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 1 – 8

R3,498 ZAR per night

Guest favorite

Loft in Colorado Springs

4.99 out of 5 average rating, 437 reviews

THE LOFT- Unique, Historic, Majestic Views!

Our Loft is located in the heart of Old Colorado City (OCC). Just 5 mins from Manitou Springs & 5 mins to downtown Colorado Springs. The Loft exudes character from the ceilings, to the exposed brick walls, to the custom hardwood floors. The balcony overlooks city center & has stunning views of Pikes Peak. WALK TO EVERYTHING! Restaurants, shops & bars right out the front door. Due to location, there is potential for noise. NO ELEVATOR. NO PETS/SMOKING ID REQUIRED ON PROFILE/21+ NO PARTIES/EVENTS

Jan 11 – 18

R2,924 ZAR per night

Guest favorite

Guest suite in Colorado Springs

4.91 out of 5 average rating, 367 reviews

Hiking | Dining | Nightlife in Historic Ivywild

★ 2 miles to Downtown ★ 2 miles to Cheyenne Canon (tons of hiking) ★ 1.3 miles to 5 star Broadmoor Hotels (conference center) ★ 10 minute walk to the Historic Ivywild School (restaurants, cocktails, and local beer) ★ Quick drive to CO College, Garden of the Gods, Pikes Peak, USAFA, UCCS ★ Equipped kitchen w/ coffee maker, water kettle, coffee/tea and more! ★ Family Friendly: Pack 'n play, Baby monitor, and booster seat ★ WORK TRAVEL: FAST WIFI and designated desk space ★ 5 star cleaning rating

Oct 9 – 16

R2,257 ZAR per night

Guest favorite

Home in Woodland Park

4.82 out of 5 average rating, 134 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 25 – May 2

R12,924 ZAR 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

Apr 6 – 13

R1,792 ZAR per night

Superhost

Guest suite in Colorado Springs

4.87 out of 5 average rating, 1091 reviews

⫸Cozy Retreat⫷ Fire Pit┃Peloton┃Corn Hole┃Hot Tub

Cozy In-law apt perfect for just one or two people packing a punch: massive shower, fireplace, record player, Roku TV (Hulu/Netflix) & comfiest bed! ★Walk to OTC; Short drive Dwntwn, CC, Pikes Peak, USAFA, UCCS ★YARD: Hot tub, firepit, grill, speaker, yard games, Schwinn bike ★GYM: Peloton, Treadmill & Elliptical. Jump ropes, kettle bells, speaker, Roku TV+MORE! ★DESK: printer, fast WIFI, G00gle Mini & cocktail shaker ★FAMILY: PackNplay, toys, high chair ★Kitchenette: stovetop, blender+more!

Jan 29 – Feb 5

R2,103 ZAR 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

R2,823 ZAR per night

Guest favorite

Guesthouse in Colorado Springs

4.97 out of 5 average rating, 813 reviews

Cozy Solar Cottage on the West Side

My cottage is centrally located, close to downtown--within walking distance. Garden of the Gods, road to Pikes Peak, & Colorado College are minutes away. The interior is quaint and cozy, but has a roomy kitchen, fully stocked for preparing food. The outdoor space is peaceful and relaxing. I have a detailed list of restaurants & things to do. You'll love the access to an urban trail (Monument Valley), comfy queen bed, & coffee. A coffee shop and breakfast place are within walking distance.

Apr 15 – 22

R1,395 ZAR 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.

Jun 3 – 10

R2,016 ZAR 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.

Nov 1 – 8

R3,642 ZAR 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.

Dec 3 – 10

R5,323 ZAR 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

Jul 22 – 29

R1,892 ZAR per night