Family-friendly holiday rentals in Woodland Park

HOT TUB ~ 31 Acres ~Bring ATVs/Border Nat'l Forest

Looking for a quiet and secluded mountain getaway? This charming cabin on 31 acres that borders Pike National Forest is the perfect place to escape the hustle and bustle of everyday life. Enjoy breathtaking views of the surrounding mountains from the cabin's spacious deck, & keep an eye out for wildlife. The mountain getaway vibe is complete with a new hot tub, wood-burning stove & amazing views. You’re just a short drive from several mountain towns and 2 hours from Denver International Airport.

Cabin on Pikes Peak, Hot tub, Walk to Wine + Food

*Brand new nordic spa 6 person hot tub as of April 2026!* 2 bedroom, 2 bath historic cabin backs to wilderness. Enjoy amazing views of the surrounding trees and rocks. Located on Pikes Peak, Hidden Falls cabin is just 10 minutes from Manitou and Colorado Springs but it feels like a world away. Take in the views from your soak in the hot tub or under the outdoor shower. Walk to the Wines of Colorado for libations and food. The cabin is an ideal destination for a restful retreat, a romantic getawa

Little Woody's Hideaway-(4)DownTown - 329662

License 329662. Cozy little 2 story home with 1 bedroom, 1 bath with a pull out sofa sleeper in the center of downtown Woodland Park. It has so much charm you will never want to leave! You have shops and restaurants a hop skip and jump away and the memorial park in your backyard and you can walk to almost EVERYTHING. You will enjoy the farmers market in the spring and summer that is a block away or sit outside and BBQ. Beautiful hikes are 5-20 mins away, we have a guide for all your adventures!

Romantic AFrame*Private Trail*Wood Fire*Stargazing

► Romantic A-frame retreat designed for couples and quiet getaways ► Backyard opens to over one million acres of national forest with a private trail leading to a private summit fire pit ► Outdoor fire pit for stargazing and peaceful evenings ► Thoughtfully designed by a boutique NYC interior design firm ► Well-equipped kitchen for cooking real meals ► Nest mattress with organic cotton sheets for deep sleep ► Easy access to hiking, skiing, gold-water fly fishing, scenic drives, and ATV rentals

Wabi Sabi Tiny House - No Cleaning Fees!

I designed and built this Tiny House a few years ago! As such, it's still an ongoing work in progress and so not quite as picturesque as the finished homes you may see on TV, but it's still fully functional, cozy, and homey. To sleep, you'll have the choice of a queen size loft bed (must climb narrow stairs to access) or a queen size (comfortable!) sofa bed on the ground floor. Located in Woodland Park, CO you have an AMAZING view of Pike's Peak and close proximity to so many adventures 🤗

Views, views, VIEWS I Hot tub I Peaceful 3 acres

🏔️ THIS IS THE REAL DEAL. Come Experience Authentic Colorado Mountain Living 📍 Located just 1 mile from Catamount Recreation Area, a HIDDEN GEM w/ hiking trails & water activities 🌄 CLOSE-RANGE Pikes Peak views right from the property! 🛁 BRAND NEW Arctic Spa hot tub for the ultimate in mountain luxury – soak under the stars! 🛍️ Minutes to downtown Woodland Park for dining, groceries & more ✈️ 1.5 hrs to Denver International Airport (DIA) 🌲 Peaceful forest setting to unplug & reconnect!

Scenic Views, Hot Tub, Firepit, 2 Decks, Dogs YES

Escape to the “Blue Spruce Chalet”. A 900 sq. ft. A-frame (ish!) retreat on 2 private acres in Manitou Experimental Forest, 15 mins north of Woodland Park & steps away from world-class trails & fishing. Explore the outdoors or plan to stay in. Enjoy a fully equipped kitchen, a wood-burning stove, an outdoor firepit, 2 decks with stunning mountain & sunset views and reliably fast WiFi. Star gaze from the hot tub. You may never want to leave this slice of heaven. Perfect for a quick getaway.

Sugar Shack -1930's Cabin-Downtown & Dog Friendly

Stunning remodeled 1930's cabin with one of the best views of Pikes Peak in town! The Sugar Shack has a hot tub with views, dog friendly with a fenced-in backyard, and foosball table for fun times. It offers unique charm and is nestled in the heart of downtown and located one block from beautiful Memorial Park and Main street. Walk to restaurants, a brewery and shopping. Watch TV on a LED smart TV's. Or catch live sporting events on Dish Satellite. Stocked kitchen for home cooked meals.

Sunny Treetop Tiny Home! Beautiful Pikes Peak View

Welcome to Treetop Tiny Home! My home is nestled in an adorable close knit Tiny Home community in the lovely town of Woodland Park, Colorado! Come and escape the hustle of this busy world, and enter into the peaceful tranquility of tiny home living... in the woods. Woodland Park is centrally located to some of the finest attractions Colorado has to offer: Just minutes to Rampart Reservoir, Pikes Peak, The North Pole, Cave of the Winds, and so many beautiful hikes! Insta @treetoptinyhome

Serene Riverside Cabin: Hot Tub, Fire Pit, Patio

With a river in the backyard next to the private hot tub and massive gas fire pit for all of your party, what more could you need?! If you love watching local wildlife cross over a creek on a luxurious back patio that’s perfect for all seasons, then you should book here. Enjoy the full amenities of a kitchen stocked with a curator’s touch, heated towel rack, remote control gas fireplace, gas grill, 2023 top-to-bottom remodel. Book RiverHouse North, by Forest & Peak Retreats, today!

A-frame, Tiny home, Hot tub, 3 acres, Sleeps 4!

Kick back and relax in this stylish tiny home A-frame on 2 acres for a romantic getaway or time with your family. • Hot tub • Sleeps 4 • Indoor fire place & outdoor propane fire pit • Fully stocked coffee bar provided • Board games • Off-road trails & rentals in town all year • 15 minutes to Pikes Peak Entrance • 25 mins to Cave of the Winds • 35 mins to Garden of the Gods • Secluded & outside of city limits, yet minutes to town • 45 minutes to CO Springs Airport

Pine & Pond ☆ Newly Renovated Woodland Park Cabin!

Nestled in the cozy mountains outside of Pikes Peak, this earthen home comes well-equipped with 4 bedrooms, 6 beds and 2 bathrooms for your luxurious getaway. King bed, tons of games, and child friendly amenities await! Brand New Hot Tub just installed with gorgeous views!! The home has fantastic access to Garden of the Gods, downtown Woodland Park and all of the hiking, fishing and exploring that you're looking for. Come for the retreat you deserve!