Holiday rentals in Pikes Peak

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Top-rated holiday rentals in Pikes Peak

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Guest favourite

Cottage in Cascade-Chipita Park

4.85 out of 5 average rating, 213 reviews

Mountain Views | Perfect Couples Get Away | Cozy

Charming and newly updated cottage has every amenity of a modern stay with the location and stunning views of a remote mountain retreat. Perfect for friends or couples, the cottage is located at the base of Pikes Peak. 10 minutes away from Colorado Springs or Woodland park you are close to all of the recreation and activities that make the Pikes Peak region special like Cheyenne Mountain Zoo, hiking trails, Pikes Peak Highway, and downtown Colorado Springs You'll love the mountain views.

10–17 Nov

$123 SGD per night

Guest favourite

Tiny home in Colorado Springs

4.96 out of 5 average rating, 619 reviews

Cozy cottage, walk to Garden of the Gods

Welcome to the cozy "Chicken Coop" at the foot of Garden of the Gods park in a quiet corner of the city near the funky downtown and great restaurants of Old Colorado City. Walk out your door into the coolest city park in the country, with miles of hiking through jaw-dropping rock formations. The rustic cottage has a pillow-top bed, kitchenette and renovated bath. Enjoy peace and quiet on the deck. An adventurer's dream place to recover after exploring Colorado's great outdoors. Permit: STR 0186

24 Feb – 3 Mar

$152 SGD per night

Guest favourite

Guest house in Woodland Park

4.98 out of 5 average rating, 100 reviews

Rose Mountain Escape Pet friendly W/pet fee

Rose Mountain escapes has beautiful views of Aspen trees. 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. It is a small cabin with a VERY STEEP STAIRCASE to the bedroom. We have a large deck with Adirondack chairs, a gas fire pit and grill for your use. We have great WiFI. We have kitchenette, washer and dryer. Pet friendly with CLEANING FEE list pet on reservation!

11–18 Nov

$170 SGD per night

Guest favourite

Tiny home in Colorado Springs

4.98 out of 5 average rating, 598 reviews

The Trolley Car in Colorado Springs

Fall in love with OCC while you unwind in this restored trolley car! Your home away from home will give you a quiet night’s sleep in a cozy bed with fresh linens. Prepare your own meals or simply take a short stroll to nearby restaurants and shops. There’s tons for you to do just minutes from the trolley and with so much to explore you’ll be glad you’re close to this space to sit back and relax! You’ll get a small breakfast and snacks to get you going in the morning! I can’t wait to host you!

14–21 Oct

$158 SGD per night

Guest favourite

Guest suite in Woodland Park

5.0 out of 5 average rating, 221 reviews

Private Guest Suite w/Trees & Awesome Peak Views

Picture-perfect Pikes Peak views from your living room, bedroom, and covered patio of this stunning Colorado mountain home's guest suite with a classic Colorado feel. The suite includes the entire walk-out lower-level of our home. It is private, separate, and has its own entrance. With a full kitchen and central location, this is the perfect base-camp for a Colorado get-away; however, with the Ponderosa Pine, Aspen, and hiking trails right up the street, you may not want to ever leave.

5–12 Nov

$150 SGD per night

Guest favourite

Treehouse in Cascade-Chipita Park

4.99 out of 5 average rating, 176 reviews

The Treehouse, Modern Retreat with Panoramic Views

*If booking a stay for Oct.-May please carefully read winter info. Welcome to the Treehouse - the ultimate Colorado getaway. Perched high in the trees with panoramic views, you’ll never want to leave. This completely remodeled, octagon treehouse is just 15 minutes from most attractions in Colorado Springs and 5 minutes from the famous Pikes Peak Highway and gorgeous hiking trails - you are right in the middle of plenty to do while also being tucked away in your own little forest paradise.

15–22 Apr

$640 SGD per night

Guest favourite

Cabin in Divide

4.95 out of 5 average rating, 144 reviews

Cozy A-Frame with Stunning Views of Pike's Peak

Adorable A-frame cabin with stunning views of Pikes Peak. Quaint but not too remote. Close to numerous hiking trails, fishing, and other outdoor activities. Minutes from Cripple Creek/Victor and Woodland Park. Pet-friendly without additional fees for simply bringing your fur babies on your vacation. We do not charge a cleaning fee and only ask that dishes are washed and put away, and beds are stripped with dirty linens piled in the main living area, and closing instructions are followed.

20–27 Sep

$164 SGD per night

Guest favourite

Tiny home in Woodland Park

4.92 out of 5 average rating, 413 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 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 🤗

16–23 May

$146 SGD per night

Guest favourite

Cabin in Divide

4.92 out of 5 average rating, 357 reviews

Peak View Log Home

A log cabin/lodge/antique theme throughout the entire house. King log bed in the master, log queen and twin in upstairs bedroom. Wildlife and antler accents throughout. Do a search for “Visit Teller County” for TONS of vacation ideas!!!11 miles from Cripple Creek, 15 miles to Woodland Park and 30ish to Colorado Springs. Nearby hiking trails, gold medal fishing and ATV trails make this a wonderful vacation destination!

22–29 Jan

$243 SGD per night

Guest favourite

Cabin in Cascade-Chipita Park

4.97 out of 5 average rating, 206 reviews

Closer to the sun

This cabin is perfect for a couple or single mountain get away. The neighborhood is less than 10 minutes away from Manitou Springs and Woodland Park. The cabin has its own parking, private patio, and everything you need inside. There is a comfy queen size bed with a memory foam pillow top mattress, a fully equipped kitchen for cooking your favorite meals, as well as a spacious bathroom with stand in shower.

23–30 Oct

$154 SGD per night

Guest favourite

Cabin in Florissant

4.95 out of 5 average rating, 132 reviews

Red Door Cabin

While staying at Red Door Cabins you will enjoy breathtaking views, amazing rock formations, beautiful pine and aspen trees, a firepit, silence and stars. Have fun finding pieces of petrified wood, geodes, wild berries, and mushrooms on the property and surrounding area. You will get visited by deer, squirrels, maybe a family of foxes and occasionally local black bear or two. So, don’t forget your camera!

15–22 Mar

$162 SGD per night

Guest favourite

Cabin in Colorado Springs

4.97 out of 5 average rating, 235 reviews

Renovated Log Cabin in the Woods

Events are allowed with permission and for an additional fee. This 1-bed, 1-bath cabin is more than just a place to rest. It's a place to spend intentional quality time. It offers a retreat from the hustle and bustle of Colorado Springs yet is just minutes from grocery stores and restaurants. This historic cabin has over 100 years of history, but is well equipped with modern amenities for our guests.

8–15 Jan

$191 SGD per night