escapes aren’t about faraway destinations but about carving out time to recharge, right in your own backyard.