Pet-friendly holiday rentals in Woodland Park

4.98 out of 5 average rating, 163 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, 130 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!

4.93 out of 5 average rating, 111 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, 223 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, 564 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.

4.88 out of 5 average rating, 410 reviews

The cabin's exterior showcases rustic wooden logs juxtaposed with modern elements. A welcoming red door is surrounded by simple landscaping, including a bench and a small tree. The entrance provides a view of the nearby road and surrounding trees, adding to the cabin's quaint charm.

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

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).

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!

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.

4.93 out of 5 average rating, 198 reviews

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!

A rustic log cabin with a green metal roof is surrounded by tall trees, partially covered in snow. A small porch area is visible, featuring seating arrangements and a grill. The cabin's natural wood exterior reflects its historic charm amidst a serene winter landscape.

4.96 out of 5 average rating, 314 reviews

Best Li'l Bunkhouse on 40 Wooded Acres

This log cabin is one of four built in the late 40s or early 50s. Part of the original homestead, the cabin was renovated with reclaimed materials but updated for modern comfort. Old world charm, trim repurposed or locally milled. Located on 40 wooded acres, this is the perfect place for solitude and yet close to amenities and attractions. Sleeps 4, dining and kitchen area, dogs welcome

Popular amenities for Woodland Park pet-friendly home rentals

Kitchen

Wifi

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, 193 reviews

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

The bedroom features a spacious bed adorned with a soft green blanket and decorative pillows. Flanking the bed are two bedside tables with lamps. Above, three framed art pieces depict cacti, complementing the natural light streaming through the window.

4.9 out of 5 average rating, 230 reviews

Alpaca Adobe: Hot tub, Couples hammock & Fire pit!

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, 183 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

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, 335 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.

4.93 out of 5 average rating, 243 reviews

Beautiful mountain getaway with hot tub!

A single-story home features a light-colored exterior with a contrasting blue entrance door. A paved driveway leads to a two-car garage. The well-maintained front yard includes green grass and decorative shrubs, while a small seating area is positioned near the front porch.

4.89 out of 5 average rating, 431 reviews

Rockrimmon Retreat Hottub - FirePit - Dog Friendly

4.96 out of 5 average rating, 125 reviews

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

Pet-friendly home rentals with a pool

5 out of 5 average rating, 31 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

4.91 out of 5 average rating, 232 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, 181 reviews

Stylish NEW Home Close to Downtown

Cabin in Garden of the Gods

A cozy cabin bedroom features warm wooden paneling and vibrant red accents. A spacious bed with a patterned throw is complemented by a kitchenette equipped with modern appliances. Natural light flows in, illuminating the room’s rustic charm and inviting atmosphere.

4.9 out of 5 average rating, 10 reviews

Timber Lodge #24

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

Private, pet-friendly home rentals

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

4.96 out of 5 average rating, 277 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

5 out of 5 average rating, 144 reviews

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

4.91 out of 5 average rating, 262 reviews

A comfortable living area features wooden walls and high ceilings. Natural light floods through large windows, offering views of the surrounding nature. Seating options include a cozy sofa and armchairs, and a rustic coffee table sits in the center. A bookshelf holds various entertainment options.

Cabin in Cripple Creek

Private Mountain Retreat up to 8 - Hot Tub & Dogs!

A saltwater hot tub sits on a deck, offering a calming view of the surrounding mountains and dense forest. Soft blue light reflects off the water, creating a serene atmosphere. The horizon features a clear sky, enhancing the sense of tranquility in this secluded setting.

4.98 out of 5 average rating, 241 reviews

Mydnyt Mtn Cabin w/Loft Private Hot Tub/No Chores

Guest house 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, 219 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.

4.94 out of 5 average rating, 344 reviews

Mountain charm -Hot Tub, pups, mtn. views