Family-friendly holiday rentals in Lake Gregory

4.95 out of 5 average rating, 128 reviews

MODERN MOUNTAIN CABIN IN THE TREES

Kick back and relax in this stylish cabin in the San Bernardino Mountains: minutes from downtown Crestline, Lake Gregory and Lake Arrowhead. Just 74 miles from downtown Los Angeles. window AC units installed May- Sept for summer cooling needs. Each of the two bedrooms features a King bed and cozy bedding. Fully Equipped updated kitchen includes a dishwasher, filtered water tap, and Nespresso. Samsung Frame TV with Hulu, Netflix. Gas Fireplace and plenty of games and records to enjoy your stay.

4.98 out of 5 average rating, 476 reviews

A comfortable seating area features a large leather chair and ottoman, positioned in front of a modern gas fireplace, which is glowing warmly. Floor-to-ceiling windows reveal scenic views of the outdoors, and subtle lighting from above creates a cozy ambiance.

Chalet in Crestline

Magical Mid-Century Cabin Epic Views & Fireplace

Nestled just a short distance from LA, embrace the idyllic landscape of picture-perfect sunsets from the balconies and awe-inspiring views from the house. Discover the orchestra of ravens and crows while savoring your morning coffee, or get lost in a book by the fireplace. Featured in Fodor’s Travel “Best Airbnbs and cabins of the year”! A 4-minute drive to Lake Gregory, 12 minutes to Lake Arrowhead, & 45 minutes to Big Bear. So much to explore or stay cozy inside, you will enjoy your time here.

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.

4.87 out of 5 average rating, 124 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

A spacious bedroom features a large bed with a dark patterned blanket, complemented by a decorative yellow cushion. Light streams through a window with angled wood beams accentuating the high ceiling. Two white side tables are positioned on either side of the bed.

4.97 out of 5 average rating, 214 reviews

Mountain Views | Hot Tub | Fire Pit | EV Charger

Welcome to this bright and airy, fully remodeled, meticulously maintained, modern, mountain cabin in the lakeside town of Crestline. Soak in the natural light from all angles with floor to ceiling windows that frame the beautiful mountain views from the comfort of the living room. Walk out onto the spacious front deck perched above the trees to sip your morning coffee. Enjoy any of the king size memory foam mattresses in every room. 5 min walk to Lake Gregory, 15 min drive to Lake Arrowhead.

4.99 out of 5 average rating, 147 reviews

A scenic view of the lake is framed by tall trees, capturing a soft sunset glow over the water. The landscape features a mix of greenery and distant hills, creating a tranquil atmosphere. The rooftops of nearby structures are visible in the foreground.

Home in Crestline

Spacious Lake View Mtn Home - Walk to Lake - Clean

Perfect mountain getaway - designed for comfort & gatherings. Spacious mountain home w/ lake views. Comfortable, stylish, & exceptionally clean. A blend of mid-century charm & rustic design. 5 bed / 3.5 bath, a primary suite & a media room. fireplaces & a 65" TV for cozy evenings. Kitchen opens to a breakfast bar & a large dining table that seats up to 10. Fully stocked w/ amenities & entertainment, bumper pool, darts, & board games. Two levels of patio space, propane BBQ, outdoor bar seating.

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, 180 reviews

Designer Cabin at LAKE Gregory- walk to town

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.

A spacious deck is framed by a wooden pergola, providing views of lush trees and a serene lake in the distance. Comfortable outdoor furniture is positioned for relaxation while enjoying the natural surroundings, with soft light suggesting early morning or late afternoon.

4.91 out of 5 average rating, 159 reviews

BEST VIEW Lakefront Cabin- Lake Gregory/Arrowhead

Welcome to the Sister's Lake House! This quaint 3 bedroom/2 bath, rustic lakefront cabin is the perfect weekend getaway with THE BEST VIEW of the LAKE! Guests will enjoy 180-degree PANORAMIC VIEWS of Lake Gregory. Lake Gregory is a four-season resort community that has activities for everyone! Our fully-stocked cabin is walking distance to the lake, grocery & restaurants, & a 15 min drive to Lake Arrowhead. Enjoy lake activities, hikes, fishing, BBQs, & star gazing off the patio. 8ppl & 3 cars

4.92 out of 5 average rating, 133 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

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, 280 reviews

Perfect Hideaway near the lake, Lots of 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, 155 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)

The cabin features a three-story structure with a red and white exterior, nestled among pine trees. Multiple decks are visible, with outdoor seating arrangements. Large windows allow for natural light, highlighting the inviting architectural design set against the lush greenery.

4.95 out of 5 average rating, 211 reviews

Forest View Cabin with Jacuzzi & Game Room

Three story cabin nestled in the mountain community of Crestline California. The cabin overlooks the town and has a restricted view of Lake Gregory through the towering pine trees. Relax around the fire pit on the large back deck or take in the stars from the jacuzzi after a day of hiking and exploring. The master bedroom has a gas fireplace and private deck with beautiful views. The large game room can be used as a fourth bedroom and includes a comfortable queen size murphy bed.