Holiday Homes in Woodland Park

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Featured Holiday Homes in Woodland Park

Vibrant Watermelon! Hot Tub & King Bed & BBQ!

9.8 out of 10, Exceptional, (11)
"This was a clean and nice comfy property. Modern and with a lot of options to cook and a nice tv that you could connect your devices to. Not to mention the hot tub was nice! "
Vibrant Watermelon! Hot Tub & King Bed & BBQ!

Secluded Modern Mountain Home, Views, Wifi, Hot Tub

9.4 out of 10, Exceptional, (50)
"The house is beautiful, clean, perfect view."
Secluded Modern Mountain Home, Views, Wifi, Hot Tub

Great remodeled Downtown Manitou Springs Home Lic#9244

9.2 out of 10, Wonderful, (131)
"My wife and I enjoyed a great weekend in Manitou for the Emily Crawford Coffin Races. Perfect location for the races! Great house! Will do this again! "
Great remodeled Downtown Manitou Springs Home Lic#9244

Whispering Pines - LUXURY Cabin-Hot Tub, Fireplace, Huge Deck, Pool Tbl, 6 Acres

10.0 out of 10, Exceptional, (230)
"The weather did not cooperate for the beginning of our stay. Michael went above and beyond to communicate with us and do whatever he could to get us into the house. We were able to get in a day after the initial date we booked and that was only possible due to his efforts to get the house cleaned and driveway cleared. It was a great house to be snowed in for a couple of days. "
Whispering Pines - LUXURY Cabin-Hot Tub, Fireplace, Huge Deck, Pool Tbl, 6 Acres

New! Broadmoor Reserve Home, Mountainside views, Deck. A-STRP-24-0585

10.0 out of 10, Exceptional, (16)
"We reserved this home because it is close to our house, and we had out of state family visiting. It was better than i ever imagined! This home was very well appointed and super comfortable for everyone from 4 years old to 40❣️. There were games, plenty of open space for gatherings, a beautiful yard to play in, and the views of Cheyenne Mountain were spectacular!! Many thanks to our awesome Hosts, and i hope to reserve again soon❤️"
New! Broadmoor Reserve Home, Mountainside views, Deck. A-STRP-24-0585

Enjoy Downtown Colorado Springs Restaurants, Breweries, Museums, Galleries

8.8 out of 10, Excellent, (126)
"The house is convenient to downtown Colorado Springs, making it easy to access everything we needed. There were great dining options within walking distance. However, the home is smaller than the photos suggest. It was clean and decently stocked, but the living room couch was replaced with an uncomfortable IKEA sofa that fits only 4 people closely. The only other seating options are the 3 wooden chairs and 2 decorative chairs in the dining area. All beds were uncomfortable and felt like sleeping...
The price is AU$316
includes taxes & fees
2 Dec - 3 Dec
Enjoy Downtown Colorado Springs Restaurants, Breweries, Museums, Galleries

Captain Jack’s Cottage in Beautiful Cheyenne Cañon 2 blocks from Broadmoor Hotel

10.0 out of 10, Exceptional, (212)
"Great place to stay, owners were so accommodating. Quiet area. House has everything you need to feel at home. Loved the place!!!"
Captain Jack’s Cottage in Beautiful Cheyenne Cañon 2 blocks from Broadmoor Hotel

Near Downtown« Hot Tub┃Firepit┃Fenced Yard

10.0 out of 10, Exceptional, (33)
"The property met our needs quite well -- friends and family coming to town for a concert. We were not in the house enough time to utilize the hot tub or fire pit."
Near Downtown« Hot Tub┃Firepit┃Fenced Yard

🌟Award Winning 1923 Downtown Bungalow - Pikes Peak Garden of the Gods & Hot Tub!

10.0 out of 10, Exceptional, (278)
"This place was awesome! Loved the cozy home and the much appreciated relaxing atmosphere!"
The price is AU$706
includes taxes & fees
2 Dec - 3 Dec
🌟Award Winning 1923 Downtown Bungalow - Pikes Peak Garden of the Gods & Hot Tub!

Close to EVERYTHING! Beautiful Farmhouse Retreat!

9.8 out of 10, Exceptional, (134)
"Fantastic location. Mountain View was awesome. Walked around the old colorado city area shops and restaurants. Close to Manitou Springs, Gardens of the gods and pikes peak. House was everthing advertised."
The price is AU$566
includes taxes & fees
30 Nov - 1 Dec
Close to EVERYTHING! Beautiful Farmhouse Retreat!

Travelers Gym! Fire Pit, Arcade, Pets, Prime Spot!

8.8 out of 10, Excellent, (10)
"Wonderful stay and everything was very clean. We were close to alot of the places we wanted to visit."
Travelers Gym! Fire Pit, Arcade, Pets, Prime Spot!

Townhouse, close I25, Air Force Academy, walk to restaurants, movies, bowling

10.0 out of 10, Exceptional, (105)
"Probably our favorite VRBO ever! Spotless, comfortable and amazing location. We visited our cadet. We will definitely be back!! Thank you!!"
Townhouse, close I25, Air Force Academy, walk to restaurants, movies, bowling

Frank's Flat

9.8 out of 10, Exceptional, (19)
"Close to downtown and owner was wonderful to work with "
Frank's Flat

The Vibrant Victorian! BBQ grill & Fire Pit in OCC!

9.0 out of 10, Wonderful, (11)
"Small home on shared lot with fenced backyard with hot tub. Old home but outfitted fine for our visit. Walkable neighborhood with nearby park. Really close to downtown for easy access to various charming restaurants, Olympic museum, Garden of the Gods, Manitou Springs and more. The professional management had pretty seamless check in and check out. Breaker went out on first evening and while we got responses, I’m not sure the message sender was a person so the fix instructions were a bit...
The Vibrant Victorian! BBQ grill & Fire Pit in OCC!

Modern Paradise Dog Friendly Getaway

10.0 out of 10, Exceptional, (7)
"Great place for a girls weekend. A quick drive to shopping and dining. "
The price is AU$429
includes taxes & fees
3 Dec - 4 Dec
Modern Paradise Dog Friendly Getaway

Family Reunion on a 5-bedroom house in heart of Colorado Springs close to AFB

10.0 out of 10, Exceptional, (1)
"We had so much fun "
The price is AU$779
includes taxes & fees
2 Dec - 3 Dec
Family Reunion on a 5-bedroom house in heart of Colorado Springs close to AFB

Majestic Lodge only 22 miles from the base of Pike's Peak

9.8 out of 10, Exceptional, (117)
"Middle of nowhere. Exactly what we needed. "
Majestic Lodge only 22 miles from the base of Pike's Peak

Mountain Views with Hot Tub

10.0 out of 10, Exceptional, (33)
"Check in went smoothly, and we found the home to be spacious and clean, and the kitchen stocked with plenty of appliances, utensils, spices etc. We liked some of the items provided so much that we will be purchasing some of them ourselves for our own home: shampoo, conditioner, lotion etc. The views were amazing and instructions clearly posted throughout the home. It was close to grocery stores, restaurants, shops etc. but the access roads getting to the neighborhood were a bit rough. We had...
The price is AU$705
includes taxes & fees
2 Dec - 3 Dec
Mountain Views with Hot Tub

Mountain Retreat, Tall Pines, Hot Tub, WiFi, Log Furnishings & Wildlife!

10.0 out of 10, Exceptional, (339)
"We loved our stay in the cabin. Deer were everywhere and the lake was a nice walk away. The cabin was clean and had everything we needed!"
Mountain Retreat, Tall Pines, Hot Tub, WiFi, Log Furnishings & Wildlife!

Charming Creekside 2BR/2BA/Kitchen @ Pikes Peak

9.4 out of 10, Exceptional, (10)
"Place was great with the creek outside. Perfect location. "
The price is AU$407
includes taxes & fees
1 Dec - 2 Dec
Charming Creekside 2BR/2BA/Kitchen @ Pikes Peak
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Woodland Park

Majestic Lodge only 22 miles from the base of Pike's Peak

9.8 out of 10, Exceptional, (117)
"Middle of nowhere. Exactly what we needed. "
Majestic Lodge only 22 miles from the base of Pike's Peak

Mountain Views with Hot Tub

10.0 out of 10, Exceptional, (33)
"Check in went smoothly, and we found the home to be spacious and clean, and the kitchen stocked with plenty of appliances, utensils, spices etc. We liked some of the items provided so much that we will be purchasing some of them ourselves for our own home: shampoo, conditioner, lotion etc. The views were amazing and instructions clearly posted throughout the home. It was close to grocery stores, restaurants, shops etc. but the access roads getting to the neighborhood were a bit rough. We had...
The price is AU$705
includes taxes & fees
2 Dec - 3 Dec
Mountain Views with Hot Tub

Cabin on 10 acres with private hot tub, views of Pikes Peak

9.6 out of 10, Exceptional, (94)
"Beautiful property, private comfy. My husbands and my 15 year anniversary so we just used the main bedroom. Heated floors were amazing. Looked like all the rooms were nice. We were not there much, but the hot tub at night with the stream and stars absolutely blew me away!!!"
Cabin on 10 acres with private hot tub, views of Pikes Peak
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.