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
Home in Woodland Park
4.9 out of 5 average rating, 340 reviews

Tiny Home Getaway | Pikes Peak Views + Walkable

Retreat to your Woodland Park tiny home! With mountain views from the porch, this tiny house is tucked among the trees in a quiet tiny home community. Located just off the main road and about ½ mile from coffee, groceries, and local dining, it offers both convenience and a peaceful feel. Spend your days exploring nearby hiking, Rampart Reservoir, and Cripple Creek, then settle in with fast WiFi, a full kitchen, Roku TV, and easy self check-in. A 4.9★ Guest Favorite. 4WD/AWD recommended Sept–May.

Guest favorite
The living area showcases a pair of comfortable gray sofas arranged around a coffee table. A large television displays a virtual fireplace, creating a cozy ambiance. A light fixture casts a warm glow, and a dining area with a wooden table provides additional seating.
Home in Woodland Park
4.92 out of 5 average rating, 183 reviews

Little Woody's Hideaway-(4)DownTown - 329662

License 329662. 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 for all your adventures!

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 “City above the Clouds”.

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.

Guest favorite
A spacious cabin bedroom showcases a king-sized bed adorned with textured linens and decorative pillows. Warm wood tones and rustic decor create a cozy environment. An orange door invites light and views from outside, while a sliding barn door leads to the bathroom area.
Cabin in Lake George
4.9 out of 5 average rating, 138 reviews

Luxury King Bed | Mountain, Lake & Dark Sky Views!

ᨒ༄ King Bed Cabin: Lake + Mtn Views, perfect for a couples retreat! ♥Enjoy the community patio, outdoor stone fireplace, barrel wood sauna, grills, + outdoor dining ♥Unwind in the stone tile bathroom, heated & lighted toilet seat, spacious standup shower ♥Enjoy a fully stocked kitchenette w/ g00gle hub smart display ♥43-inch LG Smart TV: cable, streaming apps like hulu + netflix ♥Indulge in romantic activities such as the spa, hot air balloon rides, casino fun, or a delightful wine tasting!

Top guest favorite
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 favorite
The exterior of a charming A-frame cabin is showcased, featuring a wooden deck with a railing. Large floor-to-ceiling windows allow ample natural light into the space, providing a view of the surrounding trees and outdoor seating area.
Cabin in Florissant
4.92 out of 5 average rating, 651 reviews

☀Cabin with Mtn Views☀ A-Frame Nature Getaway

★Location: Minutes to CO Wolf + Wildlife Ctr, award-winning Paradox Beer Company, Fossil Beds, Lake George, Mueller State Park. Short Drive to Pikes Peak, Garden of the Gods ★OUTDOORS: Nearby hiking, biking, snowshoeing, horseback riding, cross country skiing, rock climbing, white water rafting ★DINING/SHOPS: Short drive to Woodland Park & Historic Manitou ★VIEWS of the Continental Divide from the large back porch & bedroom balcony ★Grill + Firepit ★Brand new comfy beds ★Equipped Kitchen

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, 156 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

Guest favorite
The living area features a comfortable gray sofa paired with a distinctive black wingback chair. A decorative coffee table is centered on a soft area rug, while elegant light fixtures hang above. Natural light pours in through clerestory windows, enhancing the airy ambiance.
Tiny home in Woodland Park
4.96 out of 5 average rating, 204 reviews

Charming Mountain Retreat with private HOT TUB

Welcome to Mini Maison, the coziest tiny home in Woodland Park! Whether you're looking to unwind and refresh or explore the natural beauty the area has to offer, our beautifully decorated home was curated with comfort and luxury in mind. We're located just 10 minutes from Pikes Peak, the most visited mountain in the USA. Garden of the Gods, Manitou Springs and Cave of the Winds are also nearby. Come enjoy the Colorado mountains, our private and peaceful retreat is waiting for you!

Top guest favorite
Cabin in Divide
4.98 out of 5 average rating, 322 reviews

Cabin Getaway: Hot Tub, Sauna & Mtn View, 43 acres

Romantic Mountain Retreat at Eagle Ridge Escape to your private mountain retreat at Eagle Ridge, where rustic charm meets modern comfort. This stunning handcrafted 360 sq ft cabin, nestled on a gated 43-acre estate, offers breathtaking panoramic views of Pikes Peak and access to forest and meadow trails. It is the perfect place to celebrate birthdays, anniversaries, honeymoons, or simply enjoy a personal retreat surrounded by the beauty of Colorado.

Guest favorite
Cabin in Woodland Park
4.91 out of 5 average rating, 174 reviews

Beautiful Cabin w/ Decks/Views/sauna/hot tub!

Your dream mountain escape—cozy, newly remodeled, and view-filled. 🌄 Panoramic mountain views ♨️ Hot tub + fire pit on huge deck 🔥 Cozy, stylish interior 🏓 Basement ping pong + sauna 🛏️ Sleeps 6 comfortably (up to 8 w/ approval) 🐾 Wildlife sightings in a peaceful setting A perfect blend of comfort and adventure.

Top guest favorite
The exterior of the cottage showcases a charming yellow façade with green shutters and a welcoming front door. Two black chairs are positioned outside, providing a cozy seating area under the shade of nearby trees.
Cottage in Woodland Park
4.99 out of 5 average rating, 304 reviews

Mountain Paradise Cottage

Enjoy your stay in the Mountain Paradise Cottage featuring a relaxing cottage-style decor that you will find relaxing, cozy and all together fun! The cottage was originally the caretaker's cottage for the Maytag house. Conveniently located in the center of town and only 2 miles from Charis!

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 ﺩ.ﺇ37 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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  3. Colorado
  4. Teller County
  5. Woodland Park