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.

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, 354 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.

The inviting main gathering space features warm wood paneling and a stone fireplace, complemented by leather seating. On display are decorative items arranged on shelves above, while a mirror reflects natural light from the kitchen area, creating a cozy and curated atmosphere.

4.98 out of 5 average rating, 260 reviews

Cabin on Pikes Peak w Hot Tub, Fireplace, 500mbps!

This southwestern boho cabin is tucked amongst the trees in a historic, quiet neighborhood at the foot of famed Pikes Peak. With an ample front deck, floor to ceiling windows, and a private, fenced back yard with hot tub, gas fire pit and s'more fixings waiting for you on arrival, the cabin has wonderful forest and mountain view while within 10 minutes of culture and conveniences in Manitou and Colorado Springs. The place to get away for a romantic retreat, family fun, or a working vacation!

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, 284 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.

A hot tub is positioned on a patio beside a gently flowing creek, surrounded by lush greenery. Sunlight reflects off the water's surface, while trees provide a natural backdrop. A portion of the cabin’s exterior and a small storage unit are visible nearby.

4.99 out of 5 average rating, 192 reviews

Creekside Pack Cabin with 360° Mountain Views

Welcome to the Creekside Pack Cabin with 360° Mountain Range Views! Kick off your boots and relax with a drink by the creek, as you enjoy Colorado's beautiful Rocky Mountains! The cabin is in the center of the Pike National Forest and close to hiking, biking, ATV trails, reservoirs, and 360° mountain views! This cabin is pet, family, group, and business traveler friendly! You are: Only 20 minutes to Downtown Colorado Springs In the heart of nature with hiking, fishing, and much more!

A spacious living area features a large leather sectional sofa adorned with decorative cushions. A round coffee table is centered on a patterned rug, while expansive windows frame mountain views, allowing natural light to illuminate the wood-paneled walls and ceiling.

4.99 out of 5 average rating, 113 reviews

Pikes Peak Cabin: Amazing Views, Hot Tub, King Bed

Prepare to be wowed by views! Large windows wrap the dining and living room overlooking the mountain pass. The cabin features luxury furnishings, new kitchen and bathrooms, large outdoor space, fire pit, hot tub, Tesla charger. And it is dog-friendly. Just 15 minutes from Colo. Springs between Manitou and Woodland Park, Vista View Cabin is easily accessible off Highway 24, and close to excellent restaurants, a winery, and outdoor activities, including the bucket list Manitou Incline hike.

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, 291 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.

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

4.97 out of 5 average rating, 287 reviews

Closer to the sun

This cabin is perfect for a couple or single mountain get away. The neighborhood is less than 10 minutes away from Manitou Springs and Woodland Park. The cabin has its own parking, private patio, and everything you need inside. There is a comfy queen size bed with a memory foam pillow top mattress, a fully equipped kitchen for cooking your favorite meals, as well as a spacious bathroom with stand in shower.

Superhost

A private deck features a hot tub and a hanging chair, surrounded by lush trees and mountain views. Sunlight filters through the tree branches, creating a relaxing outdoor space. The deck allows for leisure and enjoyment of the natural surroundings.

Guest house in Cascade-Chipita Park

4.91 out of 5 average rating, 139 reviews

The Love Nest

Welcome to the Love Nest; a couple’s retreat at the foot of Pikes Peak! This cute & cozy cottage is the perfect place to relax & reset. Enjoy a glass of wine on the private deck or soak in the Jacuzzi. Slip into a fuzzy robe & slippers (or something more comfortable) & lounge by the fireplace. Minutes from hiking trials by foot, minutes from Manitou & Colorado Springs by car.

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

4.97 out of 5 average rating, 115 reviews

A modern kitchen space features a sleek white countertop with seating for six, beside a warm fireplace integrated into a black feature wall. A cozy brown armchair is positioned nearby, and ample natural light filters through the window, creating an inviting ambiance.

Cabin in Divide

Romantic Lakefront Cabin - Hot Tub-VIEWS!

4.92 out of 5 average rating, 526 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!

5 out of 5 average rating, 253 reviews

A two-story, contemporary mountain retreat is surrounded by tall trees. The exterior features a black facade, large windows illuminated warmly, and a spacious deck with steps leading to the landscape. The sky presents a subtle gradient of pink and blue hues at dusk.

Home in Woodland Park

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

4.98 out of 5 average rating, 163 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, 287 reviews

A bright seating area features large windows that offer mountain views. Two modern chairs, one in yellow and another in red, are positioned beside a small white table. A decorative plant sits on the table, with pendant lighting hanging from the wooden ceiling.

Home in Manitou Springs

Tree Retreat & Soaking Tub by Garden of the Gods

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!

Cabin in Green Mountain Falls

The rustic cabin is set among tall pine trees, featuring a spacious deck that extends outwards. Wooden stairs lead to the entrance, while stone pathways lined with lanterns create a welcoming approach. Snow lightly covers the ground, enhancing the serene mountain setting.

4.97 out of 5 average rating, 127 reviews

Pike's Peak Chalet

4.98 out of 5 average rating, 725 reviews

A kitchenette features natural wood cabinetry and granite countertops. Built-in appliances, including a coffee maker and microwave, are neatly arranged. A door leads outside, and a small table is placed nearby on a light-colored rug.

Flat in Divide

The Hideaway

Family- and pet-friendly home rentals

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

Superhost

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

4.88 out of 5 average rating, 393 reviews

Rock Rest Eco-Cabin

Guest house in Colorado Springs

A modern living area features a large window that allows natural light to brighten the space. A comfortable leather sofa is complemented by a stylish coffee table and a cozy armchair. A television is positioned nearby, against a backdrop of light-colored walls and decorative artwork.

4.99 out of 5 average rating, 220 reviews

New Luxury 1 - Bed Near Downtown

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

Earthen home in Colorado Springs

The exterior of a unique earthship home is framed by lush greenery and tall pine trees. Large glass windows reflect the surrounding landscape, allowing natural light to illuminate the earth-toned structure. A black door is visible at the front, alongside a small seating area.

4.99 out of 5 average rating, 189 reviews

Off-grid, Earthen home in the forest!

Guest suite in Colorado Springs

A spacious living area features comfortable seating arrangements including a sectional sofa and armchairs, with a wooden coffee table at the center. A 50" smart TV is positioned for viewing, and a wood fireplace is located to the right. Stairs lead to the upper level.

4.89 out of 5 average rating, 208 reviews

Convenient Old Colorado City Apartment

4.96 out of 5 average rating, 104 reviews

The cabin is set among lush trees, featuring a welcoming porch with seating. A wooden staircase leads up to the entrance, accentuated by natural earth tones. An American flag is displayed, adding to the charm of this mountain retreat.

Cabin in Divide

Skyfall Valley Cabin

Guest suite in Colorado Springs

A studio apartment is shown, featuring a spacious bed with a neutral-toned blanket. A small dining area with two chairs and a table is visible. A kitchenette is equipped with essential appliances, and natural light enters through the window beside the private entrance.

4.88 out of 5 average rating, 542 reviews

Private Studio Comfort with a view

Family-friendly home rentals with a pool

5 out of 5 average rating, 31 reviews

A serene outdoor patio area features a table complemented by comfortable chairs, surrounded by lush greenery. A small waterfall pond is visible in the background, framed by tall trees and a clear sky, offering a peaceful natural setting.

Home in Larkspur

Forest Retreat, 2 floors, 3 bedrooms w/Hot Tub Spa

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

4.91 out of 5 average rating, 232 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

Superhost

A spacious living area features grey leather seating arranged around a glass coffee table. A modern electric fireplace spans the wall beneath a vibrant piece of artwork. Large windows provide natural light and views of the surrounding landscape.

Apartment in Colorado Springs

4.84 out of 5 average rating, 62 reviews

2BD Luxury Condo, Cocktail Lounge, Beautiful Views

4.88 out of 5 average rating, 131 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