Holiday houses in Ivywild

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Top-rated holiday rentals in Ivywild

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

The open living area showcases a stylish leather sofa paired with a wooden coffee table, complemented by decorative cushions. Natural light floods the space through skylights and windows. A fully equipped kitchen is visible in the background, along with a cozy dining area.

Guesthouse in Colorado Springs

4.98 out of 5 average rating, 119 reviews

Earthy Chic Casita in Prime Location

Escape to Cheyenne Casita, a newly-built, stylish, cozy, 1 bed/1 bath home. Perfectly nestled near the mountains in a vibrant, historic neighborhood in a prime location. Whether you are looking for ideal hikes, historic landmarks, or want to indulge in the best local cuisine, you are near it all. Ideal for couples, business visitors, or solo travelers—this inviting space offers the perfect blend of convenience and tranquility. Cheyenne Casita is a safe space for everyone. Permit ASTRP23-1224

Top Guest favourite

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.

Home in Colorado Springs

4.95 out of 5 average rating, 398 reviews

Wildflower Cottage | Fenced Yard | 1 mile D-Town

★ " What a beautiful cottage! A lot of effort was clearly made to make this space resonate homey comfort!" ☞ Pet friendly ☞ Fully fenced backyard w/ dog door ☞ Walk, Bike or Drive 1 mile downtown ☞ 5 mins walk → Memorial Hospital, USOTC, Memorial Park ☞ Fully fenced backyard ☞ Back patio dining, charcoal BBQ, hammock ☞ SmartTV ☞ 18 mins to Garden of the Gods, C/S Airport, Manitou ☞ Fully equipped kitchen ☞ Private parking Perfectly sized for 2 guests and a kiddo. Human and/or the furry kind!

Guest favourite

The dining area features an antique wooden table surrounded by six elegantly designed chairs. A patterned rug adds warmth to the space, while a large window allows natural light to brighten the room. A guitar rests against the wall, accompanied by a decorative lamp and a potted plant.

Home in Colorado Springs

4.94 out of 5 average rating, 577 reviews

Bohemian Dream ★Hot Tub★Bike Downtown★Fire pit★

★Five Star cleaning team trained in disinfecting & sanitation ★Attractively located on the west side, 1 mi to downtown ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Fenced in backyard w/pergola, firepit, hot tub & grill ★Vintage typewriter & record player w/record selection ★BRAND NEW★ comfortable beds! ★Equipped kitchen w/blender, toaster, coffee maker, etc ★FAST WIFI & bluetooth speaker for BUSINESS TRAVEL ★50” Roku TV in living room, Hulu, Netflix, DVD ★Free Colorado soda

Superhost

A welcoming living room features a comfortable gray sofa with accent pillows, a wooden coffee table, and a decorative rug. A large circular mirror hangs on the wall, and windows provide natural light to the space. An adjoining area with a hanging chair is visible.

Home in Colorado Springs

4.82 out of 5 average rating, 273 reviews

Walk|Shop|Dine Ivy Wild Bungalow

☞ Walk Score 85 (Walk to Creekwalk shopping center, cafes, dining, etc.) ☞ Pet friendly (fenced in side-yard!) + views of Pikes Peak ☞ 50" Smart TV ☞ Primary King Bedroom ☞ Pull out sofa in livingroom (full size). Chair in Office Converts to Twin Sleeper ☞ Fast wifi & Private workspace 5 mins → Broadmoor Hotel 7 mins → Downtown Colorado Springs/Colorado College 10 mins → Hiking trails at Cheyenne Canyon 15 mins → Garden of the Gods / Manitou Springs / USAFA 20 mins →Colorado Springs Airport ✈

Guest favourite

A living area is presented with a wall-mounted television displaying streaming options. A comfortable black sofa and a red ottoman are visible. Natural light enters from a nearby window, illuminating a small desk with a chair. A cozy electric fireplace provides warmth to the space.

Guest suite in Colorado Springs

4.95 out of 5 average rating, 369 reviews

The Haven at Ivywild

Enjoy staying in a modern hideaway nestled in the heart of the Ivywild neighborhood. Walk just 1 block down to the popular Ivywild School. Drive 5 minutes to downtown, and less than 10 minutes to Cheyenne Cañon, the Broadmoor, the zoo, Old Colorado City and Manitou. You're in an ideal spot to explore much of the fantastic food, drink, hiking, and sights that CO Springs has to offer. Or sit back and enjoy a beautiful view of the front range mountains while relaxing on the patio. Permit: STR-0691

Top Guest favourite

The exterior of the cottage features a grey facade with large windows and a welcoming front door. A wooden deck with two chairs and a small table is visible, surrounded by gravel landscaping and bordered by a wooden fence.

Cottage in Colorado Springs

4.96 out of 5 average rating, 161 reviews

The Cottage Downtown

This adorable cottage is a newer build Downtown. Featuring an open concept living room connected to a full size kitchen. Overlooking this space you will find a cozy loft w/ a comfy king mattress. Further into the space you’ll find a washer & dryer then the bathroom with a tub/shower combo. Finally you’ll have plenty of space to unpack in the bedroom before drifting off in the inviting queen bed. Enjoy mountain view’s from the entire cottage, deck, or anywhere in the beautifully landscaped yard.

Top Guest favourite

The kitchen features modern appliances, including a refrigerator and coffee maker. A spacious island with a light quartz countertop serves as a dining area. Illuminated pendant lights hang overhead, and a comfortable seating area is visible across from the kitchen.

Guesthouse in Colorado Springs

4.94 out of 5 average rating, 538 reviews

Hillside cottage retreat. Walk to downtown!

Walking distance to downtown our cottage has everything you need for a comfortable stay. King size bed in upstairs bedroom that has its own TV, sitting area and large closet. Main level has a well equipped kitchen with cooktop, counter top over, microwave and instant pot air fryer/pressure cooker combo. Washer and dryer in kitchen. Each level has its own AC/heat units. Outside we have easy parking and a large patio with gas grill. Easy base camp to see everything the Springs has to offer.

Top Guest favourite

The entrance features a bright yellow exterior with blue accents, including a door framed by two potted plants. A spacious wooden deck with stairs is shown, bordered by a white railing and surrounded by greenery, creating a welcoming outdoor space.

Bungalow in Colorado Springs

4.95 out of 5 average rating, 193 reviews

The Cozy Yellow Cottage

Tucked away in a mostly quiet alley in a super eclectic neighborhood, this tiny house was built before 'Tiny Houses' were even a thing. This remodeled and charming 626.5 square foot house is ALL YOURS! Close to downtown Colorado Springs, Ivywild School, the Caffeinated Cow, a library, restaurants, shopping, hiking and biking trails, leisurely and safe neighborhood walks- the sky is truly the limit on what adventures await you! City of Colorado Springs Short Term Rental Permit #A-STRP-22-0086

Guest favourite

The exterior of a historic Queen Anne Victorian home is showcased, featuring a prominent tower and multiple gables under a clear blue sky. The wrap-around porch is adorned with railing, while lush green trees and a well-maintained lawn frame the property.

Guest suite in Colorado Springs

4.95 out of 5 average rating, 358 reviews

Camden Suite | Walk to Downtown & CC

Permit# A-STRP-22-0163 The Cottage is a duplex located adjacent to a beautiful Queen Anne Victorian built in 1889, with all the charm and character. It's two blocks south of Colorado College, walkable to downtown Colorado Springs, restaurants and dining, nightlife, public transportation, and a 5-min drive to Old Colorado City. You’ll love the neighborhood, walkable to the 5-min urban city center, and private entrance. Our place is good for couples, solo adventurers, and business travelers.

Top Guest favourite

Cabin in Cascade-Chipita Park

4.99 out of 5 average rating, 250 reviews

Serene Riverside Cabin: Hot Tub, Fire Pit, Patio

With a river in the backyard next to the private hot tub and massive gas fire pit for all of your party, what more could you need?! If you love watching local wildlife cross over a creek on a luxurious back patio that’s perfect for all seasons, then you should book here. Enjoy the full amenities of a kitchen stocked with a curator’s touch, heated towel rack, remote control gas fireplace, gas grill, 2023 top-to-bottom remodel. Book RiverHouse North, by Forest & Peak Retreats, today!

Top Guest favourite

Bungalow in Colorado Springs

4.98 out of 5 average rating, 157 reviews

Luxury Escape at 5-Star Madison House in Colorado

Welcome to our charming, beautifully renovated 2BR/1BA retreat in the historic Old North End! Perfect for couples and pet lovers, our home features styled concrete flooring, luxury linens, a spa-style bathroom, arcade games, a fenced yard, and more. Walk to downtown, parks, and Colorado College! A $250 security deposit will be collected before arrival and refunded 2 days after checkout, provided there is no damage. Enjoy complimentary wine, chocolate, and a truly memorable stay!

Top Guest favourite

The exterior of the home features a vibrant blue facade with contrasting red accents. A welcoming porch with a couple of chairs invites relaxation. A landscaped yard with pebbles, a small garden area, and a winding pathway enhances the curb appeal.

Apartment in Colorado Springs

4.94 out of 5 average rating, 521 reviews

★OCC Hideaway★Firepit, Grill, Backyard + Firestick

★Minutes to Garden of the Gods and so much hiking! ★Attractively located on the west side, 1 mi to downtown OCC, 1.5 mi to downtown COS ★Short drive to CO College, Manitou Springs, Pikes Peak, USAFA ★Fire pit & grill ★BRAND NEW★ comfortable bed! ★Fully equipped kitchen w/blender, toaster, coffee maker, etc ★BUSINESS TRAVEL: FAST WIFI, Alexa, phone charging station, keyless entry ★FAMILY FRIENDLY: Pack N Play & High chair ★TV w/Amazon firestick (Hulu/Netflix) ★FREE Colorado soda