Vacation rentals in Woodland Park

4.93 out of 5 average rating, 160 reviews

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!

4.88 out of 5 average rating, 383 reviews

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

A modern ceiling fan with wooden blades is centrally positioned in the space, suspended from a sloped ceiling. Natural light filters through the large window, highlighting the architectural details of the loft area.

4.94 out of 5 average rating, 240 reviews

"Luxury Mountain Retreat,Tiny Home Away from Home"

Who knew living tiny, could offer so much! Come experience it for yourself. This newly renovated home has one private bedroom with a queen size bed, loft area with two full memory foam beds (flat screens in each!). The house is fully equipped w/ appliances, toiletries, cooking accessories, and everything you need for a relaxing mountain getaway. It can accommodate up to 8 guests. Relax on one of the two patios, around the fire pit, or snuggle up for dinner and a movie on the 55" flat screen!

4.99 out of 5 average rating, 333 reviews

Cabin in Divide

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).

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, 257 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, 108 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, 519 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, 329 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

A cozy loft sleeping area features warm wood paneling and soft ambient lighting. A spacious bed is adorned with plush bedding and decorative pillows. Two windows allow filtered light, complementing the inviting atmosphere of the unique tiny home.

4.94 out of 5 average rating, 359 reviews

Boutique Tiny Home! HOT TUB & Pikes Peak Views

Welcome to Tiny Timber! A beautiful tiny house nestled in the stunning Rocky Mountains of Colorado! This tiny house is a marvel of modern efficiency, located in Woodland Park, the "City Above the Clouds." Come make this your home base for adventure - with a cute mountain town at your doorstep for all your conveniences. Woodland Park is only 20 minutes west of Colorado Springs, 15 minutes to Manitou Springs, 15 minutes to Pikes Peak Highway, and 20 minutes to Florissant.

Superhost

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.

Bungalow in Woodland Park

4.93 out of 5 average rating, 136 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, 139 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

Superhost

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, 120 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.

Vacation rentals for every style

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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

Other great vacation rentals in Woodland Park

Superhost

A modern kitchen is displayed with sleek cabinetry and a large island featuring a granite countertop. Stainless steel appliances include a refrigerator and double ovens. Natural light enters through a door leading to the outdoors, complemented by neutral-toned tile flooring.

4.83 out of 5 average rating, 77 reviews

Mountain Sanctuary - Family Retreat

HeatherRating, 5 stars3 weeks ago

Shahabs place was Great! The location was perfect! There was 6 of us and could have easily roomed 10-12. The kitchen is fully equipped! I cooked almost every dinner but cooked every breakfast. The hot tub was great for peaceful evenings while playing cornhole and warming up by the fire pit. I would definitely stay there again while visiting Colorado Springs again!

The interior space features high vaulted ceilings with wooden beams, creating an open and airy atmosphere. A leather couch and comfortable chairs are positioned around a coffee table, while a dining area with a long table is nearby. Natural light streams through large windows, highlighting rustic decor.

5 out of 5 average rating, 7 reviews

Cozy 3BR A-Frame | Sauna + Deck & Mountain Views

MaggieRating, 5 stars3 weeks ago

I booked this with my pup for a last minute getaway from Denver and Connor and Dana were great! Fast communication, allowed me to check in early. The place was very cozy and the yard was big for my dog to get her zoomies out! The deck was very peaceful, loved using the traeger, and the home is in a more secluded area which was nice. The downstairs bed and couch were SO comfortable.

A view from a window reveals a scenic landscape featuring a garden area, rocky outcrops, and trees. Mountains are visible in the background under a clear blue sky. Outdoor seating is present on the patio, offering a peaceful atmosphere.

5 out of 5 average rating, 62 reviews

Mountain Glen Vista! License # 331228

LeAnneRating, 5 stars5 days ago

Outstanding view and comfort all in one. This house feels like staying at a relative's home in all the best ways - great kitchen, baths, linens, etc. and the outdoor grill was a nice touch. We felt right at home. It was a bit cold/wet to sit on the patio, yet we were able to thoroughly enjoyed the awesome view of Pikes Peak from the table and front windows at breakfast and in the evening. Deer even passed through the front yard several times. The neighborhood is very quiet and peaceful, but also super close to stores and restaurants in Woodland Park. Also very convenient for visiting Colorado Springs, Garden of the Gods, Manitou Springs, and Cripple Creek, as well as tons of hiking trails in surrounding areas. We loved it!

The rustic cabin exterior features a wooden porch supported by thick logs, inviting relaxation in nature. Surrounding pine trees provide a natural backdrop, while a bush with green foliage adds to the serene atmosphere. Large windows allow for natural light to brighten the space.

4.94 out of 5 average rating, 95 reviews

Prospector's cabin in Nat'l Forest

PatrickRating, 5 stars10 months ago

If you want to get away from it all, this is your place!!!! so peaceful and natural. no wifi. no cell phone. just like camping but with a nice bed, shower, and kitchen!!! host is SUPer responsive

4.99 out of 5 average rating, 279 reviews

A coffee maker is positioned on a wooden countertop, featuring a glass carafe and digital controls. A decorative leaf pattern on the wall complements the appliance's sleek black design, enhancing the cottage's modern functionality.

Cottage in Woodland Park

Mountain Paradise Cottage

MeganRating, 5 stars1 week ago

The cottage was absolutely perfect. As a solo traveler, it had everything I needed. The location was near to many things such as Pikes Peak, Manitou Springs and Garden of the Gods. The surrounding neighborhood was quiet and peaceful. I would definitely stay again.

The image captures a serene outdoor view at sunset, featuring deer grazing in a natural landscape surrounded by tall trees and vibrant fall foliage. A vintage swing sits nearby, adding to the peaceful ambiance of the setting against the backdrop of distant mountains.

4.98 out of 5 average rating, 50 reviews

Cozy cabin in Pike National Forest

ShambreeRating, 5 stars3 days ago

What a relaxing stay! Bryce's cabin was in the perfect location for privacy and seclusion, yet so close to tourist attractions in Manitou and Colorado Springs. We stayed for a week away with our two dogs and all four of us had the best time. The cabin was the perfect size, spotless, and comfortable! I cannot think of anything that would have improved our stay - we look forward to returning again!

4.98 out of 5 average rating, 64 reviews

Cozy Mountain Retreat on 3 acres

LisaRating, 5 stars1 week ago

Everything was just as described. Our kids loved exploring the property even though it rained every night. The space was perfect for our family. There were lots of games to play and toys and books for the kids in the loft. Everything was really clean and the beds were very comfortable. The location was close to everything that we wanted to do. We really enjoyed our time there and would book it if we ever come that way again.

A hot tub is depicted in the foreground, with clear blue water reflecting the surrounding nature. A scenic view of lush pine trees and a distant mountain is visible beyond, under a bright blue sky with a few soft clouds.