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Vacation rentals in Woodland Park

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Top-rated vacation rentals in Woodland Park

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Top guest favorite

A panoramic view showcases snow-capped mountains rising majestically above a densely wooded landscape. Tall evergreens dominate the foreground, contrasting beautifully with the clear blue sky and distant peaks.

Cabin in Woodland Park

4.98 out of 5 average rating, 113 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.

The living area features a combination of comfortable seating, including a grey couch and two blue accent chairs. Natural light filters through skylights, illuminating the stone accent wall. A central coffee table is positioned on a patterned rug, creating a cozy atmosphere for relaxation.

Chalet in Woodland Park

4.93 out of 5 average rating, 107 reviews

Blissful Mountain Escape: Wi-Fi>HotTub>Fenced Yard

Escape the mundane life cycle into this Majestic, Cozy Mountain escape, nesting within reach of several Ski Slopes, Scenic Hiking/Biking trails, or just unwinding admits nature, A perfect basecamp for relaxing after nature adventures! Perfect for a Romantic Couple’s Retreat, Anniversaries, or a true Family Getaway centrally located in Woodland Park (City Above the Clouds) with convenient reach to Pikes Peak Rocky Mountain Range, 30 mins to Garden of the Gods, and 13 minutes to Manitou Springs.

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.

Tiny home in Woodland Park

4.93 out of 5 average rating, 538 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.

Cabin in Woodland Park

4.98 out of 5 average rating, 209 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.

Top guest favorite

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

4.99 out of 5 average rating, 345 reviews

Rainbow Trail A-Frame Hot Tub |Firepit| StarGazing

This recently renovated A-frame cabin is nestled on 2 acres of tranquil, forested land surrounded by aspen and pine trees — the perfect mountain escape. Unwind in the private hot tub, warm up by the cozy wood-burning stove, or gather around the outdoor fire pit for a night under the stars. Plus, with the addition of our Star Gazing Net in June 2025. Near Divide, Florissant, and Woodland Park, 45-minute drive from Colorado Springs, 1.5 hours from Breckenridge skiing, and 2 hours from (DIA).

Top guest favorite

A mountain home is set among Ponderosa pine trees, featuring a spacious deck with outdoor seating. The lower level has large windows allowing for views of the surrounding nature. The well-maintained lawn and landscaped area add to the inviting atmosphere of the property.

Guest suite in Woodland Park

4.99 out of 5 average rating, 263 reviews

Private Guest Suite w/Trees & Awesome Peak Views

Picture-perfect Pikes Peak views from your living room, bedroom, and covered patio of this stunning Colorado mountain home's guest suite with a classic Colorado feel. The suite includes the entire walk-out lower-level of our home. It is private, separate, and has its own entrance. With a full kitchen and central location, this is the perfect base-camp for a Colorado get-away; however, with the Ponderosa Pine, Aspen, and hiking trails right up the street, you may never want to leave.

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.

Cabin in Woodland Park

4.98 out of 5 average rating, 335 reviews

Magical A-Frame w/in Nat'l Forest-Firepit+MtnViews

►Escape to a secluded a-frame amidst 1+ million acres of pristine national forest ►Hike a 1.5 mile private trail just out your back door ►Unwind by the crackling fire pit under a star-filled sky ►Designed by boutique NYC interior design firm ►Complimentary organic local coffee, beer, and healthy snacks ►Prepare gourmet meals in the chef's kitchen ►Stocked with: board games, puzzles, books, yoga mats, and more ►Cozy up next to the inviting wood-burning stove ►High-end mattress and bedding

Top guest favorite

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.

Tiny home in Woodland Park

4.99 out of 5 average rating, 119 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

Top guest favorite

The exterior view of the home features a stone fire pit surrounded by seating, with flames flickering warmly in the evening. Soft lighting highlights the structure, while tall trees stand in silhouette against a night sky.

4.99 out of 5 average rating, 182 reviews

Colorado Luxury Retreat-Mtn View, Hot Tub & Sauna

Welcome to your 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 panoramic views of Pikes Peak that will take your breath away. With a magnificent 1200 sf patio and access to private walking trails, this space has everything you need for a peaceful and rejuvenating vacation or retreat -- a hotel penthouse experience on ground level. The hot tub is filled with fresh water for every guest.

Top guest favorite

The cabin is nestled among tall, green trees, surrounded by a natural landscape. A spacious deck extends from the front of the cabin, providing an outdoor area. The dirt road leading to the cabin is visible, indicating a secluded mountain retreat.

Cabin in Divide

4.99 out of 5 average rating, 343 reviews

Black Ridge Cabin|Private Hot Tub &Forest Retreat

The Black Ridge Cabin - Your mountain escape! 🗻Tucked in Colorado’s STUNNING Pikes Peak region 🛏️ Cozy 2BR w/queen beds on 1 private acre 🌌 Secluded hot tub under the stars 🔥 Indoor Fireplace + fast Starlink Wi-Fi 🍳 Stocked kitchen + washer/dryer 🌲Near hiking trails & hillside access with fenced yard 🚗 20 mins to Woodland Park, 2 hrs to DIA 🚶‍♂️ Walk to scenic Burgess Reservoir (no lake access) 🔥 Fire pit, outdoor dining, forest views 🅿️ Covered carport + driveway parking

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.

Cabin in Woodland Park

4.87 out of 5 average rating, 124 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 bright and welcoming living area features a light-colored sofa with a cozy yellow throw pillow. A large TV is mounted on the wall opposite a comfortable armchair. Sunlight streams through multiple windows, illuminating a view of the dining area beyond.

Tiny home in Woodland Park

4.87 out of 5 average rating, 267 reviews

Sunny Tiny Haven | BBQ, Fresh Vibes & Peak Views

🏔️ Tiny Oasis | Serenity & Pikes Peak Views Await! 🌲 As featured on Tiny House Expedition, this charming retreat in Peak View Park offers the perfect mix of cozy cottage vibes and woodland tranquility. Nestled on a private drive with towering trees and wildlife, enjoy secluded porch views, BBQ nights, and breathtaking Pikes Peak scenery. After skiing, unwind with cocoa and soak in the peaceful mountain atmosphere. 💫 Book now for your perfect escape!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Woodland Park vacation rentals

Laptop-friendly workspace

Woodland Park house rentals

Top guest favorite

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.

Home in Woodland Park

4.97 out of 5 average rating, 116 reviews

Purple Mountain Chalet, Views, Hot Tub, Game Room

The living area features a stone fireplace, providing a central focal point. Two light-colored sofas are arranged around a wooden coffee table on a patterned rug. A large window allows natural light to fill the room, with a view of the outdoor space visible.

Home in Woodland Park

4.95 out of 5 average rating, 226 reviews

Pinecone Cottage | Hot Tub | Fire Place | Dogs OK

Top guest favorite

A serene outdoor landscape is visible, featuring green grass and native plants, with a gravel path meandering through the scene. Majestic snow-capped mountains rise in the background, framed by tall pine trees. A fire pit surrounded by chairs and a barbecue grill is positioned to the right.

Home in Woodland Park

5 out of 5 average rating, 67 reviews

Mountain Glen Vista! License # 331228

Top guest favorite

Home in Woodland Park

4.94 out of 5 average rating, 101 reviews

Pikes Peak View~Hot Tub~Theater~Game Room~Firepit

Top guest favorite

The exterior of a modern two-story guest house is shown, featuring large windows and a combination of light and dark materials. The structure is situated amidst tall pine trees on a gravel driveway, with a single carport located beneath the upper level.

Home in Colorado Springs

5 out of 5 average rating, 161 reviews

Private Guest House in the Forest

A warm living area features wooden flooring and large windows providing views of the outdoors. A stone wood stove stands prominently, accompanied by a comfortable seating arrangement. Decor includes rustic elements, with a coffee table at the center, enhancing the inviting ambiance.

Home in Woodland Park

4.88 out of 5 average rating, 137 reviews

Bear Paw-Family/Pet friendly/private/HOT TUB!

A bright dining area is framed by large landscape windows, offering views of snow-covered mountains and trees. A sturdy wooden table with light-colored chairs is positioned near the windows, complemented by vibrant potted plants. A telescope is visible nearby, enhancing the space's connection to nature.

Home in Cascade-Chipita Park

4.88 out of 5 average rating, 104 reviews

Romantic Home w/ Hot Tub, Mt. Views & Art

An outdoor deck area is furnished with comfortable seating and a glass-top table. The surrounding lush landscape features a spacious fenced-in yard and tall trees, offering a serene setting for relaxation and enjoyment.

Home in Green Mountain Falls

4.94 out of 5 average rating, 225 reviews

Beautiful mountain getaway with hot tub!

Other great vacation rentals in Woodland Park

Top guest favorite

A comfortable living area is presented with a pair of brown sectional sofas adorned with patterned yellow pillows. A round coffee table sits at the center, topped with a decorative tray. Natural light filters through two windows, complemented by light curtains.

Home in Woodland Park

5 out of 5 average rating, 21 reviews

Cozy Mountain Retreat ~Hot Tub ~Fire Pit ~Grill

Top guest favorite

The exterior of the A-frame cabin is surrounded by tall pine trees, featuring a rustic wooden facade and a green roof. A small porch area is visible with sliding doors, and a gravel yard provides space for outdoor activities.

Chalet in Woodland Park

5 out of 5 average rating, 29 reviews

Tackle Mtn Lodge: Relax, Activities, No Chores!

An aerial view of a mountain cabin surrounded by lush trees, with a spacious wrap-around deck visible. The structure boasts a dark roof and is set against a backdrop of distant mountains and clear blue skies.

4.88 out of 5 average rating, 34 reviews

Ana-log Cabin: cozy retreat with mid-century hygge

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.

Cabin in Woodland Park

4.92 out of 5 average rating, 194 reviews

Rustic cabin charm w/ hot tub, arcade basketball

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.

Cabin in Woodland Park

4.93 out of 5 average rating, 46 reviews

Woodland Park Scandi Cabin, Mtn Views & Hot Tub

Top guest favorite

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.

Cabin in Florissant

4.98 out of 5 average rating, 58 reviews

New! A-Frame w/ Hot Tub + Stargazing Dome

Top guest favorite

The exterior of a two-story apartment is shown, featuring a mixture of wooden and stone elements. Dense pine trees stand prominently, providing natural framing. A stone wall borders the property, while a balcony extends across the upper level, offering potential outdoor relaxation areas.

Vacation home in Woodland Park

4.98 out of 5 average rating, 50 reviews

Cozy couples get away with view of Pikes Peak

Top guest favorite

A modern cabin exterior is framed by tall pine trees, featuring a dark wood façade and large windows. Two bright red Adirondack chairs are positioned on a gravel area in front, inviting relaxation amidst the natural surroundings.

Cabin in Florissant

4.97 out of 5 average rating, 193 reviews

Whimsical Dreams Cabin | Firepit | Kids Fort

Quick stats about vacation rentals in Woodland Park

Total rentals
200 properties
Nightly prices starting at
G$2,089 GYD before taxes and fees
Total number of reviews
16K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
120 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Woodland Park?
Yes! Work meets play with ease at over 120 vacation rentals in Woodland Park featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Woodland Park?
Four-legged friends are welcome in Woodland Park. Choose from more than 70 vacation rentals for guests traveling with pets.
How much does it cost to stay in tiny house rentals in Woodland Park?
Experience the best of Woodland Park with our tiny house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do private suite rentals in Woodland Park have wifi?
Absolutely! We offer over 10 private suite rentals with wifi in Woodland Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodland Park have a gym?
Absolutely! We offer over 10 house rentals with a gym in Woodland Park. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Woodland Park have self check-in?
Absolutely! We offer over 30 cabin rentals with self check-in in Woodland Park. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodland Park have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Woodland Park. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Woodland Park?
Woodland Park has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore