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Family-friendly vacation rentals in Lake Gregory

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Lake Gregory

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

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Cabin in Crestline

4.91 out of 5 average rating, 135 reviews

BEST VIEW Lakefront Cabin- Lake Gregory/Arrowhead

Welcome to the Sister's Lake House! This quaint three 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 cabin is walking distance to the lake, grocery store & restaurants, & a short 15 min drive to Lake Arrowhead. We follow Airbnb’s enhanced cleaning protocols for our guests’ safety. 8ppl max /3 cars

Aug 5 – 12

G$65,442 GYD per night

Cabin in Rimforest

4.96 out of 5 average rating, 391 reviews

Fort Black Bear w/ Hot Tub - Lake Arrowhead

Our chic mountain retreat is everything you'd want in your Lake Arrowhead getaway. Beautiful wood cathedral ceilings accent the views of trees, boulders and peeks of the city lights far below. The expansive great room is anchored by a stone fireplace, wrap around sectional and large inviting dining area. A fully outfitted cook's kitchen, roman tub with picture window, king size bed and large dining table make this the ultimate retreat. Enjoy the cedar clad hot tub set next to massive boulders!

Jul 22 – 29

G$50,442 GYD per night

Cabin in Crestline

4.87 out of 5 average rating, 238 reviews

Cozy Cabin in Crestline/Lake Gregory

Cozy Mountain Cabin located in the sleepy town of Crestline. Lake Gregory is a 5 min drive. Close to all shops and activities. Nicely decorated mountain retreat sure to please most families. The cabin has a gas fireplace, entertainment options, and a backyard with a fire pit and bbq grill. The town of Crestline and Lake Gregory has many shops, restaurants and a bowling alley nearby. Lake Arrowhead is 20 mins away. Big Bear and other resorts are about 40 min drive. SORRY BUT NO PETS ALLOWED.

Jul 12 – 19

G$23,626 GYD per night

Cabin in Crestline

4.93 out of 5 average rating, 165 reviews

Cresta Moon Cabin

Welcome to Cresta Moon Cabin- a great place to bring the family, get away for a romantic weekend or just spend time with friends. Rustic Miners Cabin, 2 Large bedrooms with plenty of space. Relax on the treetop deck and watch the squirrels and blue jays play. Beautiful Dogwood and Pine Trees to enjoy. Fenced back yard. Short drive to Lake Gregory, 15 min to Lake Arrowhead or Santa's Village, 30 min to Snow Valley for Skiing and Snowboarding. Hiking, Fishing, Shopping, Hang Gliding - lots to do.

Jun 22 – 29

G$25,110 GYD per night

Cabin in Lake Arrowhead

4.92 out of 5 average rating, 125 reviews

Lake Arrowhead Forested Modern A-Frame Cabin

Close to restaurants, family-friendly activities, quiet neighborhood and great outdoor space, good for couples, solo adventurers, business travelers, families (with kids), big groups. Master suite with king size bed and its own bathroom. Two bedrooms with queen size beds, (one of these has a twin bunk) and hall bath, a basement with full size bunk beds, convertible couch, bath and laundry, kitchen/living room with two story views, fully furnished, cable TV and high speed internet, EV charging.

May 10 – 17

G$33,390 GYD per night

Cabin in Twin Peaks

4.97 out of 5 average rating, 274 reviews

A/C, Jacuzzi, Huge Fenced Back Yard, Dog Friendly

~ Rustic 750 Sq. Ft cabin. Dog Friendly, fully fenced, beautiful lighting throughout. 8 min to Lake Arrowhead & Lake Gregory ~ Attending a Wedding at the Pine Rose? We are next door! ~ Walking distance to a small market and the best restaurant on the mountain (The Antler Grill) ~ Romantic wood burning fireplace. Central heat & A/C, 65" TV, cable & internet ~ Backyard gas BBQ , 3 person Jacuzzi (2 seat, 1 lounge) hammock, horseshoes & outdoor shower (Indoor as well) ~ Easy parking

Sep 18 – 25

G$39,917 GYD per night

Cabin in Green Valley Lake

4.84 out of 5 average rating, 279 reviews

Little House on the Forest

Come on up to Green Valley Lake! The lake is stocked with rainbow trout and bass, the weather is cool and we're surrounded by national forest full of beautiful hiking trails. Fun for all ages with a beach for the kids and a giant swan and yellow duck paddles boats to paddle around the lake (nominal fees). Bring your bicycles or go off-roading. Completely upgraded cabin in natural setting close to private lake, village and restaurant. You'll have so much fun you'll never want to go home!

Jul 14 – 21

G$17,564 GYD per night

Guest suite in Crestline

4.84 out of 5 average rating, 226 reviews

1st Floor - 1 mile from San Moritz Lodge

Lake Gregory is known as the Swiss Alps of the West. Our Swiss chalet is a real mountain get away for you and your family! The remodeled cabin is a duplex among tower trees in a beautiful nature setting. Situated between 2 creeks, that are know to be a part of a wildlife trail. Our home is a mile from the lake and San Moritz Lodge. Our place is ideal for those enjoying weddings and events at the lodge, hiking and enjoying lake activities. We are 18 miles from skiing and snowboarding.

Sep 11 – 18

G$24,777 GYD per night

Chalet in Crestline

4.86 out of 5 average rating, 178 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.

Jul 19 – 26

G$23,488 GYD per night

Cabin in Crestline

4.83 out of 5 average rating, 215 reviews

Vintage Cabin in the Woods

30's built cabin with all the charm and amenities you’d want. If you're looking for a getaway from the city you can expect to be half an hour away from big bear and closer to everything else. This property is 1 mile away from everything the town of Crestline has to offer; shopping, fast food, bars, park/lake, fishing, overall fresh air and more. The property is left to you to enjoy and explore. All thats expected is to be left clean.

Jun 15 – 22

G$34,093 GYD per night

Cabin in Running Springs

4.98 out of 5 average rating, 260 reviews

Glen Oak Rim | Hot Tub · Game Room · Epic Views

Couples, Families, & Mountain Peace Seekers only, please. Located at the base of a steep private drive and overlooking the San Bernardino Basin sits this stunning California family cabin. Originally constructed in 1965, the dwelling's Mid-Century details have been lovingly restored while not forgetting a single modern amenity. Brilliantly designed by SoCalSTR® | IG: @socalstr "Top 1%" local market performer according to AirDNA

Sep 1 – 8

G$47,707 GYD per night

Cabin in Rimforest

4.91 out of 5 average rating, 552 reviews

1930 Cozy One Bedroom Lake Arrowhead Cabin

Rustic & romantic, our cozy cabin has vaulted ceilings, original paneling, a wood-burning fireplace, and a fully outfitted kitchen. The backyard is the National Forest. The front deck is a lovely location for morning coffee or an evening glass of wine. WiFi (Download = 114.2 Mbps, Upload = 11.3 Mbps), Smart TV, Alexa, music player (vinyl, CD, cassette, and Bluetooth), DVDs, VHS, games, books, heating & air conditioning.

Mar 20 – 27

G$16,449 GYD per night

Vacation rentals for every style

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Cabins

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Stylish accommodations and amenities

Popular amenities for Lake Gregory family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cabin in San Bernardino County

4.96 out of 5 average rating, 145 reviews

Cozy lil Cabin w/Hot Tub&Fireplace! Walk to shops!

Oct 23 – 30

G$38,917 GYD per night

Cabin in Lake Arrowhead

4.98 out of 5 average rating, 135 reviews

Mountain Cabin w/ Gameroom, Great Views & Spa

Nov 27 – Dec 4

G$137,201 GYD per night

Cabin in Twin Peaks

4.97 out of 5 average rating, 317 reviews

Real Log Cabin Built in 1915 with Modern Comforts!

Sep 5 – 12

G$76,892 GYD per night

Cabin in Lake Arrowhead

4.94 out of 5 average rating, 317 reviews

Lake view with hot tub, EV charger

Feb 3 – 10

G$79,854 GYD per night

Cabin in Lake Arrowhead

4.94 out of 5 average rating, 309 reviews

A-Frame Lodge Cabin with Hot Tub and Fire Pit

May 25 – Jun 1

G$51,607 GYD per night

Home in Lake Arrowhead

4.94 out of 5 average rating, 245 reviews

Exquisite Mountain Home Near Lake and Village

Apr 10 – 17

G$53,854 GYD per night

Cabin in Big Bear Lake

4.95 out of 5 average rating, 832 reviews

Wine Down Cabin - great LOCATION + SPA + PET ok

May 9 – 16

G$29,325 GYD per night

Cabin in Lake Arrowhead

4.87 out of 5 average rating, 279 reviews

Vintage Modern A-frame

Aug 16 – 23

G$73,851 GYD per night

Family- and pet-friendly home rentals

Cabin in Tyrol Court Crestline

4.83 out of 5 average rating, 184 reviews

Walk2Lake-Beautiful Cozy Getaway/Retreat for ALL!

Sep 17 – 24

G$53,984 GYD per night

Cabin in Lake Arrowhead

4.79 out of 5 average rating, 194 reviews

Magic Love Nest - 5 min from village, stream below

Oct 22 – 29

G$25,351 GYD per night

Cabin in Running Springs

4.87 out of 5 average rating, 261 reviews

Mountain Cottage

Jul 21 – 28

G$20,817 GYD per night

Cabin in Running Springs

4.86 out of 5 average rating, 724 reviews

A-Frame Of Mind: private + epic views

Oct 9 – 16

G$37,747 GYD per night

Cabin in Lake Arrowhead

4.98 out of 5 average rating, 130 reviews

The Lazy Bear Lodge

Sep 22 – 29

G$30,628 GYD per night

Cabin in Lake Arrowhead

4.96 out of 5 average rating, 312 reviews

🌿 A Peaceful Getaway in Lake Arrowhead! 🌿

May 16 – 23

G$33,785 GYD per night

Home in Lake Arrowhead

4.96 out of 5 average rating, 113 reviews

New Home 2 Mstrs, AC, EV Chgr, eBikes, Lake Rights

Sep 22 – 29

G$141,184 GYD per night

Home in Lake Arrowhead

4.86 out of 5 average rating, 175 reviews

Modern retreat with amazing lake view!

Apr 23 – 30

G$134,965 GYD per night

Family-friendly home rentals with a pool

Guesthouse in Redlands

4.99 out of 5 average rating, 278 reviews

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Dec 8 – 15

G$23,141 GYD per night

Cabin in Hesperia

4.93 out of 5 average rating, 144 reviews

Little Horsethief Hideaway at Silverwood Lake

Sep 24 – Oct 1

G$79,624 GYD per night

Cabin in Big Bear

4.86 out of 5 average rating, 489 reviews

The Sugar Shack with Hot Tub, Mountain Serenity

Aug 12 – 19

G$15,349 GYD per night

Home in Morongo Valley

4.81 out of 5 average rating, 247 reviews

Morongo Star Ranch - Rolling Hills w/ Pool & Spa

Oct 20 – 27

G$64,540 GYD per night

Bungalow in Pioneertown

4.93 out of 5 average rating, 363 reviews

ZenDen - the perfect couples desert getaway

Nov 20 – 27

G$66,517 GYD per night

Home in Fontana

4.96 out of 5 average rating, 180 reviews

❤️Large & COZY , 6 Bedrooms With 65” Tvs + Pool ❤️

Jul 8 – 15

G$135,701 GYD per night

Condo in Big Bear Lake

4.83 out of 5 average rating, 201 reviews

Beautiful Condo near Village, Slopes, Lake.

May 20 – 27

G$35,115 GYD per night

Condo in Big Bear Lake

4.86 out of 5 average rating, 324 reviews

Lakeside Condo 2B/2B - Walk to Lake, w/ Jacuzzi!

May 8 – 15

G$25,263 GYD per night

Destinations to explore