Holiday rentals in Woodland Park

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Top-rated holiday rentals in Woodland Park

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The chalet's A-frame structure is framed by tall pine trees, showcasing large windows that invite natural light. A gentle plume of smoke is rising from the chimney, indicating a warm interior. The outdoor deck offers a seating area for relaxation amidst a scenic mountain setting.
Cabin in Woodland Park
4.98 out of 5 average rating, 106 reviews

Fireplace, Dogs YES, Hot Tub, 2 Decks, Scenic Vws

Escape to the “Blue Spruce Chalet”. A redesigned, 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 fast Wi-Fi, a fully equipped kitchen, a wood-burning stove, an outdoor firepit, & 2 decks with stunning mountain & sunset views. Star gaze from the hot tub. You may never want to leave this slice of heaven. Perfect for a quick getaway.

Guest favourite
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, 118 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.

Top guest favourite
A charming cabin is nestled among tall pine trees, with a snow-covered landscape surrounding it. The house features a front porch with wooden railings, and natural stone accents are visible on the exterior. A clear blue sky is contrasted by fluffy clouds above.
Cabin in Cascade-Chipita Park
4.99 out of 5 average rating, 173 reviews

Classic Throwback Colorado Mountain Cabin

Take it easy at this unique and tranquil getaway. A family cabin crafted in the 1940s, unchanged with the exception of tastefully done upgrades and improvements. Authentic western decor and knotty pine interior. Easy access to nearby hiking and attractions. Minutes from the beautiful small mountain towns of Green Mountain Falls, Manitou Springs and Woodland Park. Local attractions including Pikes Peak, North Pole Santa’s Workshop, Cripple Creek, Garden of the Gods are just minutes away.

Top guest favourite
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.
Cabin in Woodland Park
4.88 out of 5 average rating, 415 reviews

Cabin with Pikes Peak View in WP License#329434

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

Top guest favourite
The unique octagon structure of the Treehouse is surrounded by lush greenery, with tall trees and fog creating a serene atmosphere. The design elevates the home above the forest floor, showcasing wooden supports and inviting outdoor stairs leading up to the entrance.
Treehouse in Cascade-Chipita Park
4.99 out of 5 average rating, 294 reviews

Luxury Treehouse Escape | Near Pikes Peak+Views

Welcome to the Treehouse - Your Colorado Getaway. Perched high in the trees with panoramic views, a HUGE bathtub, coffee bar with local coffee, two decks, and KING sized bed, you’ll never want to leave. This completely remodeled, octagon treehouse is just 15 minutes from most attractions in Colorado Springs and 5 minutes from the famous Pikes Peak Highway and gorgeous hiking trails - you are right in the middle of plenty to do while also being tucked away in your own little forest paradise.

Top guest favourite
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.
Cabin in Woodland Park
4.97 out of 5 average rating, 222 reviews

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

Stunning remodeled 1930's cabin with one of the best views of Pikes Peak in town! The Sugar Shack has a hot tub with views, dog friendly with a fenced-in backyard, and foosball table for fun times. It offers unique charm and is nestled in the heart of downtown and located one block from beautiful Memorial Park and Main street. Walk to restaurants, a brewery and shopping. Watch TV on a LED smart TV's. Or catch live sporting events on Dish Satellite. Stocked kitchen for home cooked meals.

Guest favourite
A firepit table is featured in the foreground, with a steaming mug resting on its surface. In the background, a scenic view of snow-covered mountains and a wooden fence can be seen under a partly cloudy sky.
Home in Woodland Park
4.91 out of 5 average rating, 125 reviews

Pikes Peak BrightStar Boutique!

Kick back and relax in this calm, stylish Boutique Tiny Home. Pikes Peak Brightstar Boutique is a unique one-of-a-kind Tiny Home with many creature comforts such as AC/Dual Heating system, internet connected TV, Washer/Dryer, vibrant lighting and a gorgeous loft with magnificent views of Pike Peak from the moment you wake up. The unit also features a spacious Tiny Home bathroom, stocked K-Cup Coffee maker and full kitchen to cook home cooked meals. Extremely cozy, quiet and entertaining!

Guest favourite
The A-frame tiny home is surrounded by a serene winter landscape, with snow-covered trees and a dusting of snow on the porch railing. A few deer are seen near the entrance, adding to the tranquil atmosphere of the setting.
Tiny home in Woodland Park
4.96 out of 5 average rating, 175 reviews

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

Guest favourite
Home in Woodland Park
4.9 out of 5 average rating, 347 reviews

Tiny House 🌟 Pike’s Peak Views 🌟

Imagine waking up to the symphony of chirping birds and the scent of pine wafting through your window, all while knowing that a short stroll will lead you to conveniences like cafes, shops, and local markets. You can indulge in invigorating hikes during the day and return to unwind with a hot shower, a cozy bed, and wi-fi. Your mountain getaway doesn't have to mean sacrificing convenience-come experience the best of both worlds at our charming tiny house!

Guest favourite
A modern kitchen space features a sleek white countertop with seating for six, beside a warm fireplace integrated into a black feature wall. A cozy brown armchair is positioned nearby, and ample natural light filters through the window, creating an inviting ambiance.
Cabin in Divide
4.97 out of 5 average rating, 121 reviews

Romantic Lakefront Cabin - Hot Tub-VIEWS!

Whether you’re a couple seeking a romantic escape or a small group looking for a relaxing retreat, our lakefront cabin offers the perfect blend of cozy charm and stunning mountain views. Unwind with serene lake vistas from the deck and take in breathtaking sunsets that light up the sky each evening—creating unforgettable moments together. Located just 45 minutes from Colorado Springs, the cabin is also near exciting attractions. Book NOW!

Top guest favourite
A modern mountain home is surrounded by tall coniferous trees, showcasing large windows that reflect natural light. A spacious deck extends from one side, offering views of the serene landscape. The structure is positioned on elevated terrain, enhancing its connection with the outdoors.
Home in Divide
4.98 out of 5 average rating, 239 reviews

Mountain Sun cabin, amazing views and hottub!

Gorgeous secluded mountain home on 35 acres. Mountain Sun cabin has it all! An amazing view of Pikes Peak and the surrounding area, hottub, many upgrades throughtout the home including log furniture and a mountain theme. The Pikes Peak area has so much to offer: visiting Pikes Peak, Cripple Creek, the Royal Gorge, Garden of the Gods, white water rafting as well as an abundance of outdoor activities summer or winter.

Top guest favourite
An aerial view showcases a charming cabin nestled in a green landscape, surrounded by trees and hills. A patio area with seating is visible, along with a gravel driveway leading up to the entrance.
Cabin in Green Mountain Falls
4.94 out of 5 average rating, 137 reviews

Namaste at Hondo

This gorgeous, cozy cabin is the perfect place to unwind, located within walking distance of several hiking trails, the Green Mountain Falls lake, restaurants and local shops. Relax on the huge comfortable couch or enjoy the outdoor space. This recently remodeled casita has major southwest vibes.

Popular amenities for Woodland Park holiday rentals

When is the best time to visit Woodland Park?

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Woodland Park?

    Yes! Work meets play with ease at over 110 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 $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Woodland Park have wifi?

    Absolutely! We offer over 60 house rentals with wifi in Woodland Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodland Park have self check-in?

    Absolutely! We offer over 70 house rentals with self check-in in Woodland Park. Enjoy a tailored experience with all the comforts you desire.

  • Do cabin rentals in Woodland Park have a bbq area?

    Absolutely! We offer over 30 cabin rentals with a bbq area in Woodland Park. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Woodland Park?

    Woodland Park has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Cabin Rentals in Woodland Park?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 30 homes with self check-in, over 30 homes with a bbq area, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Woodland Park

  • Total holiday rentals

    Explore 190 holiday rentals in Woodland Park

  • Nightly prices starting at

    Woodland Park holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 17,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wifi availability

    190 of Woodland Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Woodland Park rentals

  • 4.9 Average rating

    Woodland Park stays are highly rated by guests – averaging 4.9 out of 5!

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