Pet-friendly holiday rentals in Woodland Park

4.98 out of 5 average rating, 174 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, 141 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.

Guest suite in Cascade-Chipita Park

A private outdoor area features a hot tub surrounded by a leafy plant and softly lit with string lights. A small table and two chairs offer a cozy space for relaxation, with a colorful wall hanging adding a warm touch to the ambiance.

4.82 out of 5 average rating, 274 reviews

Private Hot Tub, Sauna & Mountain Views

Winnemucca Spa's guest suite is a completely private experience with its own entrance, hot tub, wet sauna, and stunning Rocky Mountain views. Designed as a peaceful adults-only retreat, the suite is ideal for couples looking for a romantic escape or a quiet basecamp for exploring the Pikes Peak region. Whether it’s hiking forest trails, catching live music in the funky town of Manitou, or standing in awe at the towering red rocks of Garden of the Gods… the mountains are calling. Welcome home.

4.92 out of 5 average rating, 182 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, 178 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.

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, 145 reviews

Grandview 3BR Mountain Cabin w/ Hot Tub & EV

Escape to Grandview: Your Mountain Getaway Awaits! Nestled in the charming town of Green Mountain Falls, this stunning 3BR retreat offers the perfect blend of comfort and adventure. Enjoy breathtaking mountain views through expansive picture windows and unwind in the large covered hot tub after a day of exploring. With an EV charger on-site, you’re road ready! Ideally located: ✨ 20 mins to Colorado Springs ✨ 12 mins to Manitou Springs ✨ 5 mins to Woodland Park Your perfect mountain escape!

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, 583 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 🤗

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.

4.97 out of 5 average rating, 226 reviews

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 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.

4.88 out of 5 average rating, 420 reviews

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 exterior of the chalet is illuminated by warm string lights at dusk, showcasing a wood and glass structure surrounded by trees. A soothing hot tub is visible on the deck, offering a perfect spot for relaxation under the evening sky.

4.98 out of 5 average rating, 110 reviews

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

Escape to the “Blue Spruce Chalet”. A 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 a fully equipped kitchen, a wood-burning stove, an outdoor firepit, 2 decks with stunning mountain & sunset views and reliably fast WiFi. Star gaze from the hot tub. You may never want to leave this slice of heaven. Perfect for a quick getaway.

4.99 out of 5 average rating, 405 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).

5 out of 5 average rating, 400 reviews

Cabin in Divide

Black Ridge Cabin|Private Hot Tub & Forest Retreat

The Black Ridge Cabin - Your cozy mountain escape! 🗻Tucked in Colorado’s STUNNING Pikes Peak region 🛏️ Cozy 2BR w/queen beds on 1 private acre 🌌 Secluded hot tub under the stars 🔥 Indoor Fireplace + fast Starlink Wi-Fi 🍳 Stocked kitchen + washer/dryer 🌲Near hiking trails & hillside access with fenced yard 🚗 20 mins to Woodland Park, 2 hrs to DIA 🚶‍♂️ Walk to scenic Burgess Reservoir (no lake access) 🔥 Fire pit, outdoor dining, forest views 🅿️ Covered carport + driveway parking

Popular amenities for Woodland Park pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A spacious living room is accented by warm leather seating and natural light streaming through large windows. A decorative stone fireplace stands opposite a flat-screen TV, while artwork and a cozy rug add inviting touches to the neutral-toned decor.

4.94 out of 5 average rating, 166 reviews

Canyon Retreat! 3min to Broadmoor. Hot Tub!

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, 198 reviews

Private Guest House in the Forest

4.95 out of 5 average rating, 128 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

4.99 out of 5 average rating, 220 reviews

Home in Manitou Springs

The Little House at RRCOS -Escape- Amazing views!

Home in Cascade-Chipita Park

4.91 out of 5 average rating, 160 reviews

Recharge at this wonderful cabin in the mountains

The kitchen features wood cabinetry and granite countertops with a modern stainless-steel refrigerator and microwave. A double oven is installed beneath the countertop. The adjacent dining area showcases a wooden dining table surrounded by curved-back chairs, providing a welcoming space for meals.

4.98 out of 5 average rating, 321 reviews

The Memory Maker! 2 King Beds + Garage & Hot Tub!

Home in Old Colorado City

A bright kitchen features green cabinetry that enhances the space's vibrant atmosphere. Natural light streams through a window above the sink, illuminating tiled surfaces. An organized countertop showcases appliances and decorative items, while a dining table stands nearby, complemented by a potted plant.

4.89 out of 5 average rating, 474 reviews

Recording Studio Duplex in Old Colorado City

4.93 out of 5 average rating, 236 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!

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 37 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, 258 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, 187 reviews

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

5 out of 5 average rating, 3 reviews

4BR home, dog friendly and has indoor pool

Cabin in Garden of the Gods

4.79 out of 5 average rating, 24 reviews

Timber Lodge #2

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: Super Clean + Location

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, 36 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

4.94 out of 5 average rating, 747 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

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, 148 reviews

Chipita Park Creekside Retreat

4.98 out of 5 average rating, 255 reviews

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.

Cabin in Florissant

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

4.95 out of 5 average rating, 139 reviews

A wooden cabin with a wraparound porch is set amidst snow-covered pines. Large windows reflect warm light from within. The surrounding landscape features a gentle slope, enhancing the secluded feel of the property.

Cabin in Florissant

Top of The Mountain Ranch Cabin in Florissant

4.94 out of 5 average rating, 359 reviews

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.

Cabin in Divide

Pinecone Retreat | Hot Tub, Fire Pit & Mtn Views

Cabin in Green Mountain Falls

The cabin is nestled among greenery, featuring brown wood siding and a prominent stone chimney. A stairway leads up to a wrap-around deck, offering views of the surrounding trees and mountains. Tall pines frame the structure, enhancing the natural setting.

4.97 out of 5 average rating, 129 reviews

Decks+Views+Hot Tub+Fireplaces

Superhost

A two-story log cabin is illuminated at dusk, showcasing warm light shining through multiple windows. A stone pathway, bordered by stepping stones, winds gently up the grassy hill leading to the home, which is surrounded by trees.

4.83 out of 5 average rating, 102 reviews

The Sleeping Bear Lodge, Hot Tub/game room.