Vacation rentals in Woodland Park

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Top-rated vacation rentals in Woodland Park

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

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Guest favorite
The interior space features wooden cabinetry and a compact kitchenette with essential appliances. A sofa is positioned nearby, and a dining table occupies one corner. Natural light floods in through multiple windows, enhancing the warm ambiance of the cabin.
Guesthouse in Woodland Park
4.94 out of 5 average rating, 179 reviews

Rose Mountain Escape Pet friendly W/pet fee

Rose Mountain escape has beautiful views. Located 5 miles from Charis,, 15 mins from downtown Woodland Park & 2hrs from Breckinridge, 2 blocks from BLM land allows ATVs, Motor/Mountain bikes and walks through the forest. Small cabin with a VERY STEEP STAIRCASE to the bedroom. We have a large deck with chairs, gas fire pit & hot tub, grill for your use. We have great WiFI. We have kitchenette, washer and dryer. Pet friendly w/ CLEANING FEE list pet on reservation! SMOKING OUTSIDE. 420 friendly.

Guest favorite
A white coffee cup sits on a saucer on a woven placemat, with lush green plants in a glass bowl nearby. Large windows reveal unobstructed views of the mountains in the background, allowing natural light to illuminate the space.
Tiny home in Woodland Park
4.91 out of 5 average rating, 280 reviews

Boutique TinyHome w/Direct View of PikesPeak!

If mountain views are what you want, you have found your get away with DIRECT unobstructed views of world famous Pike's Peak. This one of a kind cozy tinyhouse is nestled in a lovely Tiny home community called Peak View Park and is surrounded by breathtaking mountain views located in Woodland Park. Close to great restaurants and a variety of grocery stores. Woodland Park is located just 20 minutes west of Colorado springs on Highway 24. Come and experience the ā€œCity above the Cloudsā€.

Top guest favorite
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
4.97 out of 5 average rating, 226 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
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, 273 reviews

Private Suite w/Trees & Awesome Peak View 328878.

Picture-perfect Pikes Peak views from your living room, bedroom, and 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 Pines, Aspen, and beautiful hiking trails right up the street, you may never want to leave.

Top guest favorite
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, 420 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

Guest favorite
The cozy living area features a comfortable brown sofa positioned near a large screen TV. Natural light enters through the two windows, complemented by ceiling fan lighting above. A ladder leads to the loft area visible above, while a small dining set is situated in the corner.
Tiny home in Woodland Park
4.94 out of 5 average rating, 268 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!

Top guest favorite
A rustic log cabin is set against a backdrop of lush greenery, featuring a wrap-around deck adorned with vibrant flower pots. Sturdy wooden stairs lead to the entry, surrounded by natural stone accents and shaded by tall pine trees.
Cabin in Cascade-Chipita Park
4.97 out of 5 average rating, 161 reviews

Rustic Historic Colorado Mountain Cabin Pikes Peak

This historic rustic log cabin built in 1953 has been updated. It sits near the foot of Pikes Peak and Pike National Forest & 17 minutes from Downtown Colo Spgs. The cabin sits at 7800' and is usually cool and comfortable temperature inside, we have added Central Air Conditioning to further enhance your comfort. Denver Airport (DIA) is a 90 minute drive Colorado Springs Airport (COS) is a 32 minute drive. Hiking, Fishing, Kayaking, Garden of the Gods, North Pole Santas Workshop, USAFA,

Guest favorite
A cozy cabin is nestled among tall pine trees, surrounded by a snow-dusted landscape. Sunlight filters through the branches, illuminating the faƧade of the cabin with a warm glow. The large sitting porch is visible, integrating the structure with its natural surroundings.
Cabin in Florissant
4.94 out of 5 average rating, 144 reviews

Cozy Vintage Cabin in Florissant Colorado

Tucked away in the peaceful mountain landscape yet just minutes from the charming town of Florissant, this 500 sq ft, 1-bedroom, 1-bath cabin is the perfect balance of style, comfort, and convenience. Inside, you’ll find a thoughtfully designed interior that blends vintage furniture with eclectic, one-of-a-kind touches. The well-equipped kitchen includes an apartment size oven, fridge and microwave. • An easy day trip to historic mountain towns, scenic byways, and outdoor adventure spots

Guest favorite
The exterior of the chalet is illuminated by warm string lights at dusk, showcasing a wood and glass structure surrounded by trees. A soothing hot tub is visible on the deck, offering a perfect spot for relaxation under the evening sky.
Cabin in Woodland Park
4.98 out of 5 average rating, 110 reviews

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

Escape to the ā€œBlue Spruce Chaletā€. 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.

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.
Cabin in Woodland Park
4.86 out of 5 average rating, 138 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.

Top guest favorite
A cozy bedroom features a queen bed framed with rustic wooden posts and adorned with a patterned quilt. A round mirror and a nightstand complement the room, with natural light illuminating the space through a nearby window.
Cabin in Florissant
4.96 out of 5 average rating, 112 reviews

Cheerful 1-bedroom cabin with hot tub

Take it easy at this unique and tranquil getaway. Cozy 1-bedroom/ 1 bath cabin with a hot tub. The fenced-in yard with a large outdoor patio is perfect for entertaining and cooking out. Come enjoy the endless wildlife and ample amount of outdoor activities. Located in Florissant. We are 1 hour from Colorado Springs and less than 30 mins from Woodland Park. 4 Wheel drive is recommended for the winter months.

Top guest favorite
A winding gravel driveway leads to a charming guest house surrounded by tall trees and lush greenery. Flanking the entrance, a red telephone booth and a small stone structure add unique character to the property. Mountain peaks are visible in the background.
Guest suite in Palmer Lake
4.97 out of 5 average rating, 229 reviews

Digbycrofts Guest House

Cozy guest house on the south side of ā€˜ Digbycrofts Manor ā€˜ in beautiful Palmer Lake, at the base of National Forest trail . Just under a mile from Pinecrest Weddings and Event Center, 3 minutes from the lake and restaurants and 20 minutes from the Air Force Academy. Ideal for mountain biking, hiking and lake activities. SUNDANCE WAGON close by for 2 more guests, also available through Airbnb.

Popular amenities for Woodland Park vacation 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 house rentals in Woodland Park?

    Experience the best of Woodland Park with our house rentals, starting at about $10 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 self check-in?

    Absolutely! We offer over 60 house 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 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 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 cabin rentals in Woodland Park?

    Woodland Park has more than 30 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a bbq area, over 60 homes with wifi, over 60 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Woodland Park

  • Total vacation rentals

    Explore 190 vacation rentals in Woodland Park

  • Nightly prices starting at

    Woodland Park vacation rentals start at ļŗ©.ļŗ‡37 per night before taxes and fees

  • Verified guest reviews

    Over 17,050 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    190 of Woodland Park vacation rentals include wi-fi 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!

Destinations to explore

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