Pet-friendly holiday rentals in Woodland Park

4.98 out of 5 average rating, 162 reviews

The image collage features four areas of the Tecumseh Lodge. A living room showcases a leather sectional, a stone gas fireplace, and large windows displaying snowy trees outside. The loft bedroom displays a queen bed with a cozy couch, while the downstairs master bedroom features a king-size bed and beautifully arranged bedding.

Chalet in Woodland Park

Cozy Forest Escape w/ Hot Tub & Scenic Views

Indulge in the ultimate retreat experience at the enchanting Tecumseh Lodge, nestled near Pike's Peak, a mere 15-min drive from downtown Woodland Park. Escape to a haven designed for serenity seekers, nature lovers and remote workers alike. Wake up to a golden sunrise on our spacious deck with cozy furniture and a warming space heater. In the evening, unwind in our hot tub, surrounded by all the stars & nature. Book your escape at Tecumseh Lodge for a luxurious blend of comfort and nature.

4.98 out of 5 average rating, 129 reviews

A panoramic view showcases snow-capped mountains rising majestically above a densely wooded landscape. Tall evergreens dominate the foreground, contrasting beautifully with the clear blue sky and distant peaks.

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.

The cabin is nestled among trees, with expansive windows reflecting warm sunlight at sunset. The architectural design features a prominent stone chimney, enhancing the rustic charm. Surrounding hills add to the serene atmosphere, creating a sense of tranquility in nature.

5 out of 5 average rating, 204 reviews

Be Inspired! Luxe Cabin Retreat w/Hot Tub & Views

Relish your time in this one of a kind Luxury Cabin affectionately called, Peaceful Pines Ridge. Nestled between Colo Spgs (45 min) & Breckenridge (60 min), this fabulous mountain retreat feels lost in the Pines but is tucked away only a mile off Hwy 24 near Lake George while nestled on 40 private acres boasting grassy meadows, rock formations, timbered canyons and ridges with a rippling stream to boot. Enjoy thousands of acres of National Forest on 3 sides w/full Modern Tech at your fingertips!

4.96 out of 5 average rating, 141 reviews

An inviting outdoor patio is illuminated by string lights, featuring a stone fireplace surrounded by comfortable seating. The scene includes several dark wooden chairs arranged around a fire pit, with trees adorned by lights creating a cozy ambiance against the night sky.

Cabin in Lake George

Dark Sky Stargazing from Firepit, Mountain Views

☾ ✩ Dark Sky Zone: All exterior lighting is "Dark Sky Friendly," allowing for stunning views of the Milky Way in this designated Dark Sky area ☾ ✩ ✧Community Patio: Outdoor Stone Fireplace, Propane Fire pits & String Lights ✧Barrel Sauna ✧Grill ✧Game Hub: Corn hole + more! ✧LG Smart TV: Cable & Streaming Apps ✧Fully Stocked Kitchenette ✧BR w/ a Heated Toilet Seat ✧Minutes to Florissant Fossil Beds, 11 Mile Reservoir, Colorado Wolf and Wildlife Center + Mueller State Park. Walk to 11 Mi Canyon.

4.94 out of 5 average rating, 110 reviews

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

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.

4.98 out of 5 average rating, 221 reviews

Into the Woods Aframe | Hot Tub | FirePit| 6 Acres

✨ Step into an ideal Colorado getaway at this renovated A-Frame. 🏔️ It is truly a gem with comfort and minimalism in mind. 🎨 Enjoy the modern mountain aesthetic and design! 🌲 The A-frame sits on 6 acres filled with pine and aspen trees and rock outcroppings, allowing for a secluded and private stay. 🛁 A space like this would not be complete without a hot tub to soak in under a star-filled sky. 🚗 Short drive to neighboring mountain towns: Divide, Florrisant, Lake George, and Cripple Creek.

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, 563 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 🤗

4.97 out of 5 average rating, 220 reviews

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

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.

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.

4.99 out of 5 average rating, 376 reviews

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).

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.

4.93 out of 5 average rating, 210 reviews

Red Door Cabin

While staying at Red Door Cabins you will enjoy breathtaking views, amazing rock formations, beautiful pine and aspen trees, a firepit, silence and stars. Have fun finding pieces of petrified wood, geodes, wild berries, and mushrooms on the property and surrounding area. You will get visited by deer, squirrels, maybe a family of foxes and occasionally local black bear or two. So, don’t forget your camera! THERE ARE TWO CABINS ON THE PROPERTY SO YOU MAY HAVE NEIGHBORS DURING YOUR STAY .

The A-frame cabin is nestled on a hillside, surrounded by tall pine trees. Sunlight filters through the clouds, illuminating the outdoor deck and providing a glimpse of the expansive natural landscape. The structure's triangular roof design stands out amidst the greenery.

5 out of 5 average rating, 177 reviews

Indigo A Frame | Dog Inclusive, Hot Tub, Secluded

★ King bed (Helix Mattress) + lots of cozy blankets ★ Dog inclusive ★ 4 private, wooded acres + mountain views ★ Hot tub ★ Wood stove with plenty of firewood and fire-starting supplies provided ★ 1 Hour to Colorado Springs, 2 Hours to DIA This charming vintage A Frame is nestled in the forest off a quiet road, offering mountain views and natural immersion. You will likely see more deer, birds, and chipmunks than other humans, but if you’d like to venture out, Divide is 18 minutes away!

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, 191 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!

Popular amenities for Woodland Park pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A well-appointed kitchen exhibits modern cabinetry in deep green, complemented by a marble backsplash. Stainless steel appliances, including a fridge and dishwasher, provide functionality. A dining table set for four is positioned nearby, enhancing the kitchen's inviting atmosphere with natural light streaming through the window.

4.97 out of 5 average rating, 191 reviews

Casita Noir | King Bed, Private Patio w/ Fire Pit

A private hot tub is positioned in a fenced yard, surrounded by green turf. Soft lighting from patio string lights and lanterns creates a serene evening atmosphere. Steam rises from the tub, indicating warmth and comfort.

4.99 out of 5 average rating, 183 reviews

Private Basement*HotTub*Washer+Dryer*Full Kitchen*

The exterior of a modern two-story guest house is shown, featuring large windows and a combination of light and dark materials. The structure is situated amidst tall pine trees on a gravel driveway, with a single carport located beneath the upper level.

4.99 out of 5 average rating, 181 reviews

Private Guest House in the Forest

4.98 out of 5 average rating, 116 reviews

A hot tub is positioned outdoors on a wooden deck, overlooking a serene forested area. Steam rises gently from the bubbling water, surrounded by snow-dusted trees and a clear blue sky. The space is designed for relaxation and enjoying nature.

Home in Florissant

HOT TUB!~Game Room~Family Fun~Pet's Free~Starlink

Home in Old Colorado City

A spacious outdoor deck is shaded by a large fabric canopy, featuring comfortable wicker seating and a grill. The surrounding area includes gravel landscaping with flower planters and a privacy fence, creating a cozy and inviting space for relaxation.

4.83 out of 5 average rating, 269 reviews

The Clubhouse

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, 315 reviews

Cozy Colo Cottage with love in Old Colorado City

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.

4.93 out of 5 average rating, 242 reviews

Beautiful mountain getaway with hot tub!

4.96 out of 5 average rating, 124 reviews

Couples Getaway | Hot Tub, Fire Pit, Grill | Dogs

Pet-friendly home rentals with a pool

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.

Farm in Florissant

4.86 out of 5 average rating, 80 reviews

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

Apartment in Colorado Springs

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.

4.91 out of 5 average rating, 230 reviews

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, 181 reviews

Stylish NEW Home Close to Downtown

Cabin in Garden of the Gods

An inviting cabin interior features warm wooden walls and a vibrant red accent wall. A cozy sleeping area is furnished with a spacious bed and bedside tables. A kitchenette with modern appliances, including a microwave and refrigerator, is positioned in the corner, enhancing the functionality of the space.

5 out of 5 average rating, 7 reviews

Timber Lodge #18

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 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, 44 reviews

Take a Hike, Kids! Literally. Fun Family Getaway

A private above-ground pool is featured in a fenced backyard surrounded by landscaped grass. The two-story home is visible in the background, with a wooden deck and patio furniture nearby. A swing set is also present, creating a family-friendly outdoor space.

4.96 out of 5 average rating, 28 reviews

King's Oasis

A spacious vacation home is set against a bright blue sky, showcasing a large patio area with arched columns. Lush green grass surrounds the structure, framed by trees, creating a peaceful outdoor setting for relaxation.

4BR home, dog friendly and has indoor pool

Private, pet-friendly home rentals

4.97 out of 5 average rating, 144 reviews

The exterior of the cozy cabin is shown with a welcoming door framed by warm outdoor lights. Two metal chairs and a small table are placed on the patio, scattered with autumn leaves. The surrounding trees hint at a tranquil wooded setting.

Cabin in Cripple Creek

Lucky Llama A-Frame|Views |Fireplace|Dogs Welcome!

4.94 out of 5 average rating, 739 reviews

A charming log cabin is framed by lush greenery, displaying a welcoming front porch with hanging plants. The structure features natural wooden logs, a gray roof, and a stone pathway leading to it. Nearby trees provide a sense of privacy and seclusion.

Cabin in Manitou Springs

Keithley Pines Bristlecone Cabin

5 out of 5 average rating, 144 reviews

Family Getaway: HotTub, Views, Stars, Games, Pets

A circular wooden sauna sits on a raised deck surrounded by trees. Blue adirondack chairs are arranged around a fire pit with glowing flames. The natural setting creates a peaceful atmosphere for outdoor relaxation.

4.88 out of 5 average rating, 280 reviews

𓃵Moose Cabin𓃵 Sauna┃Firepit┃Woodstove┃Corn hole

Guesthouse 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.

4.94 out of 5 average rating, 253 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.

4.96 out of 5 average rating, 137 reviews

Chipita Park Creekside Retreat

Guesthouse in Colorado Springs

A modern living area features a large window that allows natural light to brighten the space. A comfortable leather sofa is complemented by a stylish coffee table and a cozy armchair. A television is positioned nearby, against a backdrop of light-colored walls and decorative artwork.

4.99 out of 5 average rating, 217 reviews

New Luxury 1 - Bed Near Downtown

The exterior of a charming cabin is depicted during twilight, showcasing a red metal roof and brick accents. Large windows offer a warm glow from inside, while the surrounding greenery provides a natural backdrop. A wooden deck invites relaxation as the sun sets in the distance.