Holiday rentals with outdoor seating in Winter Park

Incredible water front Cabin w/ HOT TUB & kayak!

Escape to our stunning cabin right on the water, with breathtaking views of Rocky Mountain National Park. Newly upgraded with a spacious deck and hot tub, it's the perfect retreat for unwinding after a day of adventure. Whether you're kayaking the lake, spotting wildlife from your doorstep, or simply soaking in the views from the hot tub, this location offers endless relaxation and exploration. This cabin provides something special for everyone. Book now for an unforgettable Grand Lake getaway!

Cozy Cabin Views : Hot Tub, Golf, RMN Park & Lakes

Discover this special retreat in a prime location of Grand County, surrounded by a mountain playground. Secluded yet only 15 mins to Winter Park, 10 mins to Granby, 20 mins to the lakes, 5 mins to a world class 27 hole golf course and endless hikes all around. Enjoy panoramic south and west-facing views for stunning sunrises and sunsets. Relax on the large deck and hot tub. Inside, experience cozy cabin vibes with our open floor plan, remodeled kitchen, custom wood finishes and two fireplaces

Best WP spot! 1/2 block to shuttle Private hot tub

*Nicest 5 bd Townhome in Downtown WP *Corner unit w/ 180 degree views *Sleeps 12 via 7 beds *Walk blocks to best restaurants and bars *Kid's Park & Skate Park across street *Best XC Mountain Biking is .5 miles away. *1 block to the free shuttle to Ski/Trestle *Private 7-person rooftop Hot Tub to watch concerts *Private Massage Chair *Private Fire Table *Nectar & Purple Mattresses *6 Roku Smart HDTVs *Sonos Surround Sound *1Gbps Comcast Fiber Internet *Bosch Appliances *Home Office *Bunk Room

Rustic Glam Mountain Escape - Near Downtown/Trails

Renovated mountain townhome hosted by experienced, 5-star Superhosts! After exploring nature and enjoying downtown Winter Park, soak your tired legs in the private, indoor hot tub. Kick up your feet, and nestle up in front of the crushed glass fireplace. Enjoy the mountain views and warmth of the afternoon sun in the solar room. Cook a gourmet meal in the brand new granite/stainless steel/marble kitchen. Do it all over again after laying your head down to rest on luxuriously-appointed beds!

Ideal Winter Park Retreat – Ski, and Relax!

This fantastic end-unit townhouse offers the perfect blend of convenience and serenity. Located on the shuttle line and just minutes from town, it’s nestled among towering pines for a peaceful, secluded feel, yet close to all the action. Featuring stunning mountain views, this light and bright home includes: private hot tub with views, fully-stocked kitchen, and split level bedrooms for privacy. The perfect base for all your Winter Park adventures—whether skiing or just unwinding in nature!

Location, decor, amenities you’ll love + hot tub!

Conveniently located within short walking distance to Winter Park's Main St., two bus stops (with free transport to resort) , Rendezvous hiking and mountain biking trails, groomed cross-country ski trails, Fraser bike trail and recreation center. 'Peppers+Pines' is a one-of-a-kind modern mountain home with exceptional amenities including 3 bed, 3.5 bath, 2000 SF, large 2-car garage, EV, private hot tub, Wi-Fi, Apple TVs, Sonos, Breville espresso, and beautiful decor. See IG peppersandpines.

Luxe Vacay Spot - Golf, Hiking, Biking & More

Perfect home base for outdoor adventures and family vacations. This gorgeous home overlooks the golf course with stunning mountain views all around and a short walk to the Grand Elk Bar & Grill. Inside, you'll find two inviting living areas, chef's kitchen, two eating spaces, cozy seating around the fireplace, and smart TVs. 4 bdr, 3.5 ba, and workspace. Close to Winter Park, Granby Ranch, Grand Lake and RMNP. Free bus from City Market to Winter Park drops you by the gondola.

Overlook Lodge (Hot Tub + Private Creek)

Welcome to the Overlook Lodge! Retreat to our cozy log cabin tucked away in the St. Mary's Glacier community. Gaze (or hike) out into the surrounding mountains, relax by the private creek next to the lodge, or go fishing at the 2 nearby lakes. Great for small groups, families, and couples looking to spend time in nature - whether you're seeking adventure or tranquility, you'll find it here! Near Denver, Skiing, Red Rocks, and steps away from St. Mary's Glacier hiking trail.

New Rooftop Loft 33 I Free Adventures Daily

Have the ultimate Rocky Mountain experience when you stay at this brand new, custom loft in the heart of downtown Winter Park including a spacious rooftop with a private hot tub. This luxurious 3 Bedroom / 3 Bathroom home sleeps up to 10 people, with enough room to spread out comfortably in this impressive 2000 square feet of luxuriously appointed living space, which includes 1 Queen Bed, 1 Full over Twin Bunk,1 Sleeper Sofa/Day Bed and a Pack and Play Portable Crib.