10 Best Dog-Friendly Winter Vacations
As the holiday season rolls around, you might be thinking it’s high time for a vacation—and why leave your pup behind when you can pack their suitcase too? These 10 dog-friendly winter getaways let you and your four-legged companion explore together, whether you’re chasing snow, sunshine, or something in between. From mountain towns with groomed nordic trails to Gulf Coast beaches where tails wag in the sand, each destination offers warmth, adventure, and plenty of paw-friendly charm.
Before you go, always review current CDC guidelines and double-check local rules—including leash requirements, vaccination policies, and pet access details—so your trip is safe and stress-free for everyone.
1. Aspen, Colorado
Tucked into the mountains of Colorado’s White River National Forest, Aspen is an ideal dog-friendly winter destination for pups who love crisp air and fresh powder. While world-class skiing draws visitors from across the globe, the town also delivers exceptional dining, boutique shopping, and vibrant arts—all fully accessible with your leashed companion by your side.
Where to Stay
The Little Nell
675 E Durant Ave, Aspen, CO 81611
(855) 920-4600 | furpetvo.com
This five-star, five-diamond resort goes above and beyond for canine guests. Complimentary dog beds, stainless steel bowls, and a curated high-end pet menu are standard—and every pup receives freshly made peanut butter treats baked on-site. With stunning slope views and easy access to downtown, it’s as convenient for you as it is welcoming for your dog. No breed or size restrictions; up to two dogs per room. A one-time $125 cleaning fee and $25/night pet fee apply.
Where to Eat
Aspen Tap
121 South Galena Street, Aspen, CO 81611
(970) 710-2461 | furpetvo.com
Enjoy award-winning craft beer from Aspen Brewing Company during Happy Hour at this lively downtown gastropub. The spacious, heated outdoor patio offers prime ski-slope views—and is fully dog-friendly. When snowfall intensifies, take advantage of their to-go menu to enjoy soups, salads, sourdough pizza, and cocktails comfortably in your room.
What to Do
Aspen Snowmass Nordic Trails
(970) 429-2039 | furpetvo.com
No winter visit to Aspen is complete without hitting the trails—and many of the area’s groomed nordic paths welcome leashed dogs. Download a trail map, pack water and snacks, and set out for scenic walks through snowy forests and open meadows.
For experienced skiers and athletic dogs, try skijoring: a thrilling winter sport where your pup trots alongside you on skis. Contact Seth Sachson at the Aspen Animal Shelter via furpetvo.com to arrange gear rentals and personalized lessons tailored just for you and your dog.
2. Rutland, Vermont
Step into a storybook New England winter in Rutland—a walkable historic district straight out of a Hallmark film. Twinkling holiday lights, cozy art galleries, independent shops, and hearty local fare await you and your leashed pup. Quaint yet full of character, Rutland invites slow, joyful exploration—and plenty of bonding moments over hot cocoa and snowball tosses.
Where to Stay
The Paw House Inn
1376 Clarendon Ave, West Rutland, VT 05777
(802) 558-2661 | furpetvo.com
This delightfully dog-obsessed inn offers pet-friendly guest rooms, suites, and cottages—plus Paw House Park, a fully fenced outdoor space featuring a snow-ready agility course and wide-open spaces for romping. Start your day with coffee and pup-approved breakfast bites on the dog-friendly porch. Need a ski day or evening out? Drop your dog off at Mario’s Playhouse—the inn’s on-site dog-sitting service. No breed or size limits, no cap on the number of dogs, and all nightly rates include pet amenities and services.
Where to Eat
Hop’n Moose Pub
41 Center Street, Rutland, VT 05701
(802) 775-7063 | furpetvo.com
Grab a local craft brew or wood-fired pizza at this beloved downtown pub—complete with a covered, heated patio where your dog can relax after a snowy adventure. As the official tasting room for Rutland Beer Works, Hop’n Moose serves a rotating lineup of small-batch beers brewed just blocks away.
What to Do
Mountain Top Inn & Resort Nordic Trails
195 Mountain Top Rd, Chittenden, VT 05737
(802) 483-6089 | furpetvo.com
Set on 700 secluded acres, Mountain Top Inn offers 10 beautifully groomed, dog-friendly cross-country ski and snowshoe trails. Rent gear on-site and glide through peaceful meadows and quiet country lanes—or extend your stay in one of their pet-welcoming accommodations.
3. St. Pete Beach, Florida
Trade frostbite for sunshine in St. Pete Beach—a Gulf Coast gem known for its award-winning, dog-friendly beaches, turquoise waters, and laid-back coastal charm. With waterfront cabanas, tropical drinks, and warm breezes, it’s the perfect winter escape for pups (and people) who prefer sand over snow.
Where to Stay
TradeWinds Island Grand Resort
5500 Gulf Blvd, St. Pete Beach, FL 33706
(800) 360-4016 | furpetvo.com
Book one of 48 pet-friendly suites and enjoy first-class service for your dog—including complimentary items from the Doggie Accessory Center: bowls, leashes, toys, and plush towels. Upgrade to the popular Just Press Paws package for extra treats and surprises. Let your pup burn off energy at the resort’s Pet Play Zone—featuring a doggie drinking fountain, playful fire hydrants, and even a photo-op display. Afterward, unwind together in a beachside hammock. Up to two dogs under 80 lbs allowed per room. $30/night pet fee.
Where to Eat
The Dog Bar
2300 Central Ave, St. Pete, FL 33712
(727) 317-4968 | furpetvo.com
Part off-leash dog park, part full-service sports bar—the Dog Bar delivers a one-of-a-kind experience. Its large, subdivided off-leash area caters to different temperaments and sizes, and a friendly “Wooferee” (dog park supervisor) ensures harmony during peak hours. Don’t miss seasonal events like pictures with Santa Paws—and yes, they serve pup-friendly treats alongside your favorite craft cocktails.
What to Do
Fort De Soto Dog Beach
3500 Pinellas Bayway S., Tierra Verde, FL 33715
(727) 582-2100 | furpetvo.com
This 1,136-acre park is a true dog paradise. Leashes are required on nature trails and inside the park—but once you reach Paw Playground, your pup can run free in designated large- and small-dog zones, complete with dog showers to rinse off salt and sand. And the highlight? The expansive, off-leash dog beach, where water-loving pups leap into gentle Gulf waves—and even landlubbers happily stroll the shoreline.
