Holiday rentals in Lake Gregory

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!

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!

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

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.

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

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+ 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.

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)

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!

San Moritz Lake House | Walk to Lake Gregory | 3BR

Newly renovated 2024 3-bedroom, 2-bath Crestline mountain cabin sleeps 8 with fireplace, BBQ, Mrs. Pacman, two full levels of living space and two decks with peekaboo Lake Gregory views. Two full kitchens, stainless steel appliances, large island and central AC. Queen beds in two rooms, queen plus bunk bed downstairs. Lake Gregory directly across the street for swimming, kayaking and fishing. Minutes from Crestline Village and Snow Valley skiing.

Fairy Forest Cabin - Walk to Lake, Dog-Friendly

Escape to our charming Crestline cabin, a secluded mountain retreat just a 10-minute walk to Lake Gregory and town. Enjoy an expansive deck, fenced dog-friendly yard, and cozy fire pit. Inside, whimsical forest-inspired bedrooms bring the outdoors in. Near Crestline shops and dining, with Lake Gregory boating, fishing, and swimming nearby, plus easy access to hiking trails, Big Bear ski resorts, and year-round San Bernardino mountain adventures.

The Birdhouse | Designer Cabin by Lake Gregory

Welcome to The Birdhouse—a thoughtfully designed mountain retreat just a short walk from Lake Gregory. Built over 100 years ago, this one-of-a-kind cabin blends original character with modern comforts. Spend your mornings with coffee on the deck, afternoons exploring the lake or nearby trails, and evenings by the vintage 1960s fireplace or around the outdoor fire pit beneath the pines. Dogs are welcome! (Up to 2 dogs; $50 pet fee.)