Family-friendly holiday rentals in Colorado Springs

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!

Cabin on Pikes Peak, Hot tub, Walk to Wine + Food

*Brand new nordic spa 6 person hot tub as of April 2026!* 2 bedroom, 2 bath historic cabin backs to wilderness. Enjoy amazing views of the surrounding trees and rocks. Located on Pikes Peak, Hidden Falls cabin is just 10 minutes from Manitou and Colorado Springs but it feels like a world away. Take in the views from your soak in the hot tub or under the outdoor shower. Walk to the Wines of Colorado for libations and food. The cabin is an ideal destination for a restful retreat, a romantic getawa

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

The Enchanted Hobbit Cottage

An extraordinarily special place. Serene & Peaceful - Seclusion while still only a few miles to Colo Springs & attractions. Pet & everything friendly. Your cottage sits on your own 3 acres, 10 acres to explore. Everything you need for a solo couples retreat. There are playful touches everywhere (you’ll have to see it to understand). Specifically designed and built by your host – to enhance inspiration and vision. Not just pretty words, that’s the truth. Ron‘s first and foremost, an artist.

𓃵Moose Cabin𓃵 Sauna┃Firepit┃Woodstove┃Corn hole

►Location: Short drive to CO Wolf + Wildlife Ctr, award-winning Paradox Beer Co, Fossil Beds, Lake George, Mueller State Park, Pikes Peak, Garden of the Gods ►OUTDOORS: Nearby hiking, biking, snowshoeing, horseback riding, cross country skiing, rock climbing, rafting ►DINING/CASINO: Short drive to Cripple Creek + Woodland Park ►YARD: picnic table, grill, yard games, barrelwood SAUNA + firepit ►FAMILY FRIENDLY: Pack n play, high chair, monitors, toys + more! ►Equipped Kitchen ★WAFFLE MAKER★

Riverside Retreat: Sauna, Hot Tub & Fireplace

With a river in the backyard next to the private hot tub and sauna, what more could you need? If you love watching local wildlife, listening the sound of the creek, and relaxing on a luxurious back patio that’s perfect for all seasons, then RiverHouse South by Forest & Peak Retreats is for you! Enjoy the full amenities of a kitchen stocked with a curator’s touch, heated towel rack, remote control gas fireplace, top-to-bottom remodel. Book RiverHouse South, by Forest & Peak Retreats, today!

Modern A-Frame w/ Hot Tub + Stargazing Dome

✦ Newly built modern A-frame (750 sq ft) in the Pikes Peak Region ✦ Two cozy bedrooms (including loft) ✦ Luxurious private jetted hot tub ✦ Stargazing dome ✦ Picturesque wooded lot w/ serene views ✦ Easy access to the Fossil Beds, three state parks, national forest, hiking, gold-medal fly fishing, & much more ✦ Large deck w/ gas fire pit, cushioned Adirondack seating, & outdoor dining ✦ Indoor gas fireplace ✦ Full kitchen w/ coffee & tea bar ✦ Weber BBQ grill ✦ Pet friendly (one dog max.)

Walk to Old CO City, King Bed, Fenced in Hot Tub

★Attractively located on the west side, 0.7 mi to downtown OCC, 1.5 mi to downtown COS ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Fenced in yard with fire pit & grill and hot tub ★BRAND NEW★ comfortable beds! ★Fully equipped kitchen w/blender, toaster, coffee maker, etc ★BUSINESS TRAVEL: Desk area, FAST WIFI, Alexa, charging cables, keyless entry ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, monitors, toys + more! ★Large Smart TVs ★FREE Colorado soda

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!

Historic Craftsman ★ Fire pit┃Waffle Maker┃Near CC

✓LOCATION: Walk to Switchback Coffee┃1.0 mi to Colorado College┃1.5 mi to downtown┃Short drive to Garden of the Gods, Pikes Peak, USAFA ✓OUTDOORS: Sit under the string lights on a private fenced in patio w/smokeless firepit & grill ✓ENTERTAINMENT: Movie loft & living room w/Roku TVs, fast WIFI & games ✓EQUIPPED KITCHEN: Keurig, Chemex, waffle maker, blender, etc ✓FAMILY FRIENDLY: Pack N Play, high chair, stroller, toys, monitors +more ✓Mountain views ✓Complimentary local soda

Mountain views! Hot Tub! Downtown! Pet friendly!

This house is the perfect home base for those who want to explore Colorado Springs! Located just minutes from downtown, you will be close to many restaurants, shops, coffee houses, and entertainment. The home is perfect for a couple or a solo traveler. You'll love the recently refinished kitchen, big backyard, fire pit, and mountain views! Less than 15 from Garden of the Gods, Seven Falls, Red Rock Open Space, Manitou, Pikes Peak, and Old Colorado City. A-STRP-23-0408

Off-grid, Earthen home in the forest!

*PLEASE READ FULL DESCRIPTION BEFORE BOOKING!* An eco friendly, self sustaining, off-grid Earthship home nestled into the Black Forest of Colorado Springs. A place to ground, disconnect, and fully immerse yourself in the beauty that is Colorado. This plant filled, handcrafted home is pure magic and unlike any other stay you've experienced and we are honored to share her with you. 🤗 "The richness I achieve comes from nature, the source of my inspiration" -Monet