Family-friendly holiday rentals in Woodland Park

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, 256 reviews

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

An A-frame cabin is nestled among vibrant autumn foliage, with golden leaves framing the structure. The entrance features a welcoming porch adorned with wooden railings, and large windows provide glimpses of the interior. The surrounding trees create a serene, natural setting.

4.91 out of 5 average rating, 102 reviews

Woodland Park Scandi Cabin, Mtn Views & Hot Tub

Welcome to our Scandinavian-inspired cabin in Woodland Park, CO, just minutes from Pikes Peak. This cozy retreat combines minimalist design with comfort, offering stunning mountain views, wildlife sightings, & easy access to scenic trails. Enjoy a fully equipped kitchen, serene living space, & peaceful setting perfect for relaxation or a romantic getaway. Embrace the beauty of nature and Scandinavian warmth, making this cabin the ideal place to unwind, explore, & experience Colorado’s outdoors.

The living area showcases a pair of comfortable gray sofas arranged around a coffee table. A large television displays a virtual fireplace, creating a cozy ambiance. A light fixture casts a warm glow, and a dining area with a wooden table provides additional seating.

4.92 out of 5 average rating, 190 reviews

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!

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, 601 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 secluded cabin is set among tall trees, featuring multiple outdoor decks and a covered porch area. The structure showcases wooden siding and a chimney, with lush green grass leading up to it, inviting a sense of tranquility and connection to nature.

4.97 out of 5 average rating, 150 reviews

Design Cabin Private Ridge Hike Stargazing Hot Tub

Looking for a peaceful escape near Woodland Park? This private cabin is tucked away in nature with a hot tub, private trail, and total quiet. Spend your days exploring and your evenings soaking under the stars. Perfect for a last-minute getaway, romantic stay, or simply getting out of the city. ► Hot tub for stargazing in dark-sky country ► Cozy wood-burning stove for warm, relaxing evenings ►Fully equipped chef’s kitchen for gourmet meals ►Thoughtfully designed by a boutique NYC design firm

4.89 out of 5 average rating, 318 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

►Location: Short drive to CO Wolf + Wildlife Ctr, award-winning Paradox Beer Co, Fossil Beds, Lake George, Mueller State Park, Pikes Peak, Garden of the Gods ►OUTDOORS: Nearby hiking, biking, snowshoeing, horseback riding, cross country skiing, rock climbing, rafting ►DINING/CASINO: Short drive to Cripple Creek + Woodland Park ►YARD: picnic table, grill, yard games, barrelwood SAUNA + firepit ►FAMILY FRIENDLY: Pack n play, high chair, monitors, toys + more! ►Equipped Kitchen ★WAFFLE MAKER★

4.95 out of 5 average rating, 225 reviews

Riverside Retreat: Sauna, Hot Tub & Fireplace

With a river in the backyard next to the private hot tub and sauna, what more could you need? If you love watching local wildlife, listening the sound of the creek, and relaxing on a luxurious back patio that’s perfect for all seasons, then RiverHouse South by Forest & Peak Retreats is for you! Enjoy the full amenities of a kitchen stocked with a curator’s touch, heated towel rack, remote control gas fireplace, top-to-bottom remodel. Book RiverHouse South, by Forest & Peak Retreats, today!

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.

4.98 out of 5 average rating, 125 reviews

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.

A cabin stands surrounded by tall trees under a starry night sky. Warm light spills from the windows, illuminating the path leading to the front door. A wood firepit is visible in the foreground, contributing to the tranquil outdoor setting.

4.86 out of 5 average rating, 126 reviews

Dark Sky Views - Firepit - Sauna - Grill - Fishing

Our cabin is nestled on an acre near Pikes National Forest with access to fishing, hiking & adventure all around. With all the amenities, 45min to Colorado Springs, 10 min to the S. Platte River Dream Stream, world class fishing, Mueller State Park, Pike's Peak & ATV-ing. A tranquil location in the woods w/ incredible views of the Milky Way, evening fires outdoors, great times w/ friends on the deck, hot coffee, wildlife, relaxation in the sauna, you’re sure to unwind from the daily grind.

The exterior of a charming A-frame cabin is showcased, featuring a wooden deck with a railing. Large floor-to-ceiling windows allow ample natural light into the space, providing a view of the surrounding trees and outdoor seating area.

4.92 out of 5 average rating, 677 reviews

☀Cabin with Mtn Views☀ A-Frame Nature Getaway

★Location: Minutes to CO Wolf + Wildlife Ctr, award-winning Paradox Beer Company, Fossil Beds, Lake George, Mueller State Park. Short Drive to Pikes Peak, Garden of the Gods ★OUTDOORS: Nearby hiking, biking, snowshoeing, horseback riding, cross country skiing, rock climbing, white water rafting ★DINING/SHOPS: Short drive to Woodland Park & Historic Manitou ★VIEWS of the Continental Divide from the large back porch & bedroom balcony ★Grill + Firepit ★Brand new comfy beds ★Equipped Kitchen

Tiny home in Woodland Park

A cozy living room features a brown leather sofa and a handmade wooden table. Natural light floods the space through large windows, illuminating a relaxing nook with patterned poufs and a guitar hung on the wall. Outdoors, a porch with rocking chairs offers a view of the surrounding trees.

4.99 out of 5 average rating, 166 reviews

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

4.96 out of 5 average rating, 139 reviews

The living room features vaulted ceilings with large windows that provide natural light and views of the surrounding trees. A comfortable seating area includes spacious recliners and a coffee table, complemented by a cozy area rug. A flat-screen television is mounted above the fireplace.

Chalet in Woodland Park

Aspen Grove Chalet | A Modern Alpine Retreat

Discover a peaceful home base for your Pikes Peak adventures. Aspen Grove Chalet is a thoughtfully designed, multi-level mountain home that invites the outdoors in. Experience quiet mornings watching local wildlife and sunset views through the pines—all while staying minutes from the heart of Woodland Park. As a pet-loving household, we are proud to offer a truly pet-friendly experience with no extra fees, ensuring you and your companions feel right at home.

Popular amenities for Woodland Park family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The image showcases a breathtaking view of snow-capped mountains under a soft glow, framed by trees in the foreground. The varying shades of green and the snow highlight the majestic peaks, creating a serene and tranquil landscape.

4.97 out of 5 average rating, 161 reviews

Purple Mountain Chalet, Views, Hot Tub, Game Room

Cabin in Green Mountain Falls

A charming blue cabin features a triangular roof and a spacious balcony, surrounded by pine trees. Two kayaks are securely mounted on the side, and the entryway is framed by flower decorations. The backdrop showcases a scenic mountain view beneath a clear blue sky.

4.92 out of 5 average rating, 196 reviews

Cabin in the Woods*Hot Tub*Fireplace*Foosball

The exterior of a multi-story cabin features a mix of natural stone and wood siding, surrounded by trees. A set of stairs leads to the main entrance, while large windows provide views of the surrounding landscape. The welcoming design blends seamlessly with the forested setting.

4.97 out of 5 average rating, 116 reviews

Serene Mountain Retreat: Fireplace, Hot Tub, Views

Cabin in Green Mountain Falls

A spacious outdoor area features a covered gazebo with seating, surrounded by a landscaped yard. Decorative planters and a water feature with stones add a natural touch. The exterior of the home is adorned with large windows and a bright red door, inviting guests in.

4.94 out of 5 average rating, 125 reviews

Pub - Hot Tub - Fire Pit

A spacious living area features a ceiling fan and large sectional sofa arranged around a coffee table. The floor is wood-like, complemented by an area rug. Natural light enters through multiple windows, and an adjacent dining area is visible in the background.

4.86 out of 5 average rating, 114 reviews

Mountain Sanctuary - Family Retreat

4.98 out of 5 average rating, 267 reviews

Retreat at Mydnyt Mountain•Hot Tub•No Chores

4.98 out of 5 average rating, 196 reviews

Elwood A-frame | Hot tub | Fire Pit | Pike's Peak

A modern A-frame cabin is nestled in a snowy landscape, showcasing a spacious deck and a luxurious hot tub. Nearby, a geodesic dome offers a unique stargazing experience. The backdrop features a starry sky, enhancing the serene mountain setting.

4.98 out of 5 average rating, 126 reviews

Modern A-Frame w/ Hot Tub + Stargazing Dome

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 173 reviews

The exterior of the cozy cabin is shown with a welcoming door framed by warm outdoor lights. Two metal chairs and a small table are placed on the patio, scattered with autumn leaves. The surrounding trees hint at a tranquil wooded setting.

Cabin in Cripple Creek

Lucky Llama A-Frame|Views |Fireplace|Dogs Welcome!

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, 268 reviews

Quaint and Historic Studio Cabin

Two colorful Adirondack chairs are positioned on a gravel path overlooking a serene lake surrounded by rolling green hills and trees. The sky features varying shades of blue and gray, hinting at a tranquil atmosphere that invites relaxation.

4.93 out of 5 average rating, 88 reviews

Modern Western - Lake, Spacious, Family

4.98 out of 5 average rating, 181 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, 175 reviews

A rustic cabin constructed from logs is nestled among tall trees, featuring a green metal roof. A hammock hangs between two trees in the foreground, inviting relaxation in the natural setting. The stone chimney adds character to the cabin's cozy appearance.

Cabin in Divide

Rustic, Comfy Colorado Cabin on 40 Wooded Acres

4.99 out of 5 average rating, 427 reviews

The A-frame cabin is illuminated by warm string lights, showcasing its inviting façade against a backdrop of a colorful sunset. A private hot tub is positioned beside the cabin on a stone patio, surrounded by greenery and natural setting.

Cabin in Divide

Rainbow Trail A-Frame Hot Tub |Firepit| StarGazing

Superhost

The entrance of the cabin is displayed, featuring a welcoming red door adorned with a wreath. A wooden bench with two cushions sits on a stone pathway, surrounded by trees and planters, creating an inviting outdoor space.

4.87 out of 5 average rating, 430 reviews

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.

5 out of 5 average rating, 209 reviews

Off-grid, Earthen home in the forest!

Family-friendly home rentals with a pool

Superhost

A spacious living area is furnished with a leather sofa and two easy chairs adjacent to a wooden accent table. Floor-to-ceiling windows offer expansive views of the surrounding landscape, while sliding glass doors provide direct access to the L-shaped terrace.

Flat in Colorado Springs

4.55 out of 5 average rating, 74 reviews

Overlooking Mountain Views | Terrace | Pool access

Superhost

Home in Manitou Springs

5 out of 5 average rating, 3 reviews

4 Bedrm Home w/Seasonal Pool in Manitou Springs

4.98 out of 5 average rating, 45 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

4.92 out of 5 average rating, 273 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, Pool, Bball court

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.

4.91 out of 5 average rating, 149 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

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.

4.88 out of 5 average rating, 133 reviews

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, 162 reviews

Rustic Historic Colorado Mountain Cabin Pikes Peak