Westside vacation rentals
We found 232 vacation rentals — enter your dates for availability
Select from 87 homes, 30 cottages, and other vacation rentals in Westside to find one that's perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the amenities you expect for your stay, which might include a garden and pool. No matter what you're looking for, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Westside
Showing deals for:Dec 11 - Dec 18

Exceptional
(11 reviews)
Luxury Garden Loft in Historic Old North End, Centrally located
Colorado Springs
$266
$1,859 for 7 nights
All fees included

Exceptional
(6 reviews)
9/9 - 11 Now available! 3 bedroom Downtown with Firepits and backyard
Colorado Springs
$156
$1,092 for 7 nights
All fees included

Exceptional
(7 reviews)
Green Grove at Captain's Cove, located in the heart of Old Colorado City 2
Colorado Springs
$135
$948 for 7 nights
All fees included

Exceptional
(21 reviews)
Stylish Boho cottage
Colorado Springs
$143
$1,000 for 7 nights
All fees included

Exceptional
(9 reviews)
Westside Stairway to a Haven in Old Colorado City at the base of Pikes Peak
Colorado Springs
$105
$734 for 7 nights
All fees included

Exceptional
(10 reviews)
In the Heart of OCC overlooking W. Colorado Ave-Electric Avenue @ Captain's Cove
Colorado Springs
$139
$975 for 7 nights
All fees included

Exceptional
(5 reviews)
Nautical Nook at Captain's Cove, Located in the heart of Old Colorado City
Colorado Springs
$133
$932 for 7 nights
All fees included
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Westside

9/9 - 11 Now available! 3 bedroom Downtown with Firepits and backyard
Sleeps 6 · 3 bedrooms · 1 bathroom

🗻Mountain VIEWS!❤️on Colorado Ave!❤️Walkable Neighborhood❤️Backyard❤️Fire Pit🔥
Sleeps 6 · 2 bedrooms · 1+ bathroom

Peakstone Nest! Pet-Friendly & Fire Pit, Workspace
Sleeps 8 · 3 bedrooms · 1 bathroom

9/13 - 15 now available Updated 2br Minutes from downtown- backyard & Firepits
Sleeps 6 · 2 bedrooms · 1 bathroom

The General Store- Private and centrally located
Sleeps 4 · 1 bedroom · 1 bathroom

Historic Westside Home: Central Location, AC & Game Room
Sleeps 14 · 4 bedrooms · 3+ bathrooms
Top rated rentals - Westside

Colorado Springs work project
The location was excellent for our work needs. The host J was very responsive and even installed gate for our dog to fence in the back yard. This make the stay extra special for our boxer Ivy who really enjoyed the outdoor space.The cottage is very well stocked with what you would need for a comfortable stay.
Francisca B.
Stayed Oct 2024

Fun Vibe
We spent one night in this cute home as we traveled between national parks with our 4 young adult kids. Everyone in our group had plenty of space to spread out and enjoy the entertainment it offered from ping pong to the outdoor space with the hot tub and corn hole. It was a great break from our strenuous hiking and skiing. The host was gracious and communication was excellent!
Kimberly W.
Stayed Apr 2024

Marvelous
Beautiful home, perfect location, excellent hosts. Could not have asked for more. Everything was as advertised, would highly recommend to anyone.
Stephen T.
Stayed Sep 2023

Beautiful home in a great location!
Amazing!
Denise K.
Stayed Oct 2020

Wonderful 2-bedroom Home in Old Colorado City
This 2 bedroom home is located within a 10 minute drive to Garden of the Gods, downtown Old Colorado City shops and restaurants, Manitou Springs, Pike’s Peak cog railway, Cheyenne Mountain zoo, hiking trails, and pretty much any other attractions a visitor to Colorado Springs might enjoy.
The property is clean and well-maintained. There is street in front of the home and alley parking in the rear, which is where we parked during our stay.
The living room and kitchen are clean and updated. The appliances are all newer, operational, and clean. While we did not bring our dogs, the property is pet friendly.
Both bedrooms are located upstairs and include queen beds (I believe) and window AC units, if visiting during the summer months. The couch in the living room has a pullout sleeper that is great for kids.
The host was friendly in her communications and has clear and super easy check in/out instructions and a “who-to-contact” list in case visitors have any questions or concerns.
We will try to stay here again the next time we visit Colorado Springs.
Alexander R.
Stayed Jul 2023
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Can I find a vacation rental in Westside?
Yes, we have vacation rentals near well known points of interest in Westside, or you can go with a more remote option if you'd like a relaxing place to stay.
How many vacation rentals are there in Westside?
With 87 Expedia vacation rentals, you're sure to find just the right place for your Westside stay.
What can I see and do in Westside?
Explore the area and family-friendly sights such as Cheyenne Mountain Zoo, or get out into nature at a spot like Garden of the Gods. Other popular places to visit in the area include Pikes Peak and US Air Force Academy.
What are vacation rentals like in Westside?
Vacation rentals are privately owned accommodations you can stay in for a short or long stay in Westside. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.
More Vacation Ideas
- Fort Carson Vacation Rentals
- Palmer Lake Vacation Rentals
- Manitou Springs Vacation Rentals
- Deckers Vacation Rentals
- Peyton Vacation Rentals
- West Colorado Springs Vacation Rentals
- Southeast Denver Vacation Rentals
- Broadmoor Vacation Rentals
- Green Mountain Falls Vacation Rentals
- Old Colorado City Vacation Rentals
- North Colorado Springs Vacation Rentals
- Colorado Springs Vacation Rentals
- Penrose Vacation Rentals
- Victor Vacation Rentals
- Downtown Colorado Springs Vacation Rentals
- Central Colorado Springs Vacation Rentals
- Colorado College Vacation Rentals
- Colorado Springs Vacation Rentals
- Southwest Vacation Rentals
- Monument Vacation Rentals
- Garden of the Gods Vacation Rentals
- Florissant Vacation Rentals
- Kissing Camels Vacation Rentals
- Old North End Vacation Rentals
- Cascade Vacation Rentals
- Manitou Springs Historic District Vacation Rentals
- Woodland Park Vacation Rentals
- Cripple Creek Vacation Rentals
- Royal Gorge Vacation Rentals
- Gold Belt Tour Scenic and Historic Byway Vacation Rentals
- Divide Vacation Rentals
- Canon City Vacation Rentals
- Fountain Vacation Rentals
- Larkspur Vacation Rentals
- Security-Widefield Vacation Rentals
- Usaf Academy Vacation Rentals
- Calhan Vacation Rentals
- Pet-Friendly rentals in Southeast Colorado Springs
- Lake rentals in Centennial
- Family rentals in Woodland Park
- Rentals with pool in North Colorado Springs
- Pet-Friendly rentals in Downtown Colorado Springs
- Oceanfront rentals in Royal Gorge
- Mountain rentals in Cripple Creek
- Beach rentals in Manitou Springs
- Rentals with hot tubs in Woodland Park
- Family rentals in Green Mountain Falls
- House rentals in Old Colorado City
- Longstay Hotels in Castle Rock
- Cottage rentals in Colorado Springs
- Family rentals in Cimarron Hills
- Rentals with pool in Colorado Springs
- Cabin rentals in Colorado Springs
- Beach rentals in Royal Gorge
- Family rentals in Colorado Springs
- Castle rentals in Royal Gorge
- Rentals with hot tubs in Green Mountain Falls
- Pet-Friendly rentals in Manitou Springs
- Cabin rentals in Colorado Springs
- Lake rentals in Monument
- Condo rentals in Old Colorado City
- Rv and caravan rentals in Royal Gorge
- Rentals with hot tubs in Manitou Springs
- Beach rentals in Colorado Springs
- Rentals with pool in Monument
- Condo rentals in Colorado Springs
- Pet-Friendly rentals in Colorado Springs
- Hotels in Royal Gorge
- Longstay Hotels in Cascade
- Lake rentals in Littleton
- Pet-Friendly rentals in Green Mountain Falls
- Rentals with hot tubs in Cascade
- Guest houses in Colorado Springs
- Guest houses in Northeast Colorado Springs
- Longstay Hotels in Woodland Park
- Ski-In/Ski-Out rentals in Royal Gorge
- Longstay Hotels in Broadmoor
- Rentals with pool in Manitou Springs
- Townhouse rentals in Broadmoor
- Longstay Hotels in Manitou Springs
- Chalet rentals in Colorado Springs
- Longstay Hotels in Colorado Springs (and vicinity)
- Mountain rentals in Green Mountain Falls
- Pet-Friendly rentals in Royal Gorge
- Family rentals in Manitou Springs
- Houseboat rentals in Royal Gorge
- Lake rentals in Woodland Park
- House rentals in Colorado Springs
- Cabin rentals in Castle Rock
- Bed and breakfasts in Colorado Springs
- Rentals with pool in Green Mountain Falls
- Lodge rentals in Green Mountain Falls
- Rentals with hot tubs in Colorado Springs
- Lake rentals in Castle Rock
- Townhouse rentals in Colorado Springs
- Mountain rentals in Royal Gorge
- Mountain rentals in Colorado Springs
- Mountain rentals in Manitou Springs
- Villa rentals in Canon City
- Cottage rentals in Broadmoor
