Pet-friendly vacation rentals in Woodland Park

The sauna interior features warm wooden walls and a bench arrangement, accentuated by natural light entering through a window. A stainless steel bucket and ladle are positioned nearby, along with neatly rolled towels. A mirror and shelf provide functional spaces, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 134 reviews

Sauna, Forest + Mtn Views - Cabin Under The Stars

Retreat in the mountains of Colorado at this private two-bedroom, two-bath cabin with a steam sauna. Surrounded by Ponderosa Pines and Aspens in the beautiful Pikes Peak region, come unwind and recharge. This home is located in a nationally registered dark sky zone, and offers gorgeous mountain views from the porch. The cabin boasts an open living room, fully equipped kitchen, and inviting dining area. The space was designed and outfitted so you can enjoy all the comforts of your own home, while

4.98 out of 5 average rating, 170 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.

Place to stay in Woodland Park

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.

4.99 out of 5 average rating, 136 reviews

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.

4.98 out of 5 average rating, 107 reviews

The chalet's A-frame structure is framed by tall pine trees, showcasing large windows that invite natural light. A gentle plume of smoke is rising from the chimney, indicating a warm interior. The outdoor deck offers a seating area for relaxation amidst a scenic mountain setting.

Cabin in Woodland Park

Fireplace, Hot Tub, 2 Decks, Scenic Vws, Dogs YES

Escape to the “Blue Spruce Chalet”. A redesigned, 900 sq. ft. A-frame (ish!) retreat on 2+ private acres in Manitou Experimental Forest, 15 mins north of Woodland Park & steps away from world-class trails & fishing. Explore the outdoors or plan to stay in. Enjoy fast Wi-Fi, a fully equipped kitchen, a wood-burning stove, an outdoor firepit, & 2 decks with stunning mountain & sunset views. Star gaze from the hot tub. You may never want to leave this slice of heaven. Perfect for a quick getaway.

4.93 out of 5 average rating, 119 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.

4.92 out of 5 average rating, 181 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!

Guesthouse 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.

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, 579 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, 416 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, 397 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!

Popular amenities for Woodland Park pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

The exterior of a modern black house is shown, featuring a metal roof and large windows. A concrete driveway leads up to the entrance, accompanied by an outdoor seating area with chairs and a fire pit. Surrounding greenery adds a natural touch.

4.96 out of 5 average rating, 214 reviews

Casita Noir | King Bed | Fireplace | Private Patio

4.94 out of 5 average rating, 121 reviews

Charming Home with Mountain Views & Sunny Patio

A serene bedroom features a comfortable bed dressed in crisp linens, flanked by two bedside lamps. An artistic mountain mural adorns the wall behind the bed, complemented by a decorative throw along the foot. A cozy accent pillow adds a touch of warmth.

4.86 out of 5 average rating, 277 reviews

»Near Dwntwn + CC« King Beds┃Trail Access┃Firepit

4.99 out of 5 average rating, 218 reviews

The Little House at RRCOS -Escape- Amazing views!

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, 252 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.

4.9 out of 5 average rating, 442 reviews

Rockrimmon Retreat Hottub - FirePit - Dog Friendly

4.93 out of 5 average rating, 235 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

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.

4.92 out of 5 average rating, 256 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, 185 reviews

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

Apartment in Colorado Springs

1BR Luxury Apartment Pet Friendly with Heated Pool

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 bird's eye view captures the welcoming ambiance of Green Mountain Falls, featuring a charming, low-rise building alongside a well-maintained road. Vehicles are parked conveniently nearby, and the surrounding hills are lush, offering a picturesque backdrop of nature.

5 out of 5 average rating, 46 reviews

Guests Rave: Best Location + Wildlife

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.

4.97 out of 5 average rating, 34 reviews

King's Oasis

A serene lake scene showcases a central fountain spray amidst a backdrop of gently sloping mountains. Four ducks swim leisurely near the shore, while a pavilion with a peaked roof is visible along the bank, surrounded by trees and picnic areas.

Cabin in Cascade-Chipita Park

4.67 out of 5 average rating, 12 reviews

FOUR SEASON MOUNTAIN RETREAT W/VIEW BY CO SPRINGS

Private, pet-friendly home rentals

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.

4.97 out of 5 average rating, 235 reviews

New Luxury 1 - Bed Near Downtown

Apartment 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.

4.95 out of 5 average rating, 783 reviews

Downtown Old Colorado City with Panoramic Views

A modern A-frame cabin is nestled in a snowy landscape, showcasing a spacious deck and a luxurious hot tub. Nearby, a geodesic dome offers a unique stargazing experience. The backdrop features a starry sky, enhancing the serene mountain setting.

4.98 out of 5 average rating, 103 reviews

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

A spacious outdoor seating area is presented on the deck, featuring a fire pit surrounded by comfortable wicker chairs and a sofa. The lush forest serves as a backdrop, providing a serene atmosphere under a clear blue sky.

4.93 out of 5 average rating, 102 reviews

Stargazing Cabin, Hot Tub, Fire Pits, Mntn Forest

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

A modern cabin with a distinctive gable roof is set against a backdrop of trees. A flag is displayed on the porch, while green grass surrounds the structure. Large windows allow natural light to brighten the interior, and a gravel path leads to the entrance.

4.83 out of 5 average rating, 108 reviews

Lake George Cabin

Guest suite in Colorado Springs

A cozy basement suite is presented, featuring a sectional couch and a wall-mounted television. Shelves filled with books occupy one wall, while a dry bar with seating is visible nearby. Soft lighting contributes to a relaxed ambiance within the space.

4.94 out of 5 average rating, 306 reviews

Private, Spacious Basement Suite in N CO Springs