Vacation rentals in Woodland Park

4.93 out of 5 average rating, 156 reviews

Home in Woodland Park

Little Woody's Hideaway-(4)DownTown,HotTub,pets

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 at the hideaway for all your adventures!

4.97 out of 5 average rating, 197 reviews

Cabin in Woodland Park

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.

4.88 out of 5 average rating, 383 reviews

Cabin in Woodland Park

Cabin In Woodland Park with Pikes Peak View

Our Cabin was built in 1947, it is a bit of Country but was recently updated with a modern flair with cool interior barn doors and decor, but we kept the nuts and bolts of the 1940's design. It has an incredible view of Pikes Peak, Woodland Park has many restaurants, family-friendly activities. Only 25 Minutes to Colorado Springs. The Cabin is good for couples, solo adventurers, and furry friends. The cabin is cute and cozy and located just off Main Street in Woodland Park. License # 329434

Guest suite in Woodland Park

The exterior of the mountain home is illuminated by warm string lights, creating a tranquil ambiance. The structure features multiple levels and decks surrounded by tall trees, blending harmoniously with the natural surroundings. The nighttime sky adds depth to the serene setting.

4.99 out of 5 average rating, 255 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.

4.99 out of 5 average rating, 105 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

The sleeping loft features a cozy setup with plush cushions and pillows against wooden walls. A soft carpet enhances comfort, while built-in storage is visible along the edges. Soft lighting illuminates the space, creating a restful atmosphere for overnight stays.

4.93 out of 5 average rating, 516 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 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 🤗

4.99 out of 5 average rating, 324 reviews

The cabin is nestled among tall trees, showcasing an inviting deck with outdoor seating. Soft lighting highlights the structure, while the surrounding dark woods enhance the sense of seclusion. A small fire pit area is visible in the backyard, creating a serene outdoor ambiance.

Cabin in Divide

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

Bungalow in Woodland Park

A modern bathroom features a walk-in shower enclosed by glass, accented with a patterned tile strip. A stone countertop holds a rectangular sink, complemented by a set of neatly stacked towels. Natural light enters through two small windows, illuminating the clean, neutral tones.

4.93 out of 5 average rating, 134 reviews

Remodeled Bungalow in the heart of downtown WPK.

Interior designers newly remodeled craftsman bungalow in the heart of downtown WPK. Professional pictures coming soon. 2 king bedrooms/2 full bath home within walking distance to restaurants, shopping & Dino museum. Large city lot with patio, lots of trees & great views. Wood burning fireplace anchors the large living room. Original hardwood floors. Comfortable beds & furnishings. Well stocked kitchen. Woodland Park is surrounded by the million acre Pike National Forest.

The exterior of the A-frame cabin is surrounded by tall trees, featuring a wooden deck with two adirondack chairs. A large triangular window adorns the front, complemented by a welcoming entrance door, emphasizing the cabin's charming architecture.

4.97 out of 5 average rating, 137 reviews

A-frame, Tiny home, Hot tub, Sleeps 4!

Kick back and relax in this stylish tiny home A-frame on 2 acres for a romantic getaway or time with your family. • Hot tub • Sleeps 4 • Indoor fire place & outdoor propane fire pit • Fully stocked coffee bar provided • Board games • Off-road trails & rentals in town all year • 15 minutes to Pikes Peak Entrance • 25 mins to Cave of the Winds • 35 mins to Garden of the Gods • Secluded & outside of city limits, yet minutes to town • 45 minutes to CO Springs Airport

4.87 out of 5 average rating, 120 reviews

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

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.

4.88 out of 5 average rating, 257 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!

A striking natural landscape features towering red rock formations surrounded by a blanket of snow, showcasing the rugged beauty of the area. Lush evergreen trees add vibrant greenery to the scene, while the cloudy sky enhances the tranquil atmosphere of the outdoor setting.

4.9 out of 5 average rating, 299 reviews

Spacious Tiny House

Unplug from the hustle and bustle and wake up to blue skies, rustling leaves and crisp mountain air! But don't worry about roughing it-our tiny home is strategically situated near local shops, eateries, and markets, ensuring you have everything you need just a stone's throw away. After a day of exploring rugged trails and capturing awe-inspiring vistas, unwind in a space that boasts modern comforts like hot showers, comfortable bedding, and Wi-Fi.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Woodland Park vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Woodland Park's top sights

Rocky Mountain Dinosaur Resource Center78 locals recommend

Hungry Bear32 locals recommend

BierWerks33 locals recommend

Fusion Japan29 locals recommend

CAFE LEO18 locals recommend

Swiss Chalet Restaurant5 locals recommend

House rentals in Woodland Park

The bedroom features a spacious bed with light bedding, accompanied by a bedside table and lamp. Wall art and mirrors add interest. French doors connect the room to a cozy living area, illuminated by natural light from the nearby windows.

4.88 out of 5 average rating, 401 reviews

Downtown Victorian Home, Fenced In Yard with Grill

A two-story home is presented with a mix of brick and siding. A driveway leads to a one-car garage. Lush green grass frames the front, with trees providing shade. The clear blue sky enhances the inviting exterior, which features a staircase leading to the entrance.

4.87 out of 5 average rating, 254 reviews

Beautiful Mountain

Home in Old Colorado City

A modern living room is highlighted by a sleek leather sofa adorned with colorful cushions. Natural light enters through two windows with yellow curtains. A glass coffee table sits atop a vibrant rug, with an inviting view of the open kitchen in the background.

4.91 out of 5 average rating, 228 reviews

Modern, In the Heart of Old Colorado City!

Home in Old Colorado City

A single-story home is depicted with a welcoming front porch. A neatly fenced yard surrounds the property, featuring vibrant greenery and mulch landscaping. The main entrance is framed by two windows, providing natural light, while a pathway leads from the sidewalk to the front door.

4.91 out of 5 average rating, 280 reviews

Sienna Corner House | 2 BR/1 BA | in heart of OCC

A charming yellow cottage features a welcoming front porch with a small table and two chairs. The landscaped yard is highlighted by stones and borders, while a wooden fence provides privacy. Nearby trees add to the serene outdoor setting.

4.87 out of 5 average rating, 404 reviews

Downtown Cottage | Hot Tub | Pets | Fire Pit

Home in Downtown Colorado Springs

A spacious bedroom is highlighted by a large bed with crisp white bedding. Flanking the bed are two nightstands with blue lamps. A modern artwork piece hangs above the bed, complementing the muted blue wall. Natural light filters through the nearby window.

4.82 out of 5 average rating, 468 reviews

Downtown | Hot Tub | Big Backyard | Pet Friendly

Home in Old Colorado City

A cozy outdoor seating area is set on a wooden deck, featuring a round black table surrounded by four chairs with orange cushions. A fire pit sits nearby, offering warmth and ambiance. Lush trees and a wooden fence create a private and inviting atmosphere.

4.91 out of 5 average rating, 235 reviews

Spacious home walkable to Old Colorado City

A cozy bedroom features a spacious bed adorned with a textured blanket in warm tones. Two bedside tables with simple lamps are positioned on either side. A woven headboard adds an organic touch, while natural light brightens the inviting space.

4.99 out of 5 average rating, 100 reviews

Downtown Home Smart Car Plugin - 1 block from CC

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Other great vacation rentals in Woodland Park

Home in Green Mountain Falls

A hot tub is situated on a balcony, surrounded by lush trees and overlooking a mountainous landscape. The water is bubbling gently, and blue skies with scattered clouds provide a bright backdrop.

4.92 out of 5 average rating, 151 reviews

Pet friendly Newly remodeled Mountain get-a-way!

4.77 out of 5 average rating, 144 reviews

A vibrant street scene showcases a red motorcycle parked in front of a brick building with yellow awnings. American flags adorn the upper facade, adding to the inviting atmosphere of the town. The area appears well-maintained, with a fenced seating area visible on the sidewalk.

Cabin in Cripple Creek

Quiet Mountain Comfort 5 Bedrooms

4.97 out of 5 average rating, 195 reviews

A saltwater hot tub is positioned on a covered deck, offering an expansive view of the surrounding forest and mountain landscape. The tranquil water reflects the sky, while lush greenery and distant peaks create a serene backdrop.

Cabin in Florissant

Mydnyt Mtn Cabin w/Loft Private Hot Tub/No Chores

4.94 out of 5 average rating, 148 reviews

A wooden cabin is nestled among green pine trees, featuring a spacious wrap-around deck illuminated by soft lighting. The surrounding landscape showcases rolling hills and mountain views, while a pathway leads up to the cabin.

Cabin in Cripple Creek

Monarch Landing, A Cozy Cabin w/360 Mountain Views

4.92 out of 5 average rating, 567 reviews

Cabin in Florissant

☀Cabin with Mtn Views☀ A-Frame Nature Getaway

4.91 out of 5 average rating, 431 reviews

5BR Retreat w/ Hot Tub, Gym, & Cheyenne Mtn Views!

Condo in Colorado Springs

4.88 out of 5 average rating, 149 reviews

Getaway Condo: Spacious + View + Laundry + Quiet

A warm living area features a comfortable tan sofa and a modern fireplace, providing a cozy focal point. A chess table is positioned nearby, with sunlight illuminating the space. In the background, a dining area is visible, leading to an open layout that enhances connectivity.