Family-friendly vacation rentals in Gypsum

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Top-rated family-friendly rentals in Gypsum

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

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Guest favourite

Guest suite in Eagle

4.95 out of 5 average rating, 303 reviews

Mountain home paradise quiet home just above Eagle

Amazing spot, 1 mile N of I70 but worlds away. Great view from the deck, nice private location. We are a very active outdoor couple that are more than happy to share local info, help plan... we do just about every outdoor sport there is, and are happy to give any beta we can. We also have river toys (a raft, 2 paddleboards, a duckie/ inflatable kayak, and 3 hardshell kayaks) that can be Borrowed in exchange for wine ;). (You’ll need a vehicle with a rack or a truck to shuttle) Kaleb & Abby

Oct. 16 – 23

$158 CAD per night

Guest favourite

Cabin in Marble

4.98 out of 5 average rating, 164 reviews

Eco-Chic Off-Grid Cabin - Great Views and Design

It's doubtful you will ever stay in such a stunning place. Newly built, eco-chic, off-grid luxury cabin in the Crystal River Valley. Large sun deck. Separate master suite. 5 minutes from Marble, yet secluded. Beautiful natural hot springs nearby. Massive views in all directions. Soak it all in. This is a paradise for writers, poets, creatives, and lovers. Leave your cell phone at home on this trip. Landline and satellite wifi available to keep you connected. Welcome to your home away from home.

Oct. 17 – 24

$589 CAD per night

Superhost

Cabin in Carbondale

4.82 out of 5 average rating, 537 reviews

3Br 2 Bth + Skatepark at Ten Peaks Ranch nr Aspen

My place is close to great skiing in Aspen, beautiful hiking next door in White River National Forest, and great night life close by in Aspen and Carbondale. You’ll love my place because of The views in every direction. You can enjoy the dark valley and vivid sky at night, or be in the action in Aspen a short drive away. My place is good for couples, business travellers, families, big groups, and furry friends. Concrete skatepark and trampoline in the front yard for the daredevils among us.

May 27 – Jun. 3

$537 CAD per night

Guest favourite

Guest suite in Silverthorne

4.97 out of 5 average rating, 965 reviews

Bighorn Lodge- Sputnik Suite

Minutes from Keystone, Breckenridge, Loveland, Arapahoe Basin and Copper Mountain ski resorts, this suite is a skiers paradise. Our luxe designer guest suite sleeps 2 with a king bed and has a private, attached bathroom. Better quality than any local hotel, a fraction of the price! West & north facing windows with huge mountain vista views of the Gore range. The main entrance is shared, with the private access to your studio located just up the private stairway (Silverthorne License 30796).

Sep. 18 – 25

$171 CAD per night

Guest favourite

Guest suite in Eagle

4.95 out of 5 average rating, 464 reviews

Adventurer's Paradise

Josh and I just built our first home in the last few years. We have a modern and clean down stairs lock off only 3 blocks from downtown. The space is all yours with a kitchen, bedroom, bathroom, laundry and private entrance with parking. We are in the center of Colorado's mountain biking community with a 100 miles of single track. Also just down the interstate from Vail and Beaver Creek resorts with more amazing mountain biking and skiing. The views alone are worth the visit! Lic. #006688

Oct. 8 – 15

$174 CAD per night

Guest favourite

Home in Como

4.97 out of 5 average rating, 385 reviews

Red's Retreat - Hot tub, pool table, so much more!

The entire cabin, game room and hot tub are yours! Pool table, dart board, Air Hockey, Propane Grill, Kitchen, Surround sound media area. South Park is famous for Gold Metal fishing, gold prospecting, hiking, off road recreation. Very unique place! Red's Retreat is 420 and prop.122 friendly to guest of legal age (21) in designated areas. We do not allow pets unless they are support animals. Note: predators are a constant danger to support animals so bring them at your own risk!

Oct. 23 – 30

$176 CAD per night

Guest favourite

Apartment in Carbondale

4.97 out of 5 average rating, 398 reviews

Gorgeous, Cozy, Mountain “Chalet” Private Hot Tub

Step into your private, light-filled one-bedroom apartment reminiscent of a cozy, ski chalet. PLEASE NOTE: The apartment is in the lower level of our home, we live upstairs with our dogs. Private, locked off entrance that opens onto a patio with hot tub and a huge, grassy, fenced yard, perfect for your dog! We offer many extras such as wine, coffee, amenities & snacks. Only 25 minutes from Aspen and Snowmass and 5 minutes to: City Market, Whole Foods, great restaurants and shopping.

Sep. 3 – 10

$251 CAD per night

Guest favourite

Guest suite in Buena Vista

4.84 out of 5 average rating, 696 reviews

Tucked Away Stay - Close To Town and In Nature

Come enjoy our private 5 acres of Pinon trees with the convenience of being 5 minutes from town. Enjoy the joys of children on property and views of incredible mountains with the wildlife that frequents our "back yard". Relax in our private guest area locked off from the rest of our home including a kitchenette and laundry area, all separated from the rest of the house by a custom built and locking doorway. We would love to have your pup join you. There is a $15 pet fee (max 2).

Oct. 11 – 18

$178 CAD per night

Guest favourite

Guest suite in Carbondale

4.89 out of 5 average rating, 268 reviews

Black Bear Guest Suite With Private Entrance

REMODELED garden-level guest suite with private entrance located just off Highway 82. This is the lower floor of a three floor single family home in a quiet, family friendly neighborhood. The space includes 2 bdrm, 1 bath and a large living area with a small couch, a hide-a-bed couch, TV, dining table, small kitchenette and laundry. Active family of 5 living upstairs. Use of fenced yard and hot tub are included. Midway between Aspen and Glenwood and only 3 blocks to bus stop.

Oct. 21 – 28

$235 CAD per night

Guest favourite

Cottage in Glenwood Springs

4.94 out of 5 average rating, 776 reviews

Mountain Cottage at Fourmile Creek

Only minutes from the beautiful town of Glenwood Springs, this mountain cottage offers privacy and country living at its finest. It boasts a unique, storybook architecture that is unparalleled. This custom built cottage is an outdoor lover's paradise! It is a quick hop and a skip from Sunlight Ski area-be on the chair lift in 5 minutes! The area offers plentiful ski runs, backcountry skiing, snowmobiling, snowshoeing, equestrian trails, mountain biking, and hiking.

Oct. 12 – 19

$233 CAD per night

Superhost

Condo in Vail

4.91 out of 5 average rating, 186 reviews

*Marriott's StreamSide Birch 1BD sleeps 4 -6

CHANNEL THE SPIRIT OF THE ROCKIES IN VAIL Set amid world-class ski slopes and year-round outdoor recreation, Marriott's StreamSide Birch at Vail invites you to play among the Colorado mountains. Ski 3,000 acres of fresh powder at Vail's Back Bowls, hike the lush White River National Forest, shop the boutiques at Cascade Village, raft dazzling rivers and enjoy endless leisure activities in the great outdoors, all while staying in one of our rental villas.

Sep. 12 – 19

$173 CAD per night

Guest favourite

Home in Parachute

4.94 out of 5 average rating, 156 reviews

Our Dream Ranch Guest Home

Our Dream Ranch sits on 70 gorgeous acres with room to hike to the Colorado River that borders our property. Relax at the stocked fishing pond or have a fire in our firepit. Golfing right across the road. Activity Center within 2 miles. Ski Resorts 45 minutes away. Very quiet and peaceful. You can bring horses for an additional fee of $20.00/horse/limit 2 horses. We have turn out available.

Apr. 29 – May 6

$186 CAD per night