Pet-friendly holiday rentals in Woodland Park

4.99 out of 5 average rating, 136 reviews

A hot tub is positioned on a deck, offering views of lush green trees and distant mountains under a partly cloudy sky. The bubbling water invites relaxation while the natural surroundings create a serene atmosphere.

Cabin in Woodland Park

HOT TUB ~ 31 Acres ~Bring ATVs/Border Nat'l Forest

Looking for a quiet and secluded mountain getaway? This charming cabin on 31 acres that borders Pike National Forest is the perfect place to escape the hustle and bustle of everyday life. Enjoy breathtaking views of the surrounding mountains from the cabin's spacious deck, & keep an eye out for wildlife. The mountain getaway vibe is complete with a new hot tub, wood-burning stove & amazing views. You’re just a short drive from several mountain towns and 2 hours from Denver International Airport.

4.93 out of 5 average rating, 620 reviews

Tiny home in Florissant

Enjoy a Rocky Mountain winter escape

Escape to our cozy 1900s Bunkhouse! Rocky grandeur meets Colorado splendor. Western charm, stunning views of Pikes Peak & Continental Divide. Dogs (2) & horses welcome! Convenient corral nextdoor. Explore National Monument & Forest, miles of hiking trails, world-class fly fishing. Insider tips on local gems, restaurants & shops. 45 mins to Colorado Springs. Unwind under starry skies, enjoy landmark rock formations. Perfect for outdoor adventures with your furry friends! Make memories! Pets-fee

4.92 out of 5 average rating, 180 reviews

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

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 house in Woodland Park

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.

4.94 out of 5 average rating, 176 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.

4.98 out of 5 average rating, 173 reviews

The cabin's exterior highlights warm wooden siding and large windows, providing panoramic views of the surrounding landscape. A patio area with seating is visible, surrounded by trees and natural terrain. The hot tub is positioned nearby, enhancing the appeal of the outdoor space.

Cabin in Divide

Elk Spring Cabin, Divide home with a View

Secluded mountain cabin on 35 pristine acres with a wonderful view of Pike's Peak as a backdrop. Spring fed pond on the property and plenty of space for hiking, exploring, wildlife viewing as well as sledding and snowshoeing in the winter. Sleds, snowshoes are not provided. Elk Spring cabin has lodge decor with many handcrafted furniture pieces. Large windows in the living room to take in the view of trees and Pike's Peak. It offers seclusion yet minutes from grocery stores and restaurants.

Tiny home in Woodland Park

The exterior of a tiny house features a combination of green and wood paneling. Large windows allow ample natural light, while a welcoming door with steps leads inside. Gravel surrounds the house, enhancing the natural setting among surrounding trees.

4.93 out of 5 average rating, 576 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 narrow 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 🤗

4.88 out of 5 average rating, 415 reviews

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

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, 395 reviews

The A-frame cabin is illuminated by warm string lights, showcasing its inviting façade against a backdrop of a colorful sunset. A private hot tub is positioned beside the cabin on a stone patio, surrounded by greenery and natural setting.

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).

4.97 out of 5 average rating, 222 reviews

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

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.

Tiny home in Woodland Park

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.

4.96 out of 5 average rating, 199 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!

Cabin in Cascade-Chipita Park

A warm living area features large windows framing scenic views of surrounding trees. The space includes a leather sofa, a loveseat, and an accent chair arranged around a coffee table, complemented by a patterned area rug and a lamp that adds soft lighting.

4.92 out of 5 average rating, 128 reviews

The HeartRock House in Cascade

Welcome to the Heart Rock House in the beautiful mountains of Cascade, Colorado! ✓ 8 mins to the famous Pikes Peak Highway and Manitou Springs ✓ Expertly cleaned home ✓ I love 5 minutes away and am super responsive to texts and messages ✓ Ultra-fast, reliable internet ✓ Perfect for a family retreat in the mountains ✓ Game room with foosball and air hockey tables ✓ Deck for enjoying Colorado's sunny weather+mountain views+grilling up meals

4.91 out of 5 average rating, 209 reviews

The living room features a leather sofa and a recliner, complemented by a coffee table resting on a light area rug. A wooden console table with decorative items is present, while large windows allow natural light to brighten the space. The open kitchen and dining area are visible in the background.

Cabin in Divide

The Aspen Ridge Cabin

Welcome to The Aspen Ridge Cabin! This beautiful cabin located in the Colorado mountains gives you an authentic mountain retreat near local cities. Lovely views of the woods and mountains. Located 30 minutes from historic Manitou Springs and Cripple Creek, only 15 minutes away from beautiful Woodland Park, this cabin provides a cozy romantic getaway or a fun family adventure! 2 bedrooms, 5 beds. We hope you enjoy your stay!

Popular amenities for Woodland Park pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

Superhost

The living area features an open layout with plush seating arranged around a stylish electric fireplace. A smart TV is mounted on the wall, and large windows provide natural light. The dining area is visible in the background, accommodating a family dining table.

Home in Green Mountain Falls

4.79 out of 5 average rating, 142 reviews

Grandview 3BR Mountain Cabin w/ Hot Tub & EV

Superhost

The fenced backyard features a fire pit surrounded by four comfortable chairs. Soft string lights hang overhead, illuminating the gravel area that includes a green patch of grass and two hammock chairs for relaxation.

4.88 out of 5 average rating, 140 reviews

Dog ❤️, Gorgeous Yard, 14 min to Garden of the Gods

4.99 out of 5 average rating, 217 reviews

The Little House at RRCOS -Escape- Amazing views!

Home in Old Colorado City

A modern living space features a stylish gray sofa adorned with patterned cushions. A circular, wire base coffee table sits atop a textured area rug, complementing the wood flooring. Light from the window highlights a scenic artwork on the wall and the open kitchen area beyond.

4.93 out of 5 average rating, 327 reviews

Cozy Colo Cottage with love in Old Colorado City

A bright bedroom features a spacious bed adorned with an orange quilt and various decorative pillows. Soft lighting comes from pendant fixtures, adding warmth. A window, partly covered by light curtains, allows natural light to fill the room, while a small bedside table complements the decor.

4.94 out of 5 average rating, 358 reviews

Wildflower Cottage | Fenced Yard | 1 mile D-Town

Home in Green Mountain Falls

An outdoor deck area is furnished with comfortable seating and a glass-top table. The surrounding lush landscape features a spacious fenced-in yard and tall trees, offering a serene setting for relaxation and enjoyment.

4.92 out of 5 average rating, 250 reviews

Beautiful mountain getaway with hot tub!

4.94 out of 5 average rating, 234 reviews

A lit hot tub is nestled on a spacious deck, surrounded by trees. Soft blue lights illuminate the water, and string lights hang overhead, creating a serene evening atmosphere. Furnished lounge areas are visible in the background, inviting relaxation.

Home in Divide

Hot tub, mtn views, massage chair, & steam shower!

Home in Old Colorado City

The exterior of the house displays a contemporary industrial design, featuring a distinctive fenced yard made of various metal panels. A front door is visible, framed by a large window, and a pathway leads to the entrance. Trees and a mountainous backdrop enhance the setting.

4.99 out of 5 average rating, 121 reviews

THE WEST SIDE BEL AIR

Pet-friendly home rentals with a pool

5 out of 5 average rating, 33 reviews

A serene outdoor patio area features a table complemented by comfortable chairs, surrounded by lush greenery. A small waterfall pond is visible in the background, framed by tall trees and a clear sky, offering a peaceful natural setting.

Home in Larkspur

Forest Retreat, 2 floors, 3 bedrooms w/Hot Tub Spa

A lively sand volleyball court is captured, with participants in colorful jerseys actively engaged in the game. Spectators can be seen sitting on the sidelines among trees, while the sandy surface adds to the vibrant, energetic atmosphere of the outdoor activity.

Ranch in Florissant

4.86 out of 5 average rating, 80 reviews

cabin*pets, indoor pool, lake, hot tub, hiking

Townhouse in Colorado Springs

The Stark House | End-Unit Townhome | Pet Friendly

4.92 out of 5 average rating, 250 reviews

A bright living area is furnished with a green sofa and a white slipcovered couch. A wooden coffee table sits in front. A dining table is positioned near a window, allowing natural light to illuminate the space. Decorative plates and a world map adorn the wall.

Flat in Colorado Springs

Quite Spacious Apt w/ Game Table, Bball Court

A spacious living area features a comfortable dark sofa and two patterned armchairs surrounding a glass coffee table. Natural light fills the room through large windows, highlighting the open concept layout that connects to the dining area and kitchen in the background.

Townhouse in Colorado Springs

4.86 out of 5 average rating, 184 reviews

Resort-Style Townhome | Pool, Hot Tub & Gym Access

The exterior of the home features a light-colored stucco façade and a welcoming entrance. A vibrant flowering shrub adds a pop of color, while landscaped stone and gravel complement the yard. Two garage doors and a concrete driveway provide convenient access.

4.67 out of 5 average rating, 9 reviews

The Mile High Oasis

Cabin in Garden of the Gods

5 out of 5 average rating, 4 reviews

Timber Lodge #8

Cabin in Green Mountain Falls

A spacious living area features wooden beams and a cozy leather couch, complemented by a round coffee table. Large windows allow natural light to brighten the space, revealing a fully equipped kitchen and dining area with seating for six in the background.

5 out of 5 average rating, 46 reviews

Cabin Fever? This One’s the Good Kind

Private, pet-friendly home rentals

4.96 out of 5 average rating, 291 reviews

The exterior of a charming A-frame cabin features a sloped roof and a welcoming blue facade. A small porch is adorned with potted plants, while a pathway of stone slabs leads through landscaped greenery. Sunlight filters through surrounding trees, enhancing the inviting atmosphere.

Cabin in Palmer Lake

𓃲A-Frame on Palmer Lake𓃲 Firepit┃Foosball┃Grill

Guest house in Palmer Lake

A rustic wooden cabin is nestled among snow-covered trees, presenting a serene winter scene. The building features a sloped roof and a single satellite dish, surrounded by a blanket of snow on the ground. The town of Palmer Lake is visible in the background.

4.95 out of 5 average rating, 257 reviews

Quaint and Historic Studio Cabin

Cabin in Cascade-Chipita Park

The cozy cabin exterior is surrounded by tall evergreen trees, featuring a red facade and large windows. A green lawn filled with wild grass leads up to the entrance, while a small patio area is visible beside the house.

4.97 out of 5 average rating, 145 reviews

Chipita Park Creekside Retreat

Flat in Old Colorado City

A covered porch offers expansive views of the surrounding mountains and greenery. Two lounge chairs are positioned on a vibrant blue patterned rug, creating a serene outdoor space to relax and enjoy the scenery.

4.94 out of 5 average rating, 781 reviews

Downtown Old Colorado City with Panoramic Views

Cabin in Cascade-Chipita Park

A log cabin exterior is surrounded by mature evergreen trees, with a fenced area to the side. A stone pathway leads to a welcoming front porch, and the landscaping features green shrubs and plants along the walkway.

4.82 out of 5 average rating, 335 reviews

Creekside Cabin Near Pikes Peak

4.93 out of 5 average rating, 213 reviews

A scenic view reveals rolling hills adorned with evergreen trees. Snow-dusted peaks stretch across the horizon, complemented by a diverse landscape featuring both dense forests and open spaces. The atmosphere reflects tranquility, with soft light casting a gentle glow over the vast wilderness.

Cabin

Red Door Cabin

Cabin in Green Mountain Falls

A rustic cabin sits amidst tall trees, with a staircase leading to its entrance. The structure features a mix of dark wood and stone, framed by the natural beauty of the surrounding forest. A vibrant sunset casts a warm glow in the evening sky.

4.98 out of 5 average rating, 291 reviews

Mountain Cabin: Hot Tub, Fireplaces, Loft, Views