Family-friendly holiday rentals in Bailey

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Top-rated family-friendly rentals in Bailey

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
Guest suite in Breckenridge
4.91 out of 5 average rating, 106 reviews

Breckenridge Wildlife Retreat/hot tub/dog friendly

Come ski Breckenridge! 5 minutes from down town & free skier parking for Breckenridge ski resort! Cute studio-like space in a house on 2 acres with incredible Rocky Mountain views from hot tub. Shared access to decks, hot tub & outdoor grill. Please look at pictures for details of space. Private bedroom & bathroom, double bed, sitting area, and hallway wet bar. Private parking and access. Enjoy 100+ restaurants & bars, dog sledding, snow mobiling, snow shoeing, x country. DOGS STAY FREE.

Top guest favourite
Cabin in Grant
5 out of 5 average rating, 123 reviews

Hygge Chalet & Sauna w/ Private Trail + EV Charger

Recharge at the Hygge Chalet & Sauna on 3.5 wooded acres with incredible views of the Rocky Mountains. The eco-friendly A-frame is inspired by hygge, a Danish sense of coziness & simple pleasures. An outdoor Finnish sauna, Level 2 EV charger, large wraparound deck, amazing views, luxury beds, & Norwegian fireplace create a perfect cozy vibe. Explore a private hiking trail that goes from our property for miles into National Forest. Relax, unplug, & reconnect in this uniquely curated experience.

Top guest favourite
A warm, rustic cabin interior is showcased with wood-paneled walls and vaulted ceilings. Large windows line the space, offering views of the surrounding trees. A comfortable seating area is arranged around a coffee table, and a stylish kitchen island features a visually appealing countertop.
Cabin in Bailey
4.97 out of 5 average rating, 115 reviews

Serene, Family Friendly Mountain Retreat

This beautiful, cozy, and sophisticated cabin is perfect for those who want to escape the everyday grind and immerse themselves in the natural beauty of the Rocky Mountains. Our cabin is packed with love and personality, featuring rustic decor, modern furnishings and all the comforts you need for a truly memorable stay. Soak in the surrounding mountains, forests, and wildlife from the spacious deck or cozy up to the fireplaces with a good book or loved one. Suitable for the whole family

Top guest favourite
The living room contains two dark leather sofas adorned with decorative pillows, positioned around a rustic coffee table. A potted plant adds a touch of greenery. Natural light filters in through a window, complementing the warm wood paneling on the walls.
Flat in Pine
4.86 out of 5 average rating, 145 reviews

Private mountain suite.... PERFECT LOCATION

Welcome to our private mountain retreat. You have access to the entire suite, with a key code. This unit is beautifully decorated. Updated to make your stay in the mountains amazing. Entire lower level, 2 bedrooms, kitchen, bathroom (note there is no bathtub, only a shower), laundry room with washer and dryer, board and iron, plus a large living room. Due to the location and lack of transportation options, some type of vehicle is required and 4 wheel drive is recommended in the winter.

Top guest favourite
A bright living area features large windows framing mountain views. A dark wood dining table with seating for four is positioned next to a comfortable red sofa. The room has wooden flooring and a warm wood ceiling, creating an inviting space with a television nearby.
Guest suite in Littleton
4.97 out of 5 average rating, 539 reviews

Mountain Chalet - Panoramic Views 45 Min to Denver

Serenity at 8,000 feet with Pine and Aspen trees. Address is Littleton, but it's part of the Conifer mountain community. The Chalet is a private quarters above our garage with a separate deck and entrance. We also host elopements and micro-weddings! Overlook mountains to the west and the Denver to the east. Hot tub is on the back deck of main house and overlooks city lights! Groceries, dining and hiking trails only 15 minutes away. There is no A/C. 4WD vehicles are required October - April.

Top guest favourite
The cabin's exterior is surrounded by tall pine trees, showcasing a warm wooden facade and a welcoming porch. Soft interior lights illuminate the entrance, highlighting the inviting architecture against the twilight sky.
Cabin in Jefferson
4.93 out of 5 average rating, 194 reviews

Modern Comfort, Incredible Views, & Local Nature!

This private remote cabin is quiet & situated on 6 acres among pine & aspens, and is just steps from Ntl forest & a only short walk to fishing and hiking. The cabin is warm & nicely furnished & comfortable & clean & everything is modern and updated (wifi is 100Mb+). The patio and deck are wonderful for relaxing & watching the wildlife & sunsets. This cabin is perfect for all seasons: Summer for the outdoors and sunsets, Fall for leaves changing, Spring for green views, Winter for cozy days.

Top guest favourite
A stunning treehouse structure is elevated on stilts, surrounded by lush greenery. Floor-to-ceiling windows offer expansive views of the mountains and valleys. The warm glow from outdoor lights adds ambiance at dusk, highlighting the inviting terraces and scenic backdrop.
Treehouse in Bailey
4.99 out of 5 average rating, 167 reviews

Luxury Treehouse + Glamping Tent - Views for Miles

Looking for a relaxing getaway that's out of this world? Come stay at the Zen Treehouse+ Glamping Tent, a breathtaking sanctuary nestled high up in the treetops overlooking beautiful Deer Creek Valley. A unique blend of luxury, nature, and tranquility with stunning panoramic views, lush greenery, and modern amenities, your stress will leave as soon as you arrive. Your stay at Zen Treehouse will rejuvenate your mind, body and spirit. Sleeps up to eight and only an hour from Denver.

Top guest favourite
A cozy living area features a large vegan leather couch accompanied by a warm throw blanket. Natural light filters through a window, highlighting the mountains outside. A wooden coffee table sits in front of the couch, creating a welcoming space for relaxation.
Home in Bailey
4.99 out of 5 average rating, 136 reviews

Cozy mtn escape with sweeping views + jetted tub

Welcome to Aspen Glow Cabin, our little slice of heaven nestled into the hillside in beautiful Bailey, Colorado. Our two bedroom cabin is the perfect place to unwind and relax from the craziness of city life or as a homebase to explore all of Colorado's bounties. With our decades of hospitality and design experience we have created a cozy space that predicts your every need and allows you to focus on enjoying your time here to the fullest. Come be our guest!

Top guest favourite
A spacious living room features a stone fireplace surrounded by large windows showcasing mountain views. Comfortable seating is provided by a light green sofa and a tan couch, while a decorative rug adds warmth. A wooden door leads to an outdoor area with additional scenery.
Guest suite in Evergreen
4.97 out of 5 average rating, 268 reviews

Come smell the pines from your exclusive suite!!

Jaw-dropping mountain views at 8600' high! That is what you will experience in this paradise from your exclusive suite. Enjoy, relax and chill on these 3+ acres overlooking the Rockies. Breathtaking place to sip an adult beverage, escape the city and recharge. Your suite includes a bedroom, bath, separate sitting/ dinning room and private entrance. Wildlife abounds from your window or go hiking and explore on your own. We look forward to meeting you!

Top guest favourite
A landscaped area features natural stone steps leading up a gentle incline. Surrounding elements include a mix of rocks, gravel, and blooming lavender, while tall pine trees provide a serene backdrop to the peaceful outdoor space.
Tiny home in Pine
5 out of 5 average rating, 224 reviews

Mountain Carriage House-(Tiny House)

This is a space of 360 sq. ft., which includes a small kitchenette, with microwave oven, toaster, coffee maker, hot tea kettle, and mini fridge. There is one full bathroom; please note that the bedroom and common area, which holds one sofa big enough for two people, is a shared space. This is a tiny house. Quaint and comfortable, and small. Enjoy fresh clean linens, and on cool days, bump the little red gas stove up and enjoy a cozy fire.

Top guest favourite
The cozy A-frame cabin is nestled among tall pine trees, showcasing a spacious front deck that offers outdoor seating. Sunlight filters through the trees, casting soft shadows on the surrounding grass. A cedar hot tub is visible on the deck, enhancing the cabin's inviting atmosphere.
Cabin in Bailey
4.99 out of 5 average rating, 344 reviews

Renovated 60s A-Frame | Cedar Hot Tub | Stargazing

Welcome to Front Range A-Frame, a cozy cabin getaway in Bailey, Colorado! Our renovated cabin offers retro charm with modern upgrades. Located just 60 minutes from downtown Denver, Front Range A-Frame is perfect for romantic getaways, quick escapes from city life, and Colorado vacation experiences. Relax on the front deck under the pines while the deer roam past you, or soak in the cedar hot tub under the night stars.

Guest favourite
A rustic cabin with a wooden exterior features a green roof and large front porch. An umbrella provides shade over outdoor seating. The surrounding landscape includes pine trees and mountain views, with peaks visible in the background under a partly cloudy sky.
Cabin in Bailey
4.86 out of 5 average rating, 332 reviews

420 Okay Colorado: Mt. Rosalie Cabin

The Cabin on Hall Rd is in Harris Park Estates in the rural outskirt of Bailey, Colorado. We are 50 mins southwest of Denver off of Highway 285. There are 2 bedrooms with a queen bed in one room & two single beds in the other room. The bathroom has a shower/tub. The kitchen is fully equipped. There is deck facing west with a view of Mount Rosalie, Mount Bierstadt, and Mount Evans. We are pet friendly and 420 friendly.

Popular amenities for Bailey family-friendly rentals

When is the best time to visit Bailey?

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Avg. price$270 SGD$264 SGD$268 SGD$256 SGD$297 SGD$320 SGD$340 SGD$323 SGD$318 SGD$290 SGD$276 SGD$310 SGD
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Quick stats about holiday rentals that are family-friendly in Bailey

  • Total holiday rentals

    Explore 150 holiday rentals in Bailey

  • Nightly prices starting at

    Bailey holiday rentals start at $131 SGD per night before taxes and fees

  • Verified guest reviews

    Over 11,750 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 90 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wifi availability

    150 of Bailey holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Bailey rentals

  • 4.9 Average rating

    Bailey stays are highly rated by guests – averaging 4.9 out of 5!

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