Holiday rentals in Woodland Park

4.93 out of 5 average rating, 160 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!

4.98 out of 5 average rating, 249 reviews

Cabin in Divide

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

Welcome to your historic mountain retreat at Eagle Ridge! The cabin is a stunning 360 sq ft handcrafted woodwork home situated on a gated 43-acre property with access to private walking trails and panoramic views of Pikes Peak that will take your breath away. The peaceful and quiet atmosphere of the cabin instantly enables one to forget about the busyness of life and rest and/or focus on a birthday, anniversary, or personal retreat. The hot tub is filled with fresh water for every guest.

4.88 out of 5 average rating, 384 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

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

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.

4.98 out of 5 average rating, 317 reviews

Magical A-Frame w/in Nat'l Forest-Firepit+MtnViews

►Escape to a secluded a-frame amidst 1+ million acres of pristine national forest ►Hike a 1.5 mile private trail just out your back door ►Unwind by the crackling fire pit under a star-filled sky ►Designed by boutique NYC interior design firm ►Complimentary organic local coffee, beer, and healthy snacks ►Prepare gourmet meals in the chef's kitchen ►Stocked with: board games, puzzles, books, yoga mats, and more ►Cozy up next to the inviting wood-burning stove ►High-end mattress and bedding

4.99 out of 5 average rating, 111 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

4.93 out of 5 average rating, 523 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, 332 reviews

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

Cabin in Cascade-Chipita Park

4.99 out of 5 average rating, 184 reviews

Riverhouse North~Luxury~Creekside~Cabin

RiverHouse, yes, there’s a river… in the backyard… right next to the private hot tub… around the corner from the massive gas fire pit. So unless you hate watching local wildlife, the sound of the creek, and a luxurious back patio that’s perfect for all seasons, then you should probably book here. Ok, here are the details: kitchen stocked with a curator's touch, heated towel rack, remote control gas fireplace, gas grill, 2023 top-to-bottom remodel. Get this property before it books!

4.96 out of 5 average rating, 169 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!

4.97 out of 5 average rating, 141 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

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Woodland Park holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Woodland Park

4.94 out of 5 average rating, 50 reviews

Come to the Hideout! Hot Tub, Fire Pits & Views!

BrittanyRating, 5 stars14 months ago

This cabin was amazing! Awesome location, private and beautiful. The fenced in backyard was greats for our dogs. Lots of fantastic hiking close by. Just a short drive to town which had lots of great restaurants. We had the best time and would definitely come back.

5 out of 5 average rating, 63 reviews

Home in Woodland Park

Mountain Glen Vista! License # 331228

LeAnneRating, 5 stars2 weeks 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!

4.99 out of 5 average rating, 280 reviews

Cottage in Woodland Park

Mountain Paradise Cottage

MeganRating, 5 stars2 weeks 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.

4.98 out of 5 average rating, 46 reviews

Cozy Cabin in the Woodland Park

DanielRating, 5 stars2 weeks ago

My wife and I spent a few days at Michelle’s place and couldn’t have had a better experience. The home was spotless, thoughtfully stocked, and very well cared for. The views were absolutely incredible - waking up to the forest right outside the window was unforgettable. If you’re into hiking, backpacking, or just enjoying the outdoors, the location is perfect. There’s also a charming town nearby with plenty to explore. It was honestly hard to leave - we’d absolutely stay again in the future! Thank you again, Michelle!

4.96 out of 5 average rating, 49 reviews

Flat in Woodland Park

Vintage Velvet Haven - newly added hot tub!

DeAnnRating, 5 stars1 week ago

The apartment was even cuter in person. absolutely perfect. Check in and out was super easy. The kitchen had everything that's needed. the bathroom had a beautiful deep tub with hot water. The bed was very comfortable. The area was very peaceful and plenty of places to get out into nature and hike or whatever is wanted. I would most definitely recommend!

4.98 out of 5 average rating, 49 reviews

Cabin in Florissant

New! A-Frame w/ Hot Tub + Stargazing Dome

TitusRating, 5 stars1 week ago

5 ⭐️⭐️⭐️⭐️⭐️ We absolutely loved our stay in this place!! It was so cozy, down to the little details all around. Everything was spotlessly clean. Brooke's instructions and information for the cabin were very helpful. She is a communicative and accommodating host (: From the stargazing dome to hot tub to the loft area upstairs - it made for the perfect getaway!! We hope to come back again!!

5 out of 5 average rating, 34 reviews

Home in Woodland Park

Mountain View-EV Charger-Walk to town—Licensed

JoshRating, 5 stars10 months ago

It was a great stay. We had so much fun and the house was perfect for our family of 7. John was super responsive and immediately answered questions before and during the stay. The only minor complaint is that Apple Maps took us to the driveway of the business just before it on the road, because it did not recognize their new driveway. We had to know where to turn in based on what the pictures looked like of the house.