Family-friendly vacation rentals in Woodland Park

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Top-rated family-friendly rentals in Woodland Park

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

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Guest favorite

Cabin in Divide

4.89 out of 5 average rating, 268 reviews

Pineridge Cabin

Pineridge Cabin is a cozy honeymooner's get-away nestled on a wooded hillside at 9,400 feet above sea level. It is located nine miles from Cripple Creek, to the south, and nine miles from Divide, to the north, and thirty-fives miles west of downtown Colorado Springs. Approximately forty-five miles from the Colorado Springs Airport and 122 miles from the Denver International Airport. It offers all of the amenities of home except a washer and dryer but the scenery and views well make up for it.

Apr 14 – 21

G$39,351 GYD per night

Guest favorite

Home in Woodland Park

4.82 out of 5 average rating, 133 reviews

Woodland Escape~3Acres of CO Mt. life~Min to town

"The Woodland Escape" sits secluded on 3 private acres of quintessential Colorado land, but is less than 2 minutes away from town, offering you the best of both worlds. This location offers many activities to keep you busy all week long! Hike to the top of the private land, and get picturesque views of Pike's Peak. House offers a fire pit, foosball, air hockey, 110" projector screen and a hot tub! House is within 20 minutes of CO Springs area. Small events are allowed at an additional fee.

Apr 22 – 29

G$145,379 GYD per night

Guest favorite

Cabin in Woodland Park

4.86 out of 5 average rating, 333 reviews

Cabin In Woodland Park with Pikes Peak View

Our Cabin was built in 1947, it is a bit of Country but was recently updated with a modern flair with cool interior barn doors and decor, but we kept the nuts and bolts of the 1940's design. It has an incredible view of Pikes Peak, Woodland Park has many restaurants, family-friendly activities. Only 25 Minutes to Colorado Springs. The Cabin is good for couples, solo adventurers, and furry friends. The cabin is cute and cozy and located just off Main Street in Woodland Park. License # 329434

Dec 7 – 14

G$19,123 GYD per night

Guest favorite

Cabin in Cripple Creek

4.93 out of 5 average rating, 302 reviews

Secluded Mountain Cabin, WiFi, Gorgeous Views!

The Bears Den is a secluded cabin nestled on a hillside in the midst of tall pines and beautiful aspens, just 10 minutes from the historic mining and casino town of Cripple Creek. Enjoy magnificent views of Mt. Pisgah and surrounding mountain ranges from every window. We have made the Den very cozy with its 3 bedrooms, 2 baths, a game room, and a back deck with a grill and seating. Special touches from Renee and Michael make your romantic getaway or family stay an unforgettable experience.

May 9 – 16

G$31,755 GYD per night

Guest favorite

Guest suite in Monument

4.95 out of 5 average rating, 261 reviews

Windsong Suite~15 min to USAFA~2bed/2bath

New name, new furniture, same wonderful Peaceful Forest Retreat! Mother-in-law suite attached to our home in Pike National Forest! Serene living space complete w/ 2 bed, 2 bath, living room, kitchenette (no stove), deck, TV, internet & deer! Enjoy our secluded forest setting with easy access to the fun sites in Colorado Springs & the Urban delights of Denver. Relax on the deck of our wooded retreat with your morning coffee or while you grill & play corn hole after a fun day of exploring.

Mar 29 – Apr 5

G$27,698 GYD per night

Guest favorite

Cabin in Larkspur

4.98 out of 5 average rating, 123 reviews

Lodge and Pinecone Hollow-sleeps 4+ & 420 friendly

Pinecone Hollow is nestled right in between Denver and Colorado Springs & has been carefully set up for those who love nature, open spaces, outdoor activities and/or just stay in and enjoy the quiet of remote living. If you want to be "Off the Grid" or just get a reprieve from the daily grind of city life, this place is it. Quiet nights, plenty of wildlife & beautiful scenic views. There is WiFi, DISH T.V and more!!! Hiking, scenic drives, bird watching, puzzles and so much more to do!

Oct 4 – 11

G$31,153 GYD per night

Guest favorite

Guest suite in Monument

4.93 out of 5 average rating, 235 reviews

Private Lower Level Suite with Peak Views

Clean, cozy, and comfortable private walkout basement apartment with gorgeous views of Pikes Peak and the Air Force Academy. Large bedroom with comfortable queen bed, recently updated full bathroom, kitchenette (please note, no oven or cook top), and large living space with Roku tv, fireplace, and room for more to sleep and hang out. Located in a quiet neighborhood approx. 2 miles from the Air Force Academy, with easy highway access for activities in both Denver and Colorado Springs.

Oct 9 – 16

G$22,914 GYD per night

Guest favorite

Apartment in Colorado Springs

5.0 out of 5 average rating, 285 reviews

Cozy Garden Level Studio Apt near Downtown CS

Safe, end-of-street home w/no traffic. Sunny, private, garden level apt w/ private entrance. Queen bed, & love-seat futon opens to a single comfy bed; private bath. Full kitchen to prepare your meals. Organic coffee & teas, condiments, filtered water. Yoga mats & essential oils. Please, NO smoking in apt. Attention to detail & artwork make this bungalow a comfortable, home-like environment. I'm very flexible w/ check-in/out times, as I know flights & long drives can be challenging.

Jul 29 – Aug 3

G$13,176 GYD per night

Guest favorite

Townhouse in Colorado Springs

4.88 out of 5 average rating, 669 reviews

Private Cozy Home Walk to Garden of the Gods

This sunny home on the border of Manitou Springs is the quintessential small town getaway. It is a short walk to Garden of the Gods park which makes it convenient for exploring. We intentionally provide most everything you need for a comfortable, relaxing stay. Enjoy the best of Colorado Springs - hike, explore, or simply relax in nature. It is the perfect home base for visitors of US Olympic Training Center, Pikes Peak, Manitou Springs, Colorado College, UCCS, Seven Falls, and more.

Jan 15 – 22

G$26,156 GYD per night

Guest favorite

Cabin in Florissant

4.92 out of 5 average rating, 446 reviews

Fawn Cabin, On 5 Private Acres With Hot Tub!

Fawn Cabin is an authentic mountain cabin that truly says Colorado! Set on 5+ acres with beautiful views and privacy. Enjoy the relaxing sounds of nature from the deck, soak in the hot tub, and just relax. Enjoy viewing the deer and other abundant wildlife that are right outside the door. Just 20 minutes from Cripple Creek, 20 minutes from the South Platte river in Eleven Mile Canyon, 10 minutes from Florissant Fossil Beds. Two hours from Denver. One hour from Colo Spgs.

Jan 5 – 12

G$40,967 GYD per night

Guest favorite

Home in Woodland Park

4.98 out of 5 average rating, 208 reviews

Black Bear Cabin above the Clouds, Woodland Park

This charming and luxurious cabin above the clouds offers all the amenities you want and all the space you need. This idyllic cabin is perfect for couples’ trips, family getaways, or snowy retreats with old friends. Just a short walk from town, Black Bear Lodge offers plenty of attractions and activities. For those looking for rest and relaxation, the storybook cabin features an open-concept kitchen with space to cook, room to chat, and a relaxing hot tub.

Oct 18 – 25

G$78,438 GYD per night

Guest favorite

Guesthouse in Palmer Lake

4.95 out of 5 average rating, 207 reviews

Quaint and Historic Studio Cabin

Rustic and eco-friendly this studio guesthouse overlooks the quaint town of Palmer Lake. Within walking distance of all sorts of outdoor recreation and wonderful restaurants. We're a short driving distance from Colorado Springs and the US Air Force Academy, Garden of the Gods and Pikes Peak region. It's the perfect place to relax and recreate while maintaining distance and privacy. We look forward to hosting you! Becky and Phil

May 30 – Jun 4

G$23,994 GYD per night