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.

4.91 out of 5 average rating, 116 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.

Superhost

A cozy living room features a stone fireplace complemented by a wooden accent wall. A brown leather sofa is arranged with decorative pillows. A coffee table sits centrally, with a small plant adorning its surface. Natural light enters through nearby windows, enhancing the inviting setting.

4.77 out of 5 average rating, 382 reviews

Creekside Cottage - Close to Pikes Peak

Enjoy a picturesque mountain retreat - perfect for a romantic weekend. Tucked at the base of Pikes Peak, this peaceful cottage is the ideal Colorado escape. Just 20 feet from Fountain Creek, you’ll fall asleep to rushing water and wake to sunrise over Waldo Canyon. Includes all the amenities you need. Minutes from Pikes Peak, Garden of the Gods, Manitou Springs, and top trails and breweries, this property sits on a private 2-acres where you can relax, unwind, stargaze, and soak in the scenery.

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, 359 reviews

Modern Luxury Cabin with 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, 568 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 🤗

A charming cabin is nestled among tall pine trees, with a snow-covered landscape surrounding it. The house features a front porch with wooden railings, and natural stone accents are visible on the exterior. A clear blue sky is contrasted by fluffy clouds above.

4.99 out of 5 average rating, 170 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, 264 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, 288 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, 212 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

Home in Cascade-Chipita Park

A four-person hot tub is visible, featuring clear bubbling water under a blue sky. Surrounding trees provide shade, while distant mountains create a serene backdrop, enhancing the relaxing environment of this outdoor space.

4.97 out of 5 average rating, 104 reviews

Rhapsody in Blue

The hills are alive with the sound of music in Cascade, CO! Welcome to Rhapsody in Blue! Just like George Gershwin's quintessential masterpiece; Rhapsody in Blue, challenged contemporary notions by blending classical and popular music, Our Rhapsody in Blue seeks to do the same by blending classic architecture and modern aesthetics into a beautiful symphony of color, contrast, movement and sound. You must see it, and hear it, to believe it. We eagerly await your arrival at Rhapsody in Blue.

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, 116 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, 295 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, 123 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

4.96 out of 5 average rating, 281 reviews

Home in Colorado Springs

Lake~Paddleboards~Hot Tub~Firepit~BBQ

4.93 out of 5 average rating, 118 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

Cottage in Colorado Springs

A vibrant blue house features a private outdoor hot tub, shaded by a large umbrella. Comfortable seating areas are positioned nearby on the decking, surrounded by a tall wooden fence providing privacy and a green backdrop of trees.

4.98 out of 5 average rating, 205 reviews

The Loft House *Downtown*HOT TUB*A/C*Private House

4.92 out of 5 average rating, 529 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, 103 reviews

The chalet's A-frame structure is framed by tall pine trees, showcasing large windows that invite natural light. A gentle plume of smoke is rising from the chimney, indicating a warm interior. The outdoor deck offers a seating area for relaxation amidst a scenic mountain setting.

Cabin in Woodland Park

Dogs YES, Hot Tub, 2 Decks, Fireplace, Scenic View

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

4.99 out of 5 average rating, 171 reviews

A custom A-frame cabin is surrounded by tall pines, featuring a sloped roof and large glass windows. A spacious deck with steps leads to outdoor seating and a hot tub, while natural stone landscaping adds to the serene setting.

Cabin in Monument

Cozy A-Frame Retreat “Hot Tub”w-Views, Monument CO

4.98 out of 5 average rating, 290 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

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 243 reviews

A wooden sign labeled 'Blue Spruce' stands in front of a log cabin, surrounded by tall trees and natural greenery. The cabin features a green roof and large windows, allowing a view of the serene outdoor environment. A path leads from the sign to the entrance.

Cabin in Manitou Springs

Keithley Pines Blue Spruce Cabin

4.88 out of 5 average rating, 284 reviews

A circular wooden sauna sits on a raised deck surrounded by trees. Blue adirondack chairs are arranged around a fire pit with glowing flames. The natural setting creates a peaceful atmosphere for outdoor relaxation.

Cabin in Divide

𓃵Moose Cabin𓃵 Sauna┃Firepit┃Woodstove┃Corn hole

4.97 out of 5 average rating, 697 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

Flat in Old Colorado City

A spacious backyard features a fenced area with a children's climbing structure and outdoor dining space. Comfortable chairs are positioned around a grill, alongside a pebbled path leading through the yard, surrounded by greenery and trees.

4.93 out of 5 average rating, 508 reviews

★OCC Getaway★ Firepit, Grill, Backyard + Firestick

4.97 out of 5 average rating, 144 reviews

An inviting outdoor patio is illuminated by string lights, featuring a stone fireplace surrounded by comfortable seating. The scene includes several dark wooden chairs arranged around a fire pit, with trees adorned by lights creating a cozy ambiance against the night sky.

Cabin in Lake George

Dark Sky Stargazing from Firepit, Mountain Views

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, 412 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

Guest suite in Colorado Springs

A cozy studio space features a queen bed adorned with dark bedding. In the background, a kitchenette is equipped with modern appliances and open shelving. A unique wall art piece injects character, while warm lighting adds to the inviting atmosphere.

4.81 out of 5 average rating, 198 reviews

NO FEE - Unique Studio by UCCS, Grdn Gods, Dwntwn

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, 113 reviews

Urban Float - Private Heated Pool/HotTub & Firepit

4.92 out of 5 average rating, 240 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, 101 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, 31 reviews

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