Guesthouse holiday rentals in El Paso County

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.

Location · Value · Quiet

Private Carriage House | Walk to downtown & CC

Permit# STRP-25-0807 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.

Location · Family · Parking

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.

Family · Location · Comfort

New Luxury 1 - Bed Near Downtown

This brand-new build (730 sq. feet) is modern with extra touches of comfort including heated bathroom floors, a smart bathroom mirror, walk-in bedroom closet, vaulted ceilings, and a Rokutv so you can stream your favorite shows. A small private balcony and yard space mean you can enjoy the Colorado sun. Easily access everything Colorado Springs has to offer as this home is a short drive from incredible hiking as well as downtown. Please note: this home is above a garage which is used regular

Value · Location · Hospitality

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

Family · Value · Laundry

✮Downtown Tiny House✮ ✓Fire pit ✓Grill ✓Roku TV

Stay in a converted tiny house that was once a 1900’s Carriage House. ★Five Star cleaning team trained in disinfecting and sanitation ★4 blocks from downtown COS ★Short drive to CO College, Garden of the Gods, Pikes Peak, USAFA ★Newly landscaped backyard with fire pit + grill. Shaded patio with seating ★32" TV with Roku w/apps ★Business Travel: Keyless entry + fast wifi ★Fully equipped kitchenette: hot plate, microwave, mini fridge, pots, pans, Keurig + more! ★FREE Colorado-made soda

Location · Family · Check-in

The Bonnyville Suite

Cozy private suite in Colorado Springs’ Bonnyville neighborhood, conveniently located near downtown and I-25. Enjoy a private entrance, queen bed, full size sleeper sofa, kitchenette, fast Wi-Fi, TV, patio and parking. Close to Garden of the Gods, Pikes Peak, US Air Force Academy, Olympic Training Center, hiking restaurants, breweries, wineries, and shopping. Walk to groceries, coffee and a neighborhood park. Perfect for couples, business travelers, adventures and extended stays.

Location · Value · Comfort

Earthy Chic Casita in Prime Location

Escape to Cheyenne Casita, a 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

Location · Family · Decor

Ivywild Cottage ~ Cozy, Historic, Artistic Retreat

Come disconnect and enjoy artistically-inspired ambiance in SW Colorado Springs' charming historical Ivywild neighborhood. With optimal accessibility to Cheyenne Canyon (5 min), the Broadmoor Hotel (3 min), downtown (10 min) and Manitou Springs (15 min), our cottage is perfect for visitors seeking a unique stay. Situated behind our main house, guests have their own private driveway, outdoor patio area, and entire cottage to enjoy. Also check out our IG page, @ivywild_cottage!

Family · Location · Cleanliness

Cozy Cottage on the Rock Island Trail

Keep it simple at this peaceful and centrally-located place. Stay in this freshly renovated space in a quiet neighborhood just north of downtown Colorado Springs. Located in the peaceful Bonnyville neighborhood, you will be close to shopping, dining, brew pubs, parks, trails, and a PikeRide electric bike hub. The kitchen is well equipped, and has a few basic staples, including coffee. There is a grocery store just two blocks away.

Location · Family · Kitchen

Rustic Bunkhouse in Black Forest

Retreat from civilization in this beautiful log bunkhouse in the forest. Stroll among the ponderosa pines or sit by the lake on our sprawling 40 acres. Only 10 minutes northeast of Colorado Springs and 20 minutes to the heart of the Air Force Academy. This 1 bedroom (queen), 1 bath also has a 5-bed sleeping loft that sleeps 8 (one queen futon, two double, two single top bunks) and a full kitchen.

Location · Family · Bathroom

The Carriage House | Central | Mountain Views

Welcome to your new retreat in downtown Colorado Springs! This modern, stylish, and private guesthouse is nestled in a historic neighborhood. A new build, professionally designed for your comfort, offers walkability to nearby attractions. Embrace the local culture as you explore the downtown scene. Enjoy the perfect blend of old-world charm and modern amenities, making your stay unforgettable.

Value · Family · Amenities