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.

FamilyIndoor spacesNearby

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, 198 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!

FamilyKitchenDecor

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, 404 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

FamilyKitchenHeating

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, 622 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 🤗

FamilyIndoor spacesSleep quality

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, 140 reviews

Aframe, Dogs YES, Hot Tub, Scenic Views, 2 decks

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.

Indoor spacesFamilyCheck-in

A shaded porch is highlighted with wooden rocking chairs facing scenic mountain views. The cabin's wooden exterior features log paneling and a stylish wall light. The expansive deck allows for easy transition between indoor and outdoor spaces.

4.98 out of 5 average rating, 141 reviews

Alpine Escape: Family-Friendly w/ Gorgeous Scenery

Escape to a stunning mountain retreat where families can relax, unplug, and create lasting memories. Breathe in the crisp alpine air as you sip coffee on the wraparound deck, while the kids enjoy the tree swing. This spacious cabin offers a full kitchen, cozy lounge areas, and a dedicated workspace. Explore scenic trails just minutes away, with Mueller State Park only 6 minutes from your door and Cripple Creek within 19 minutes. Your perfect family getaway starts here—learn more below!

Indoor spacesFamilyTV

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, 696 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

FamilyKitchenParks

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, 184 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

FamilyIndoor spacesLayout

4.97 out of 5 average rating, 302 reviews

Secluded Mountain Cabin: Hot Tub, Deck & Fire Pit

Escape to the Timber A-Frame, by Forest & Peak Retreats, where luxury meets the untamed spirit of the Rockies. Discover a blend of refined elegance and mountain allure in this magazine-worthy retreat. Crafted with meticulous detail, this stylish cabin offers a sanctuary of comfort and sophistication. Indulge in the hot tub under the vast sky, explore nearby trails, and cozy up to a movie in the vaulted living room by the fire. Your perfect mountain getaway awaits at the Timber A-Frame.

Indoor spacesFamilyBackyard

5.0 out of 5 average rating, 271 reviews

Home in Divide

Private Luxury Spa Retreat: Hot Tub, Sauna & Views

Welcome to your romantic and luxurious mountain retreat at Eagle Ridge! The Living Room is a stunning 1400 sf newly renovated home situated in a gated 43-acre property with stunning views of Pikes Peak and exclusive use of the huge 6 seat hot tub and custom-built sauna. With a large 1200 sf patio and access to walking trails on this private property, this space has everything you need for a peaceful and rejuvenating vacation retreat -- a hotel penthouse experience on ground level!

KitchenIndoor spacesParking

4.96 out of 5 average rating, 198 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

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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, 229 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!

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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, 164 reviews

Purple Mountain Chalet, Views, Hot Tub, Game Room

Indoor spacesFamilyHiking

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.

5.0 out of 5 average rating, 303 reviews

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

KitchenFamilyHot tub

4.91 out of 5 average rating, 196 reviews

Beautiful Cabin w/ Decks/Views/sauna/hot tub!

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The exterior of the cabin showcases rustic wooden logs and a welcoming front door. A pink picket fence surrounds the property, with landscaped pathways leading to the entrance. Warm porch lights illuminate the cabin, enhancing its cozy appearance amidst the surrounding trees.

4.97 out of 5 average rating, 237 reviews

Sugar Shack -1930's Cabin-Downtown & Dog Friendly

FamilyKitchenAmenities

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, 114 reviews

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

Indoor spacesFamilyParks

4.97 out of 5 average rating, 276 reviews

Into the Woods Aframe | Hot Tub | FirePit| 6 Acres

FamilyIndoor spacesView

4.98 out of 5 average rating, 208 reviews

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

Indoor spacesFamilyView

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.

4.9 out of 5 average rating, 231 reviews

Rustic cabin charm w/ hot tub, arcade basketball

FamilyKitchenBathroom

Family- and pet-friendly home rentals

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, 337 reviews

𓃵Moose Cabin𓃵 Sauna┃Firepit┃Woodstove┃Corn hole

Indoor spacesKitchenLong stay

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

Indoor spacesFamilyBathroom

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

KitchenFamilyLaundry

A cozy cabin is illuminated under a clear night sky filled with stars. Warm lighting accents the exterior, while a fire pit surrounded by wooden chairs offers a space for relaxation and gathering. The surrounding nature enhances the tranquil atmosphere.

4.95 out of 5 average rating, 213 reviews

Wayward Lodge| Hot Tub | Fire Pit | Secluded

Indoor spacesKitchenHot tub

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, 444 reviews

Cabin with Pikes Peak View in WP License#329434

Indoor spacesKitchenWalkability

4.91 out of 5 average rating, 102 reviews

Come to the Hideout! Hot Tub, Fire Pits & Views!

KitchenIndoor spacesNearby

4.95 out of 5 average rating, 111 reviews

The Cozy Pine • A/C • Hot Tub • Game Room • Views

Indoor spacesKitchenQuiet

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, 137 reviews

The Downtown Nugget | Pikes Peak Base | BL 330900

KitchenIndoor spacesSleep quality

Family-friendly home rentals with a pool

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!

Indoor spacesFamilyAmenities

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, 260 reviews

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

KitchenIndoor spacesBiking

4.98 out of 5 average rating, 132 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

FamilyKitchenAmenities

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

KitchenFamilyAccuracy

4.97 out of 5 average rating, 153 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

Indoor spacesFamilyCheckout

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

Indoor spacesFamilyPool

Townhouse in Colorado Springs

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.

4.87 out of 5 average rating, 195 reviews

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

FamilyIndoor spacesHot tub