Family-friendly holiday rentals in Crestline

4.9 out of 5 average rating, 118 reviews

Villa in Crestline

Crestline Villa for 8 Guests + Add-On Suite for 4

Escape to Crestline’s Lake Retreat, just 2 minutes from Lake Gregory! This serene two-story villa offers breathtaking mountain views and space for up to 12 guests. The main floor sleeps 8 with 3 bedrooms, 2 baths, laundry room and a spacious living room. Add the downstairs suite for an additional fee of $50 per night to sleep 4 more, featuring a private living/game room, bedroom, bathroom, and kitchenette. Ideal for families or groups, enjoy the relaxing backyard, game room, and stunning views!

A private hot tub is situated on the upper deck, surrounded by lush trees. The serene landscape includes a sunset sky with soft clouds, creating a tranquil atmosphere for relaxation.

4.95 out of 5 average rating, 307 reviews

GenevaChaletHOT TUB! WlkLakeGreg,Family&PetFrndly

The finest views in Crestline from Geneva Chalet. Newly modernized accommodation in private 2-level mountaintop cabin with picturesque tree-top views! Unwind in our hot tub on the deck amongst the trees! Our Family Friendly 2 bedroom, 2 bathroom Chalet comfortably sleeps 6 guests. Close to downtown Crestline, 1 mi. walk to Lake Gregory, hiking-trails, off-roading activities, water park, snow sledding/skiing and only 15 minutes from Lake Arrowhead. Come enjoy our family friendly cozy cabin!

Superhost

An outdoor hot tub is illuminated with purple lights, creating a serene atmosphere as twilight approaches. The surrounding deck is visible, with trees silhouetted against the fading light of dusk.

4.84 out of 5 average rating, 142 reviews

Hot Tub ~TESLA LVL2 Charger ~ Modern 2Br 2Bth ~ AC

🏠 Newly renovated home - Everything is new! ♨ Outdoor Hot Tub Spa! 🔌 Tesla Level 2 charger 🛏 King bed in the master bedroom 🛏 Two twins in the 2nd bedroom, one of them is a trundle bed. 🏞 Ample deck to enjoy the outdoors 🔥 Outdoor Firepit ⛵️ 3 minute drive to Lake Gregory ⚡️Lightning fast internet 📺 55” Roku TV in living room and 43” Roku TV in master Bedroom 🙋🏼‍♀️ Alexa connected Apple Music in living room and bedroom 🔥 Gas grill 🐶 Support animals require documentation + $100 fee

An inviting living space features large windows that provide expansive views of the mountains and sunset. A cozy seating arrangement includes a plush sofa and an accent chair. Natural light fills the room, with warm tones from wooden beams and decor creating a relaxing atmosphere.

4.99 out of 5 average rating, 142 reviews

Mid-Century A-Frame Retreat w/ Mountain Views

The Oso A-Frame cabin has been fully remodeled to provide a serene mountain experience. A quick 5-minute drive to Lake Gregory, the cabin sits perched on a hillside, allowing private, expansive views of the sunset. Brand new bathrooms, cozy central heat, AC, fully stocked kitchen, & pet friendly, we invite you to enjoy time with family and friends. Remote workers welcomed with ultra-fast wifi. If you are looking for a quiet retreat to recharge, this is the place for you! CESTRP-2022-01285

The outdoor patio features a rustic fire pit surrounded by several Adirondack chairs, inviting relaxation. A wooden deck leads to the entrance of the cabin, set against lush greenery and shade provided by tall trees. The cabin's stone chimney adds character to the setting.

4.95 out of 5 average rating, 221 reviews

Designer Cabin at LAKE Gregory- walk to shops!

A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

4.98 out of 5 average rating, 495 reviews

Chalet in Crestline

Magical Mid-Century Cabin | Epic Views & Vinyl

Welcome to The Magical Cabin, a peaceful, mid-century retreat nestled among the pines in Crestline. Embrace the idyllic mountain landscape, with awe inspiring views throughout the cabin and picture perfect sunsets from the decks. An inviting & inspiring escape for couples, solo travelers & creative souls looking to reconnect & recharge. • 5 min to Lake Gregory, town & grocery store • Record player + vinyls • Featured in Fodor’s Travel “Best Airbnb's & Cabins of the Year” • Cozy gas fireplace

4.99 out of 5 average rating, 270 reviews

Guest suite in Crestline

100-Mile View | Romantic Chalet • Dogs Welcome

Holly Hill Chalet is designed for romantic interludes and peaceful retreats. While the interior is stylish and cozy, the true star of the show is the view: an ever-changing masterpiece that transitions from golden sunrises to cinematic sunsets. From our expansive patios and park-like garden, you have a front-row seat to the awe-inspiring expanse below. As twilight descends, the horizon dissolves into a sea of twinkling city lights, igniting a garden of whimsical light, chandeliers, and magic.✨

4.92 out of 5 average rating, 152 reviews

Breathtaking Lakefront Home

My husband and I are nature enthusiasts who love the mountains and the lake. We fell in love with this beautiful place the moment we arrived. Dalat Homestay was truly love at first sight. Designed to feel simple and cozy like home, it’s where our family comes to relax, unwind, and reconnect with nature. Perfect for a family vacation, romantic getaway, or quiet escape from the city. Everything is close by: • 1-mile walk to the lake • Local café & grocery – 1.5 miles • Lake Arrowhead – 8 miles

4.88 out of 5 average rating, 387 reviews

A+ Alpine A-Frame | Hot Tub+Views | 95 Min from LA

95 mins from Los Angeles, this is the weekend reset you come to the mountains for - morning coffee on the deck above the trees, wildflower excursions on the trails, and nights in the hot tub under a starry sky. Our Cabin in the Sky is a 1960s A-frame for groups/couples who want a quiet, extraordinary cabin experience . Separate 1 bdrm apt avail for extra fee for guests of main house. Perfect for in-laws, teens or groups who need extra space: separate kitchen, queen bedroom & full bathroom.

A welcoming cabin is nestled among tall pine trees, showcasing a blend of natural wood and a charming brick exterior. A front deck with a simple railing invites relaxation, while a California flag hangs nearby, enhancing the rustic feel of this peaceful retreat.

4.93 out of 5 average rating, 294 reviews

Perfect Hideaway near the lake, flat parking

Nestled on the best street in Crestline, our sweet cabin is a perfect hideaway! Our property is surrounded by pine trees and makes you feel like you are separated from the world! Only a 15 minute beautiful walk to the lake but you may not want to leave the hideaway! We have everything you need to stay in or adventure out! Feed the birds with your morning coffee on our deck, grab a flashlight for an evening stroll or play games by the fireplace. Plenty of flat land for play n parking!

A spacious wooden deck features multiple black outdoor chairs arranged around a circular firepit. The setting sun casts a warm glow, with trees visible in the background, enhancing the serene atmosphere of the space.

4.95 out of 5 average rating, 182 reviews

Cozy Cabin | Large Deck & Firepit Near Attractions

✨ Why You’ll Love It: 🔥 Wood-burning fireplace for cozy nights ☕ Large deck for morning coffee & sunset views 🛋 Stylish, open-concept living space with natural light 📍 Perfect Location: 🏞 1 mile – Lake Gregory (boating, fishing, swimming) 🍽 1 mile – Crestline’s best dining & shopping 🥾 10 mins – Heart Rock Trail (scenic waterfall hike) 🌲 15 mins – Sky Forest (charming alpine village) 🚤 20 mins – Lake Arrowhead (shopping & boat tours) ⛷ 35 mins – Snow Valley (skiing & snowboarding)

An expansive deck features a circular gas fire pit surrounded by four lounge chairs. String lights are hung above, creating a soft glow. Tall trees are visible in the background, enhancing the outdoor setting.