Family-friendly holiday rentals in Cascade-Chipita Park

Guest suite in Cascade-Chipita Park

A wooden structure features a spacious deck with a rustic railing. A green sign displaying 'Picabo Meadow' and 'Welcome' hangs prominently, inviting guests into the guest suite. Natural wood tones reflect a cozy atmosphere beneath the elevated deck.

4.9 out of 5 average rating, 115 reviews

Picabo Meadow - a 2BR suite w/ a separate entrance

Picabo Meadow is a spacious 2BR guest suite retreat. A hidden gem offering peaceful relaxation and seclusion, yet is only minutes away from hiking trails, restaurants and attractions to visit and enjoy. Picabo Meadow is a great base for your skiing adventure. We’re centrally located to all the main skiing venues: Breckenridge, Keystone, Monarch, Arapahoe Basin, Loveland and Eldora. Most are just a couple of hours away. You’ll find that there is more variety in this area and prices are better.

Cabin in Green Mountain Falls

A living area features a neutral-colored sofa adorned with patterned cushions, complemented by a wooden bench. A decorative coffee table sits in front, with subtle lighting provided by lamps. The kitchen area showcases modern cabinetry, while floral curtains frame large windows, inviting natural light.

4.93 out of 5 average rating, 123 reviews

Blue Sparrow's Nest

Blue Sparrow's Nest cabin is surrounded by whispering mountains, enchanting winds and grand views of the mountain peaks. It's home to gorgeous colorful birds that you will see during your stay. It's a fully renovated 2 - bedroom home with modern Luxe Interiors and 2 smart 85 inch SONY televisions. It comes with huge deck, large outdoor table set for 6. The sights and sounds surrounding this destination are experienced by few. With large deck and sound of nature can be enjoyed night and day.

The cabin is partially obscured by falling snow and surrounding foliage. A wooden deck with railings is visible, extending out from the front of the structure. The scene captures a peaceful winter atmosphere in a snowy mountainous setting.

4.98 out of 5 average rating, 355 reviews

Modern Luxury Cabin~ Hot Tub~Pet Friendly~

You love mountains. We do too. But, you also love luxury. You've got good taste. That's why The Baer's Den is perfect for you. It brings to life that rare blend of modern luxury and mountain mystique only Colorado can provide. Add handcrafted sensibilities to this magazine-ready cabin and you're sure to fall in love. With nearby trails, quick access to local hot spots, and the ever-present Rampart Range viewable from the stylish deck, you can't miss The Baer's Den. Did we mention the hot tub?

Tiny home in Woodland Park

The exterior of a tiny house features a combination of green and wood paneling. Large windows allow ample natural light, while a welcoming door with steps leads inside. Gravel surrounds the house, enhancing the natural setting among surrounding trees.

4.93 out of 5 average rating, 565 reviews

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 🤗

The cabin's exterior is framed by tall trees, showcasing a welcoming front porch with steps leading to the entrance. Natural materials blend with the surrounding landscape, and sunlight casts a gentle glow on the roof. Lush greenery and decorative stones enhance the setting.

4.99 out of 5 average rating, 167 reviews

Classic Throwback Colorado Mountain Cabin

Take it easy at this unique and tranquil getaway. A family cabin crafted in the 1940s, unchanged with the exception of tastefully done upgrades and improvements. Authentic western decor and knotty pine interior. Easy access to nearby hiking and attractions. Minutes from the beautiful small mountain towns of Green Mountain Falls, Manitou Springs and Woodland Park. Local attractions including Pikes Peak, North Pole Santa’s Workshop, Cripple Creek, Garden of the Gods are just minutes away.

An aerial view showcases a relaxing outdoor space featuring a hot tub beside a shallow creek. A small bridge crosses the creek, while a fire pit and seating area are positioned nearby among lush greenery, creating a serene retreat atmosphere.

4.98 out of 5 average rating, 115 reviews

Creekside Cowboy Cabin with 360° Mountain Views

Welcome to the Creekside Cowboy Cabin, an outdoor creek side retreat. Experience an authentic cowboy cabin where you can escape city life. Kick off your boots and relax by the creek, soaking in the beauty of Colorado's Rocky Mountains! Nestled in Pike National Forest, there is access to hiking, biking, ATV trails, and reservoirs, with stunning 360° mountain views. Pet, family, group, and business traveler friendly! 20 minutes to Downtown Colorado Springs and located in the heart of nature!

Treehouse in Cascade-Chipita Park

The unique octagon structure of the Treehouse is surrounded by lush greenery, with tall trees and fog creating a serene atmosphere. The design elevates the home above the forest floor, showcasing wooden supports and inviting outdoor stairs leading up to the entrance.

4.99 out of 5 average rating, 286 reviews

THE Treehouse, Panoramic Views, CoffeeBar, KINGBed

*If booking a stay for Oct.-May please carefully read winter info. Welcome to the Treehouse - the ultimate Colorado getaway. Perched high in the trees with panoramic views, you’ll never want to leave. This completely remodeled, octagon treehouse is just 15 minutes from most attractions in Colorado Springs and 5 minutes from the famous Pikes Peak Highway and gorgeous hiking trails - you are right in the middle of plenty to do while also being tucked away in your own little forest paradise.

Train in Cascade-Chipita Park

The exterior of the converted caboose is showcased amidst tall blue spruce pines, featuring a vibrant red color. The surrounding area offers ample space for outdoor activities on a gravel path, with lush greenery visible in the background.

4.97 out of 5 average rating, 209 reviews

Rustic Railway Retreat - 10 min from Co Springs

Get away from your busy life. Nestled along Fountain creek bubbling beneath pines and mountain views this train caboose is the perfect place to relax, unwind and explore. Enjoy nature overlooking the creek from your private hot tub on the deck. Located within walking distance of secluded hiking trails and the Wines of Colorado. Santa's Workshop and Pikes Peak highway a minute away. Manitou Springs and Old Colorado City are a 7 minute drive. Personalized guidebook https://abnb.me/IVMEUfL3aIb

The cabin's exterior showcases rustic wood siding surrounded by lush trees and large boulders. A spacious deck equipped with string lights enhances the inviting ambiance. A picnic table and a gas grill are situated on the patio, offering a charming outdoor dining experience.

4.99 out of 5 average rating, 221 reviews

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

Gorgeous in every season, this 2 bedroom, 2 bath historic cabin backs to wilderness and has amazing views of the surrounding mountain peaks. Located on the base of Pikes Peak, Hidden Falls Cabin is just 10 minutes from Colorado Springs but it feels like a world away. Take in the views of surrounding forest and rock formations from your morning soak in the hot tub or under the outdoor shower. The cabin is an ideal destination for a restful retreat, a romantic getaway, and adventure hub.

Cottage in Cascade-Chipita Park

A charming cottage is surrounded by vibrant orange poppies and lush greenery. The entrance features a red door and blue accents, while a picnic table is visible nearby, offering an inviting outdoor space. The unpaved driveway leads to the cottage, framed by trees.

4.85 out of 5 average rating, 293 reviews

Cottage w/Mountain Views |Perfect Couples Retreat

Charming and newly updated cottage has every amenity of a modern stay with the location and stunning views of a remote mountain retreat. Nestled at the base of Pikes Peak, this cozy getaway is perfect for couples or friends seeking adventure and relaxation. Located just 10 minutes from both Colorado Springs and Woodland Park, you’ll have easy access to the best the Pikes Peak region has to offer. Wake up to breathtaking mountain views and make memories in this idyllic setting.

Guest house in Colorado Springs

The inviting Inlaw suite features a comfortable queen-sized bed adorned with a soft quilt, complemented by framed artwork on the wall. A cozy couch sits opposite the bed, and a ceiling fan offers a gentle breeze. Light streams through the window, illuminating the space.

4.95 out of 5 average rating, 606 reviews

The Bonnyville Suite

Cozy Inlaw Suite in the Bonnyville Neighborhood nestled within the center of the city with easy access to I-25. Have fun with all the local entertainment that downtown Colorado Springs has to offer. See the top of Pikes Peak, Olympic Training Center, Air Force Academy, Zoo, hike Garden Of The Gods & Seven Falls. Experience the many breweries & wineries in our area. Walking distance from grocery store, coffee shops, a park, trails, and a small shopping center.

A warm living area features large windows framing scenic views of surrounding trees. The space includes a leather sofa, a loveseat, and an accent chair arranged around a coffee table, complemented by a patterned area rug and a lamp that adds soft lighting.

4.93 out of 5 average rating, 120 reviews

The HeartRock House in Cascade

Welcome to the Heart Rock House in the beautiful mountains of Cascade, Colorado! ✓ 8 mins to the famous Pikes Peak Highway and Manitou Springs ✓ Expertly cleaned home ✓ I love 5 minutes away and am super responsive to texts and messages ✓ Ultra-fast, reliable internet ✓ Perfect for a family retreat in the mountains ✓ Game room with foosball and air hockey tables ✓ Deck for enjoying Colorado's sunny weather+mountain views+grilling up meals

Popular amenities for Cascade-Chipita Park family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 116 reviews

An outdoor space features a fire pit surrounded by several adirondack chairs on gravel. A private hot tub is visible in the background alongside a barbecue grill. String lights hang above, illuminating the scene as a pastel sunset colors the sky.

Home in Colorado Springs

Hot Tub + Fire Pit + Grill | Long Stays, Fast WiFi

4.92 out of 5 average rating, 527 reviews

A rustic mountain cabin is nestled among lush green trees, elevated on a rocky terrain. Surrounding vegetation includes tall pines and bushes, with a peaceful hillside backdrop under a clear blue sky, creating a tranquil and inviting environment.

Cabin in Florissant

Fawn Cabin, On 5 Private Acres With Hot Tub!

4.98 out of 5 average rating, 164 reviews

The image collage features four areas of the Tecumseh Lodge. A living room showcases a leather sectional, a stone gas fireplace, and large windows displaying snowy trees outside. The loft bedroom displays a queen bed with a cozy couch, while the downstairs master bedroom features a king-size bed and beautifully arranged bedding.

Chalet in Woodland Park

Cozy Forest Escape w/ Hot Tub & Scenic Views

4.98 out of 5 average rating, 185 reviews

A hot tub bubbles in the foreground, illuminated by soft, warm lighting. The exterior of the home is visible in the background, featuring light gray siding and two doors leading inside. The evening sky showcases scattered clouds and fading light.

Home in Colorado Springs

Backyard Hot Tub Oasis Minutes From Everything!

Guest house in Colorado Springs

An aerial view of two red structures highlights the Mountain Retreat guest house adjacent to the host's residence. Both buildings feature green roofs, surrounded by trees and landscaped outdoor areas. Patios with seating and vibrant flowers enhance the inviting outdoor setting.

4.98 out of 5 average rating, 594 reviews

Mountain Retreat near Pikes Peak and attractions!

Tiny home in Cascade-Chipita Park

A kitchen table is set with a bottle of wine and two elegant glasses, accompanied by neatly folded navy blue napkins placed on woven placemats. Soft natural light enters through a nearby window, illuminating the wooden dining surface and surrounding kitchen features.

4.98 out of 5 average rating, 227 reviews

Tiny House in the Mountains, Hot Tub & EV Charger

Guest suite in Colorado Springs

A hot tub is illuminated with soft blue light, set on a private patio. String lights decorate the area, enhancing the outdoor atmosphere. In the background, a staircase leads to a spacious wooden deck surrounded by trees, creating a serene setting at dusk.

4.97 out of 5 average rating, 264 reviews

The Black Forest Estate

4.92 out of 5 average rating, 203 reviews

The exterior of the mountain home is portrayed, featuring wood siding and a large deck that wraps around the structure. Surrounding pine trees and natural landscape are visible, enhancing the privacy of the property. The sloping mountains in the background complete the serene setting.

Cabin in Woodland Park

Lost Antler Lodge(6)-hottub/3acres/near town/views

Family- and pet-friendly home rentals

Guest house in Palmer Lake

A rustic wooden cabin is nestled among snow-covered trees, presenting a serene winter scene. The building features a sloped roof and a single satellite dish, surrounded by a blanket of snow on the ground. The town of Palmer Lake is visible in the background.

4.94 out of 5 average rating, 254 reviews

Quaint and Historic Studio Cabin

4.97 out of 5 average rating, 688 reviews

A charming exterior view of a cabin-inspired home is surrounded by lush greenery and vibrant flowers. Stone pathways lead to a welcoming entrance, accentuated by light blue walls and a small patio featuring two chairs. Mature trees provide shade and enhance the natural setting.

Guest suite in Broadmoor

Canon Getaway- Cabin inspired home

4.88 out of 5 average rating, 393 reviews

The eco-cabin exhibits a modern exterior with a mix of reclaimed wood planks and a stone foundation. The elevated structure features a welcoming front porch, framed by sturdy railings and illuminated by recessed lighting.

Cabin in Florissant

Rock Rest Eco-Cabin

Guest suite in Colorado Springs

A stone pathway meanders through a grassy yard, bordered by flowering plants. Lush greenery complements the landscape, with two clusters of blooming irises standing out. Residential homes are visible to the right, creating a peaceful neighborhood setting.

4.83 out of 5 average rating, 339 reviews

Private Studio on urban homestead Central #0633

4.88 out of 5 average rating, 410 reviews

The cabin's exterior showcases rustic wooden logs juxtaposed with modern elements. A welcoming red door is surrounded by simple landscaping, including a bench and a small tree. The entrance provides a view of the nearby road and surrounding trees, adding to the cabin's quaint charm.

Cabin in Woodland Park

Cabin with Pikes Peak View in WP License#329434

4.93 out of 5 average rating, 210 reviews

A scenic view reveals rolling hills adorned with evergreen trees. Snow-dusted peaks stretch across the horizon, complemented by a diverse landscape featuring both dense forests and open spaces. The atmosphere reflects tranquility, with soft light casting a gentle glow over the vast wilderness.

Cabin

Red Door Cabin

4.97 out of 5 average rating, 215 reviews

Cabin in Florissant

Whimsical Dreams Cabin | Firepit | Kids Fort

Superhost

A spacious deck features a lighted gazebo shaded by draped fabric. Two lounge chairs with red cushions are positioned nearby, along with a sectional couch arranged around a dark coffee table. The backdrop includes wooden fencing and greenery beyond.

Apartment in Colorado Springs

4.92 out of 5 average rating, 223 reviews

Contempo Downtown COS condo. Deck*Yard*Fire pit

Family-friendly home rentals with a pool

Guest house in Colorado Springs

An indoor pool area features a 35 ft heated swimming pool underneath a spacious glass enclosure. Two swan-shaped pool floats rest on the water, while lounge chairs are positioned along one side, providing a relaxing atmosphere. Natural light streams through the large glass walls.

4.92 out of 5 average rating, 111 reviews

Urban Float - Private Heated Pool/HotTub & Firepit

4.92 out of 5 average rating, 236 reviews

A bright living area is furnished with a green sofa and a white slipcovered couch. A wooden coffee table sits in front. A dining table is positioned near a window, allowing natural light to illuminate the space. Decorative plates and a world map adorn the wall.

Flat in Colorado Springs

Quite Spacious Apt w/ Game Table, Bball Court

4.94 out of 5 average rating, 17 reviews

A well-maintained grassy yard is framed by a white picket fence. A large tree and decorative plants are visible, alongside a small swing set. The exterior of the house features large windows and is accompanied by a storage shed in the background.

Guest suite in Fountain

Settlers Pass apartment to experience Colorado

4.88 out of 5 average rating, 132 reviews

An outdoor patio area is highlighted by a wooden frame, providing shelter over a dining table and seating. A hot tub is situated nearby, surrounded by lush greenery and tall trees, creating a serene environment for relaxation.

Home in Woodland Park

Sunshine Mountain , experience true Colorado!

A rustic log cabin is set against a backdrop of lush greenery, featuring a wrap-around deck adorned with vibrant flower pots. Sturdy wooden stairs lead to the entry, surrounded by natural stone accents and shaded by tall pine trees.

4.97 out of 5 average rating, 161 reviews

Rustic Historic Colorado Mountain Cabin Pikes Peak

Townhouse in Colorado Springs

A sunlit bedroom showcases a spacious bed layered with crisp white linens and dark pillows. Light streams through large windows adorned with floral curtains, creating a warm ambiance. A bedside lamp complements the natural lighting, enhancing the inviting atmosphere of the space.

4.99 out of 5 average rating, 100 reviews

*King Bed*2CarGarage*Gym*Workspace*EVCharger*

Home in Garden of the Gods

An indoor area features a spacious pool illuminated in blue, complemented by bright skylights above. A jacuzzi is positioned to one side, while a seating area with a sectional sofa and plush chairs is visible, offering a relaxed space for guests.

4.97 out of 5 average rating, 30 reviews

Indoor POOL, Hot Tub, Sauna! Garden of the Gods