Family-friendly holiday rentals in Woodland Park

Place to stay in Woodland Park

A hot tub is positioned on a deck, offering views of lush green trees and distant mountains under a partly cloudy sky. The bubbling water invites relaxation while the natural surroundings create a serene atmosphere.

4.99 out of 5 average rating, 163 reviews

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.

An A-frame cabin exterior is visible at dusk, with a sloping black facade contrasting against the colorful sunset. A neatly stacked pile of firewood is situated in a circular holder on the deck, alongside a potted plant for a touch of greenery.

4.98 out of 5 average rating, 403 reviews

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

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, 619 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 brightly colored cabin is illuminated by string lights, creating a warm ambiance at night. A patio area is visible, featuring outdoor seating that invites relaxation. The front door is framed by a welcoming entryway, accentuated by decorative shutters.

4.98 out of 5 average rating, 240 reviews

Farmhouse-In The Heart of Town-Dogs OK-Hot Tub!

Go back in time in a 1930's Farmhouse cabin near Pikes Peak. Great location, 2 blocks from downtown and new hot tub! Walk to coffee shops, restaurants & parks. Enjoy the outdoor fresh air, hiking & fishing. Short drive to Pikes Peak & many other must see sites! Fully stocked kitchen with fun retro appliances. Dog friendly with a fenced in backyard. Enjoy an evening around the outdoor fire pit or indulge in relaxation & enjoy the remote fireplace in the bedroom. WIFI, Smart TV's and plush bed.

4.91 out of 5 average rating, 693 reviews

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.

Cabin in Florissant

☀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

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, 180 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

Cabin in Cascade-Chipita Park

4.99 out of 5 average rating, 256 reviews

Serene Riverside Cabin w/ 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!

4.97 out of 5 average rating, 245 reviews

Cabin in Florissant

Whimsical Dreams Cabin | Firepit | Kids Fort

Unwind in this modern cozy cabin in the Colorado woods! Recently remodeled inside and out. Recently added is a Kids Fort right in the backyard! Come to fish at the local lake, hike hundreds of nearby trails, play the slots at Cripple Creek, and end your day relaxing on the secluded back deck. In the nearby town of Woodland Park, you can do your grocery shopping, have a beer, or grab a coffee and homemade donut! Or take the drive to Colorado Springs (50 minutes) to visit much more!

4.96 out of 5 average rating, 197 reviews

A-frame, Tiny home, Sauna, Hot tub, 3 acres!

Kick back and relax in this stylish 1965 A-frame tiny home on 2 private acres, perfect for a romantic getaway or family adventure. • Hot tub • Sleeps 4 • Barrel sauna • Electric fireplace & outdoor propane fire pit • Fully stocked coffee bar • Board games • 15 mins to Pikes Peak Entrance & the Wolf Sanctuary • 25 mins to Cave of the Winds • 35 mins to Garden of the Gods & Cripple Creek casinos • Private mountain setting, minutes to town • 45 mins to Colorado Springs Airport

The entrance of a cabin is framed by rustic wooden beams, with a green front door welcoming visitors. Two white Adirondack chairs are positioned on a stone patio, providing a place to relax. Surrounding trees display vibrant autumn colors, adding to the cabin's natural setting.

4.87 out of 5 average rating, 144 reviews

Cozy Mountain Cabin Retreat

Find yourself at this cozy cabin located just 8 minutes outside of historic Woodland Park. Enjoy your morning coffee with common sightings of wildlife. During the evening, enjoy fireplace gatherings under the stars on the wrap around private patio. This updated cabin is located close to popular attractions: Mueller State Park, Santa's North Pole, Cave of the Winds, Pikes Peak, Garden Of the Gods, gambling at Cripple Creek, fishing, hiking & biking trails, etc.

A comfortable seating area features a pair of brown leather sofas positioned around a low black metal table, with decorative pillows and a small plant on the table. A light-colored area rug is laid over warm wooden flooring, and a small lamp stands nearby.

4.86 out of 5 average rating, 227 reviews

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!

4.94 out of 5 average rating, 418 reviews

Cozy Tiny Cabin | Hot Tub + Pikes Peak Views

Welcome to Tiny Timber! Relax in the hot tub beneath the Colorado stars at this cozy tiny cabin in Woodland Park, the “City Above the Clouds.” This peaceful Rocky Mountain retreat is the perfect cabin near Pikes Peak and a great home base for exploring the area. Just minutes from Pikes Peak Highway, Manitou Springs, and Colorado Springs, you’ll enjoy adventure by day and a relaxing mountain getaway each evening.

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, 163 reviews

Purple Mountain Chalet, Views, Hot Tub, Game Room

The spacious living room features a large window that invites natural light, showcasing views of the outdoors. A wood-burning stove is complemented by a cozy blue couch, a coffee table, and patterned area rug. A television sits on the opposite wall, enhancing the welcoming ambiance.

4.98 out of 5 average rating, 136 reviews

Aframe, Hot Tub, Scenic Views, Firepit, Dogs YES

Superhost

A spacious bedroom featuring wooden beams and a stone fireplace, with a large window opening to a balcony. A comfortable bed is accented with a textured blanket and a decorative pillow. Natural light fills the room, creating a warm and inviting atmosphere.

4.83 out of 5 average rating, 112 reviews

*Tranquil Acres - Retreat, Outdoors, Camp, Cabin*

4.98 out of 5 average rating, 798 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.

Apartment in Divide

The Hideaway

5.0 out of 5 average rating, 437 reviews

Black Ridge Cabin|Private Hot Tub & Forest Retreat

A hot tub sits in an outdoor setting, surrounded by tall trees and natural landscapes. The water reflects the blue sky, creating a serene atmosphere. The space is designed for relaxation and enjoyment of the forest views.

4.91 out of 5 average rating, 229 reviews

Rustic cabin charm w/ hot tub, arcade basketball

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, 197 reviews

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

Cabin in Cascade-Chipita Park

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, 301 reviews

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

Family- and pet-friendly home rentals

An open concept kitchen and living area is displayed, featuring a large island with light granite countertops. Natural light floods in through tall windows, illuminating the space. The warm wood beams and ceiling fans add a welcoming touch to the modern decor.

4.92 out of 5 average rating, 135 reviews

The Downtown Nugget | Pikes Peak Base | BL 330900

Farm stay in Woodland Park

A single-story bunkhouse is nestled within a natural setting, featuring large sliding glass doors that open to a patio area. Comfortable seating is arranged outside, with potted plants adding greenery to the landscape. Surrounding pine trees enhance the woodland atmosphere.

4.99 out of 5 average rating, 173 reviews

Bunkhouse In The Pines

4.96 out of 5 average rating, 244 reviews

The exterior of the log cabin showcases rustic wooden siding and a welcoming entrance. A spacious deck with railings provides access to the main door, surrounded by trees and nature. The building features large windows and a unique round window, enhancing its charm.

Cabin in Florissant

Sunset Mountain Log Cabin Retreat - Upper Unit

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, 442 reviews

Cabin with Pikes Peak View in WP License#329434

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.

4.89 out of 5 average rating, 336 reviews

𓃵Moose Cabin𓃵 Sauna┃Firepit┃Woodstove┃Corn hole

A rustic log cabin with a green metal roof is surrounded by tall trees, partially covered in snow. A small porch area is visible, featuring seating arrangements and a grill. The cabin's natural wood exterior reflects its historic charm amidst a serene winter landscape.

4.96 out of 5 average rating, 337 reviews

Best Li'l Bunkhouse on 40 Wooded Acres

The living area features a comfortable gray sofa paired with a distinctive black wingback chair. A decorative coffee table is centered on a soft area rug, while elegant light fixtures hang above. Natural light pours in through clerestory windows, enhancing the airy ambiance.

4.96 out of 5 average rating, 227 reviews

Charming Mountain Retreat with private HOT TUB

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.

4.99 out of 5 average rating, 441 reviews

Rainbow Trail A-Frame Hot Tub |Firepit| StarGazing

Family-friendly home rentals with a pool

A lit hot tub is nestled on a spacious deck, surrounded by trees. Soft blue lights illuminate the water, and string lights hang overhead, creating a serene evening atmosphere. Furnished lounge areas are visible in the background, inviting relaxation.

4.94 out of 5 average rating, 258 reviews

Hot tub, mtn views, massage chair, & steam shower!

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!

4.98 out of 5 average rating, 130 reviews

An expansive home showcases a contemporary Southwestern design, surrounded by lush greenery. Large windows and multiple deck areas provide scenic views. An inset image reveals an indoor heated pool, framed by large windows that invite natural light and emphasize the tranquil indoor space.

Home in Colorado Springs

Hidden Gem⋆Heated Pool⋆Gorgeous Views⋆2.4 ac⋆AC⋆EV

Guesthouse 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, 161 reviews

Urban Float - Heated Indoor Pool/HotTub & Firepit

4.97 out of 5 average rating, 151 reviews

The covered deck features a spacious seating area with comfortable furniture and a large outdoor kitchen equipped with a grill and a 36” griddle. A smart TV is mounted on the wall, and patio heaters are positioned for warmth. The pool and hot tub are visible in the background.

Home in Colorado Springs

Staycation

Apartment in Colorado Springs

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.

4.92 out of 5 average rating, 296 reviews

Quite spacious Apt w/Game Table, Pool, Bball court

Superhost

A spacious living area features a comfortable dark sofa and two patterned armchairs surrounding a glass coffee table. Natural light fills the room through large windows, highlighting the open concept layout that connects to the dining area and kitchen in the background.

Townhouse in Colorado Springs

4.87 out of 5 average rating, 195 reviews

Resort-Style Townhome | Pool, Hot Tub & Gym Access