Holiday rentals in Castle Pines

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Top-rated holiday rentals in Castle Pines

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

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Guest favourite
An inviting outdoor space features a gas firepit surrounded by several seating options on a grassy area. A wooden deck leads to the house, with stairs ascending to the upper level. Scenic views of the open space and wildlife are visible in the background.
Home in Castle Rock
4.96 out of 5 average rating, 155 reviews

Large Luxurious Home Breathtaking Views w/ FirePit

Elevate your getaway experience at our exceptional Airbnb, where breathtaking views and modern amenities converge for the ultimate retreat. Situated just 5 minutes from downtown, our home offers the perfect blend of convenience and tranquility. Recharge your electric vehicle at our charging station and make the most of your stay with top-notch entertainment through our surround sound system. Book your stay today and discover a world where luxury, relaxation, and convenience harmoniously coexist.

Top guest favourite
A modern cabin is nestled among tall trees, showcasing a snow-covered landscape. Large windows provide views of the interior, where warm light glows from inside. A hot tub is visible on the deck, inviting relaxation amidst the serene winter setting.
Cabin in Black Hawk
4.99 out of 5 average rating, 512 reviews

Riverfront Cabin | Hot Tub, Fire Pit, Steam Shower

★★★★★ “The perfect blend of luxury and nature.” – Haley 💦 SPA BATHROOMS – Steam shower + jetted tub 🌿 HOT TUB & HAMMOCK – Soak creekside or sway in the trees 🔥 COZY EVENINGS – Fire pit, BBQ grill, fireplaces & in-floor heat ❄️ COOL COMFORT – Summer A/C 🐾 PET & FAMILY-FRIENDLY – Trails, Pack ’n Play, high chair 📶 FAST WI-FI – Stream, Zoom, or unplug 📍 10 min ⭆ Nederland — mtn town & adventure hub ➳ Breathe deep. Reconnect with what matters. ♡ Tap Save —unforgettable cabin stays start here

Top guest favourite
The cabin's exterior showcases rustic wood siding surrounded by lush trees and large boulders. A spacious deck equipped with string lights enhances the inviting ambiance. A picnic table and a gas grill are situated on the patio, offering a charming outdoor dining experience.
Cabin in Cascade-Chipita Park
4.99 out of 5 average rating, 256 reviews

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

Guest favourite
Home in Castle Rock
4.88 out of 5 average rating, 127 reviews

Spacious Cozy Walkout Basement.

Spacious and bright walkout basement with cozy bedroom, walk-in closet, small kitchenette, full bathroom, complete living room with queen sofa bed and large washer and dryer. Private entrance through the backyard with access to to the outdoor patio. Right in the heart of Castle Rock. 5 minutes from the Outlets, 45 min from the airport, 25 min from Denver. PLEASE NOTE - Our family lives upstairs including kids, some noise can be heard from below specially weekday mornings, evenings and weekends

Top guest favourite
Bungalow in Castle Rock
4.96 out of 5 average rating, 251 reviews

1920's Historic House Short Walk to Downtown

Enjoy all the modern conveniences & updates while experiencing the charm of a 1920's historical house. Enjoy time together in the open concept living room, dinning, and kitchen. Watch the sunset in the enclosed front porch, and sleep in comfort on one of the 3 beds in the house. You will have plenty to do being 2 blocks from downtown Castle Rock; close to trails, restaurants, parks, the outlet malls, zip-lines, and so much more. Close to Denver and Co Springs. This house will not disappoint!

Top guest favourite
The open living area is defined by exposed wooden beams and wide windows. A vintage trunk serves as a coffee table, complemented by a dining table and chairs. The kitchen features modern appliances, with a clear view of the stairs leading to the upper level.
Home in Castle Rock
4.98 out of 5 average rating, 495 reviews

Historic 1890s Barn | Spa Bath - Steps to Downtown

Experience a luxurious and fully restored 1890s barn on the first homestead property in the heart of downtown Castle Rock. High-end finishes throughout ensure your complete comfort and relaxation. Coffee, antiques, restaurants, shopping, and Festival Park are only a two minute walk from your front door. Enjoy a taste of simple, country living as you walk past our garden, chickens, and wild rabbits. The large, 1/2 acre property is charming, spacious, and the perfect backdrop for your stay.

Top guest favourite
A hot tub is foregrounded, reflecting the clear blue sky. In the background, a wooden deck is visible, shaded by an umbrella. Lush greenery surrounds the space, creating a relaxing outdoor environment.
Home in Castle Rock
4.99 out of 5 average rating, 224 reviews

THE ROCK HOUSE-HotTub,Crib,PoolTable,5Bedroom3Bath

Experience Colorado to its fullest. Easy access to I-25 to visit Denver & Colorado Springs, walking distance to downtown Castle Rock and the trailhead to hike The Rock. Amazing location near hiking, Castlewood Canyon, golf, parks & shopping. Enjoy views while in the hot tub, shoot a game of pool, watch a movie on the 70” TV, warm up by the fireplace or cook dinner in our fully stocked kitchen. This spacious house is renovated and ready to host your trip with friends and family! Crib included!

Top guest favourite
A private hot tub is situated on a patio, inviting relaxation. A barbecue grill is located nearby, alongside a hammock suspended between posts. Steps leading to the upper level are visible in the background, surrounded by landscaped areas and a wooden fence.
Guest suite in Castle Rock
4.98 out of 5 average rating, 189 reviews

Boho Basement - Private Entrance - Hot Tub

Welcome to Boho Basement - This charming one-bedroom walkout apartment is nestled in a prime location just minutes away from downtown Castle Rock, local parks, and hiking trails. Discover a warm and inviting space complete with a full kitchen, ample living space, and a luxurious king-size bed. A private hot tub awaits you outside, providing the perfect spot for unwinding. At Boho Basement, you can enjoy all the comforts of home while experiencing the beauty of Colorado. Book your stay today!

Top guest favourite
A modern kitchen features sleek white cabinetry and a spacious granite countertop. Full-sized stainless steel appliances include a refrigerator, oven, and microwave. Two place settings are set on the counter, enhancing the inviting cooking space, complemented by pendant lighting above.
Guest house in Castle Rock
5 out of 5 average rating, 286 reviews

Cozy and Comfortable Castle Rock Gem 2 Bedroom

Escape from the city to this cozy, private guesthouse. Our sleepy neighborhood sits high up on a ridge overlooking quaint Castle Rock. Minutes away is the historic town of Castle Rock with eclectic restaurants, boutique shopping, breweries, parks and the nearby outlet mall. Step out to gorgeous Colorado sunsets, mountain views, nearby walking trails and enjoy this peaceful setting. Perfect spot to call home while you explore all that Castle Rock, Denver and the Rocky Mountains have to offer.

Top guest favourite
Cabin in Cascade-Chipita Park
4.95 out of 5 average rating, 225 reviews

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!

Guest favourite
The living room features a comfortable sofa facing a flat-screen smart TV, complemented by a coffee table. Natural light enters through sliding glass doors, which lead to a small balcony. A small dining space with two stools is visible in the background.
Flat in Castle Rock
4.88 out of 5 average rating, 102 reviews

Rocky Mountain Haven w/ king bed | pool & hot tub

Unwind in the stylish one-bedroom apartment in Castle Rock, located in Castle Rock and a short drive from Pikes Peak. City is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through the city easily from this prime location. Once you are ready to relax, retreat to your comfy apartment. ✔ Fully Equipped Kitchen ✔ Comfy King bed and sleep sofa ✔ Dining Table ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool (Seasonal) ✔ Hot Tub Learn more below!

Top guest favourite
An outdoor seating area is enclosed by a wooden fence, featuring two chairs positioned on a patterned floor. Floral decorations adorn the fence, while potted flowers add a touch of color, creating a welcoming environment for relaxation.
Home in Castle Rock
4.94 out of 5 average rating, 156 reviews

Feels Like Home, Comfy & Cozy

Welcome to Comfy and Cozy**Private entry into our lower level of our ranch style house**Outside seating**Q-size bed w/plenty of space for your belongings**Living room/dining room, coffee, microwave, small fridge**Smart TV, WiFi**Private bathroom**No Cleaning Fees**We are located 1 mile from historic downtown, festival park, shopping & many restaurants. Just 3.5 miles to Philip Miller Park also known as the MAC, hiking and biking trails**Castle Rock has truly become a destination place**

Popular amenities for Castle Pines holiday rentals

  1. Airbnb
  2. United States
  3. Colorado
  4. Douglas County
  5. Castle Pines