Guest house holiday rentals in Colorado Springs

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

Private Carriage House | Walk to downtown & CC

Permit# A-STRP-22-0164 The Carriage House is located on a beautiful property adjacent to an 1889 Queen Anne Victorian, loaded with charm and character. It's two blocks south of Colorado College, walkable to downtown Colorado Springs, restaurants and dining, nightlife, public transportation nearby, and a 5-min drive to Old Colorado City. You’ll love the neighborhood, walkable to the urban city center, and private entrance. Our place is good for couples, solo adventurers, and business travelers.

Charming Guesthouse in Historic Old Colorado City!

Nestled in a peaceful, tree-lined neighborhood, this cozy guesthouse is just minutes from downtown Colorado Springs or the heart of historic Old Colorado City. Enjoy the nearby local shops, restaurants, galleries, & more. Perfect for couples or solo travelers looking for a relaxing base to explore the city. Whether you're here for outdoor adventures, a romantic getaway, or a quiet retreat, you’ll feel right at home. No pets, smoking, parties, or events. Guests must be 21+ with ID on profile.

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.

A Retreat in the Woods by a Lake & Mountain Views!

Detached guesthouse with private entrance and deck sleeps 2 ADULTS in huge king size bed + 2 KIDS in loft. Located 2 blocks from PINECREST WEDDING VENUE. Hiking trails, access to Nat'l Forest + mountain reservoir. Tennis court in backyard. Pickle ball rackets provided!Open space in back Palmer Lake is 2 mins away, 2 adult SUPs available to you. Great fishing! Shared (but private) space includes a hot tub, fire pit. A/C available May-September. No smokers, marijuana, or vape users. No pets.

Cheyenne Cottage | Mins from Broadmoor + hiking

Nestled quaintly in Cheyenne Canyon, the location of the cottage is perfect for those looking for an ideal Colorado getaway! The Broadmoor is just a 5 min drive or 15 min walk. Down the road is Cheyenne Mountain Zoo, Seven Falls & Stratton Open Space. You will have access to the some of the best hiking trails! Very close to I25, Manitou Springs, Old Colorado City and downtown. Don’t miss out on this beautiful location, near everything Colorado Springs has to offer! STR Permit- R-STRP-25-0015

Across from the Park with Fenced Yard and Hot Tub

★Directly across Memorial Park - Velodrome, Play Sets, ice skating, walking trail around lake, YMCA Rec Ctr w/swimming/fishing ★Walk 0.5 mi to local Switchback coffee ★1.3 mi to dwntwn COS ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Fenced in yard w/firepit, grill, hot tub + yard games ★New king bed ★55" Roku TV w/Apps ★Fast WIFI ★Equipped kitchen: Waffle maker, blender + more! ★FAMILY FRIENDLY: Pack n play, baby bath, high chair, baby monitors, toys ★Free Colorado soda

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.

Colorado’s Cozy Corner cottage in mountains

Colorado’s Cozy Corner is a cute home that is close to everything, making it easy to plan your visit. The photos on the walls will inspire you, featuring incredible places in the springs you can visit. While the decorations and modern style of the space will leave you excited to come home after your adventures. This home has two bedrooms, a full bathroom, a full kitchen, a nice living space to relax in, outdoor picnic table and fire pit! It is located in a quiet neighborhood. A-STRP-24-0213

The Happy Cottage - Historic Downtown Dairy

Step into history at this beautifully restored cottage, once the original hose house of the early 1900s Sinton Dairy. Tucked behind the main home, this unique retreat blends historic charm with modern comfort. Enjoy a cozy bedroom with luxury linens, a full bath, and a fully stocked kitchen. Unwind with fast WiFi and free parking included. Located minutes from downtown Colorado Springs and I-25, it’s the perfect mix of character, comfort, and convenience for a memorable stay. Permit #STR0253

Walk to Garden of the Gods | Hot Tub | Epic Views!

Enjoy stunning views of the sun setting behind Pikes Peak through floor-to-ceiling windows! Sip your morning coffee on the private patio as a family of deer wander by. Walk into the Garden of the Gods and then relax in the hot tub beneath the stars. Prepare a delicious meal with everything you need already provided for you; cookware, oils, and spices - and enjoy it with mountain views as your backdrop Discover your ideal Colorado Springs retreat in my lovingly renovated historic guesthouse!

*Walk Downtown* | Cozy Sunroom | Fiber WiFi

Experience the beauty of downtown Colorado Springs in this stunning, private guest house packed with everything you need! ☕️🚶‍♂️ QUICK 5-10 minute WALK downtown to restaurants, stores, bars + coffee shops ⛰️ Quick drive to Garden of the Gods, Pikes Peak, & USAFA! 👩‍💻 Fast Fiberoptic WiFi w/ dedicated workspace, & Smart TV 🧑‍🍳 Fully-stocked kitchen! 🅿️ Free Diagonal Street Parking in front of House 👕 Washer/Dryer in house 🔥❄️ Brand new HEAT/AC with room by room climate control