Pet-friendly vacation rentals in Woodland Park

4.98 out of 5 average rating, 152 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.

4.99 out of 5 average rating, 156 reviews

An open-concept kitchen and dining area feature wood-paneled walls with triangular skylights allowing natural light to fill the space. A modern kitchen is equipped with a stainless steel refrigerator and oven, with black cabinetry enhancing the design. A round dining table is adorned with a potted plant.

Cabin in Florissant

Modern A-frame w/ hot tub + view

Escape the city in this beautiful Scandinavian-inspired A-frame. Sitting on 2 wooded acres overlooking Pikes Peak, Elwood's A-frame has been newly remodeled with top-of-the-line amenities including a hot tub, Norwegian gas fireplace, quality bedding, and a spa-like shower. Relax on the large deck and listen to your favorite music on our Sonos system, play games with friends, read, day trip to lakes and hikes, make memories, refocus, rejuvenate, and relax in this intentionally curated experience.

4.98 out of 5 average rating, 118 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.

4.93 out of 5 average rating, 164 reviews

A cozy living area is presented with a plush sofa and a small dining table. A framed poster titled 'Ride the Trails Colorado' adorns the wall. A pet bed placed near the table indicates a pet-friendly environment, while natural light streams through a window with blinds.

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!

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, 547 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, 214 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, 396 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, 357 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).

The Timber A-Frame cabin is surrounded by snow-covered trees, showcasing a warm wooden exterior. A spacious deck extends from the cabin, offering views of the winter landscape. The peaked roof and large windows reflect the mountain charm of this serene retreat.

4.98 out of 5 average rating, 232 reviews

The Timber A-Frame✦Large Deck✦Hot Tub✦BBQ

Escape to the Timber A-Frame, where luxury meets the untamed spirit of the Rockies. Discover a blend of refined elegance and mountain allure in this magazine-worthy retreat. Crafted with meticulous detail, this stylish cabin offers a sanctuary of comfort and sophistication. Indulge in the hot tub under the vast sky, explore nearby trails, and cozy up to a movie in the vaulted living room by the fire. Your perfect mountain getaway awaits at the Timber A-Frame.

Superhost

A bright and welcoming living area features a light-colored sofa with a cozy yellow throw pillow. A large TV is mounted on the wall opposite a comfortable armchair. Sunlight streams through multiple windows, illuminating a view of the dining area beyond.

Tiny home in Woodland Park

4.87 out of 5 average rating, 274 reviews

Sunny Tiny Haven | BBQ, Fresh Vibes & Peak Views

🏔️ Tiny Oasis | Serenity & Pikes Peak Views Await! 🌲 As featured on Tiny House Expedition, this charming retreat in Peak View Park offers the perfect mix of cozy cottage vibes and woodland tranquility. Nestled on a private drive with towering trees and wildlife, enjoy secluded porch views, BBQ nights, and breathtaking Pikes Peak scenery. After skiing, unwind with cocoa and soak in the peaceful mountain atmosphere. 💫 Book now for your perfect escape!

A cozy cabin is illuminated under a clear night sky filled with stars. Warm lighting accents the exterior, while a fire pit surrounded by wooden chairs offers a space for relaxation and gathering. The surrounding nature enhances the tranquil atmosphere.

4.93 out of 5 average rating, 153 reviews

Wayward Lodge| Hot Tub | Fire Pit | Secluded

Escape to this cozy cabin, nestled among towering trees for a peaceful, secluded feel. Relax in the private hot tub or gather around the fire pit under the stars. Inside, enjoy rustic charm with modern comforts. Watch for visiting wildlife! Just 10 min from Divide and 20 min from Woodland Park, with easy access to trails, restaurants, and local attractions. Adventure and serenity meet at this perfect woodland retreat!

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.