Vacation rentals in Lake Gregory

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Top-rated vacation rentals in Lake Gregory

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Guest favorite

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.

Cabin in Crestline

4.88 out of 5 average rating, 112 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

Guest favorite

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

4.98 out of 5 average rating, 452 reviews

Magical Mid-Century Chalet Breathtaking Views!

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 an 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 Airbnb’s 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!

Top guest favorite

The exterior of the cabin features a welcoming front porch with a swing and a wooden beam structure. Framed by tall trees, the white facade and large windows complement the natural surroundings, creating a serene entryway for guests.

Cabin in Twin Peaks

4.99 out of 5 average rating, 290 reviews

The Acorn Cottage

Escape to the mountains and cozy up at The Acorn Cottage, a tiny oasis located near beautiful Lake Arrowhead. Featuring breakfast seating, living room for watching TV or playing games, one full-bath, a roomy bedroom upstairs, a gas fire pit and bbq on the deck with comfy seating and dining. This is the perfect little getaway! Sit outside in the morning with your cup of coffee on our beautiful patio and sit by the fireplace at night with a glass of wine or cup of tea after your daily activities.

Guest favorite

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.

Cabin in Crestline

4.95 out of 5 average rating, 134 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.

Guest favorite

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.

Cabin in Crestline

4.91 out of 5 average rating, 154 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

Guest favorite

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.

Cabin in Crestline

4.98 out of 5 average rating, 119 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, ice cold AC ❄️and fully stocked kitchen 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! Find us on IG @osoaframe CESTRP-2022-01285

Top guest favorite

A person sits at a table with a small vase of flowers, enjoying a scenic view of rolling green mountains and a clear blue sky. The lush landscape extends into the distance, with varying shades of green and hills melting into the horizon.

Guest suite in Crestline

4.99 out of 5 average rating, 240 reviews

Breathtaking Mountain Views | Romantic Hideaway

Holly Hill Chalet is ideal for romantic interludes or peaceful retreats, we promise an unforgettable experience. Expansive patios and park-like setting for garden. The true star of the show is the view an ever-changing masterpiece that transitions from incredible sunrises to beautiful sunsets, all the while offering a front-row seat to the awe-inspiring expanse below. As twilight descends, the view transforms into a sea of twinkling city lights, igniting the atmosphere with a touch of magic

Guest favorite

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.

Cabin in Crestline

4.96 out of 5 average rating, 250 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!

Guest favorite

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.

Cabin in Crestline

4.96 out of 5 average rating, 134 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)

Guest favorite

An open-concept living space features a cozy blue couch and a wooden coffee table. Large glass doors lead to a deck, while a stone fireplace creates a central focal point. Light oak flooring and wooden walls enhance the cabin's rustic charm.

Chalet in Crestline

4.85 out of 5 average rating, 218 reviews

Private cabin w wraparound deck at Lake Gregory

Our bright and spacious chalet nestled in the San Bernardino National Forest offers peace and seclusion within a mile from Crestline Village and Lake Gregory. 15 minutes from Lake Arrowhead and Santa's Village, 20 min from Snow Summit, 40 min from Big Bear, and walking distance to Lake Gregory Water Park in spring and summer! Crestline offers amazing thrifting and antiquing, biking, hiking, boating, fishing, or just take in nature at its best from the comfort of this cozy retreat.

Guest favorite

A spacious terrace extends alongside the home, offering unobstructed views of the lake and surrounding hills at sunset. Subtle lighting illuminates the area, while a pair of outdoor chairs provides a cozy spot to enjoy the serene backdrop.

Home in Crestline

4.97 out of 5 average rating, 203 reviews

Magical lake house with spectacular views

Gorgeous, tranquil retreat with enriching views of the lake and nature. A storybook bridge with the soothing flow of the stream beside it sets the mood for relaxation, inspiration and/or romance immediately. The home opens to captivating views of the entire lake from the curated, open floor plan. Ideal for cooking, quality dining, working on something creative or simply a peaceful escape from the city. Multiple terraces and balconies to enjoy the crisp air and setting.

Superhost

A spacious outdoor balcony is highlighted, featuring a hanging chair and a wooden table surrounded by comfortable seating. Scattered potted plants add a touch of greenery, while views of the serene lake and surrounding forest can be seen in the background.

Cabin in Crestline

4.91 out of 5 average rating, 114 reviews

Breathtaking Lakefront Home

Enjoy a beautiful lake view in one of the best locations at Lake Gregory. This charming cabin is the perfect retreat for the entire family, just minutes from Lake Arrowhead. Our cozy home features a fully equipped kitchen, plush blankets, comfortable beds, and all the amenities you need for a relaxing, stress-free getaway. Ideal for family vacation, getaway. Few minutes away from these locations: Local Cafe, grocery: 2 miles Lake Arrowhead: 8 miles Big Bear: 30 miles