Photo by Ryan Carlos
Westside holiday homes
We found 234 holiday rentals — enter your dates for availability
Discover a selection of 95 homes, 28 apartments and other holiday rentals in Westside that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you need and want for your stay, such as air conditioning and Wi-Fi. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Westside
Showing deals for:23 Jan - 30 Jan
Image gallery for The Cozy Cottage
1010 out of 10, Exceptional, (143 reviews)
Exceptional
(143 reviews)
The Cozy Cottage
Colorado Springs, CO
8% off
Price is NZ$1,441
NZ$1,441
for 7 nights, 1 cottage
NZ$206 per night
includes taxes & fees
Image gallery for Central Colorado Springs Home w/ Alluring Backyard
9.49.4 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Central Colorado Springs Home w/ Alluring Backyard
Colorado Springs, CO
10% off
Price is NZ$2,218
NZ$2,218
for 7 nights, 1 home
NZ$317 per night
includes taxes & fees
Image gallery for Newly Remodeled Pet Friendly Cottage
8.68.6 out of 10, Excellent, (108 reviews)
Excellent
(108 reviews)
Newly Remodeled Pet Friendly Cottage
Colorado Springs, CO
7% off
Price is NZ$1,323
NZ$1,323
for 7 nights, 1 cottage
NZ$189 per night
includes taxes & fees
Image gallery for Cascading Manor! Mansion & Guesthouse w Fire Pit
8.68.6 out of 10, Excellent, (8 reviews)
Excellent
(8 reviews)
Cascading Manor! Mansion & Guesthouse w Fire Pit
Colorado Springs, CO
5% off
Price is NZ$5,830
NZ$5,830
for 7 nights, 1 villa
NZ$833 per night
includes taxes & fees
Image gallery for Kindred Courtyard! Historic Stay w BBQ & Fire Pit
9.69.6 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Kindred Courtyard! Historic Stay w BBQ & Fire Pit
Colorado Springs, CO
5% off
Price is NZ$1,721
NZ$1,721
for 7 nights, 1 apartment
NZ$246 per night
includes taxes & fees
Image gallery for Cozy Solar Cottage on the West Side
1010 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)
Cozy Solar Cottage on the West Side
Colorado Springs, CO
7% off
Price is NZ$1,128
NZ$1,128
for 7 nights, 1 cottage
NZ$161 per night
includes taxes & fees
Image gallery for Highland Heights! Luxe Mountain VIEWS w/ Hot Tub
9.49.4 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Highland Heights! Luxe Mountain VIEWS w/ Hot Tub
Colorado Springs, CO
6% off
Price is NZ$10,428
NZ$10,428
for 7 nights, 1 home
NZ$1,490 per night
includes taxes & fees
Image gallery for 3BD Family Vacation Home Near Hiking & Downtown
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
3BD Family Vacation Home Near Hiking & Downtown
Colorado Springs, CO
6% off
Price is NZ$2,482
NZ$2,482
for 7 nights, 1 home
NZ$355 per night
includes taxes & fees
Image gallery for 4BD Westside Vacation Home w/Space & Flexibility
9.89.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
4BD Westside Vacation Home w/Space & Flexibility
Colorado Springs, CO
6% off
Price is NZ$3,334
NZ$3,334
for 7 nights, 1 home
NZ$476 per night
includes taxes & fees
Image gallery for 4BD Pikes Peak Views | Minutes to Hiking & Dining!!
9.69.6 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
4BD Pikes Peak Views | Minutes to Hiking & Dining!!
Colorado Springs, CO
6% off
Price is NZ$3,334
NZ$3,334
for 7 nights, 1 home
NZ$476 per night
includes taxes & fees
Image gallery for Miners Anvil! Steps to Historic District & OCC
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Miners Anvil! Steps to Historic District & OCC
Colorado Springs, CO
5% off
Price is NZ$1,691
NZ$1,691
for 7 nights, 1 apartment
NZ$242 per night
includes taxes & fees
Image gallery for Stylish Boho cottage
9.89.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Stylish Boho cottage
Colorado Springs, CO
11% off
Price is NZ$1,949
NZ$1,949
for 7 nights, 1 apartment
NZ$278 per night
includes taxes & fees
Image gallery for Designer Retreat | walk to brewery & cafés
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Designer Retreat | walk to brewery & cafés
Colorado Springs, CO
7% off
Price is NZ$2,147
NZ$2,147
for 7 nights, 1 home
NZ$307 per night
includes taxes & fees
Image gallery for In the Heart of OCC overlooking W. Colorado Ave-Electric Avenue @ Captain's Cove
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
In the Heart of OCC overlooking W. Colorado Ave-Electric Avenue @ Captain's Cove
Colorado Springs, CO
11% off
Price is NZ$1,846
NZ$1,846
for 7 nights, 1 apartment
NZ$264 per night
includes taxes & fees
Image gallery for Downtown Victorian Home, Large Group Space, 5BR, 7 Parking Spots, Pet Friendly!
9.89.8 out of 10, Exceptional, (210 reviews)
Exceptional
(210 reviews)
Downtown Victorian Home, Large Group Space, 5BR, 7 Parking Spots, Pet Friendly!
Colorado Springs, CO
8% off
Price is NZ$6,965
NZ$6,965
for 7 nights, 1 home
NZ$995 per night
includes taxes & fees
Image gallery for 2BR Old Colorado City Dog Friendly!
9.29.2 out of 10, Wonderful, (15 reviews)
Wonderful
(15 reviews)
2BR Old Colorado City Dog Friendly!
Colorado Springs, CO
6% off
Price is NZ$2,091
NZ$2,091
for 7 nights, 1 home
NZ$299 per night
includes taxes & fees
Image gallery for Pet Friendly Cottage located between Old Colorado City and Downtown!
9.89.8 out of 10, Exceptional, (77 reviews)
Exceptional
(77 reviews)
Pet Friendly Cottage located between Old Colorado City and Downtown!
Colorado Springs, CO
6% off
Price is NZ$1,739
NZ$1,739
for 7 nights, 1 cottage
NZ$248 per night
includes taxes & fees
Image gallery for Two Bedroom Home in the Heart of West Colorado Springs
9.89.8 out of 10, Exceptional, (184 reviews)
Exceptional
(184 reviews)
Two Bedroom Home in the Heart of West Colorado Springs
Colorado Springs, CO
8% off
Price is NZ$2,009
NZ$2,009
for 7 nights, 1 home
NZ$287 per night
includes taxes & fees
Image gallery for Vibrant Watermelon! Hot Tub & King Bed & BBQ!
9.69.6 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Vibrant Watermelon! Hot Tub & King Bed & BBQ!
Colorado Springs, CO
5% off
Price is NZ$2,097
NZ$2,097
for 7 nights, 1 home
NZ$300 per night
includes taxes & fees
Image gallery for Peak Pool Hall! Billiards Room & BBQ & Fire Pit!
9.09.0 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
Peak Pool Hall! Billiards Room & BBQ & Fire Pit!
Colorado Springs, CO
5% off
Price is NZ$1,866
NZ$1,866
for 7 nights, 1 home
NZ$267 per night
includes taxes & fees
Image gallery for Cozy home near downtown Colorado Springs and Old Colorado City
9.89.8 out of 10, Exceptional, (75 reviews)
Exceptional
(75 reviews)
Cozy home near downtown Colorado Springs and Old Colorado City
Colorado Springs, CO
7% off
Price is NZ$1,391
NZ$1,391
for 7 nights, 1 home
NZ$199 per night
includes taxes & fees
Image gallery for Station 130! Cozy Downtown Home w/ Fire Pit
9.69.6 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Station 130! Cozy Downtown Home w/ Fire Pit
Colorado Springs, CO
5% off
Price is NZ$1,504
NZ$1,504
for 7 nights, 1 home
NZ$215 per night
includes taxes & fees
Image gallery for Old Colorado City Get Away
8.88.8 out of 10, Excellent, (46 reviews)
Excellent
(46 reviews)
Old Colorado City Get Away
Colorado Springs, CO
8% off
Price is NZ$1,774
NZ$1,774
for 7 nights, 1 home
NZ$253 per night
includes taxes & fees
Image gallery for Custom Dream Home/ loft&porch/ trendy neighborhood
9.49.4 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Custom Dream Home/ loft&porch/ trendy neighborhood
Colorado Springs, CO
7% off
Price is NZ$2,874
NZ$2,874
for 7 nights, 1 home
NZ$411 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Westside
Colorado Cottage! Downtown, OCC w Patio!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Downtown & OCC!, Beautiful Mountain Views, AC!, OS Parking, Wifi
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
124 reviews(124 reviews)
🗻Mountain VIEWS!❤️on Colorado Ave!❤️Walkable Neighborhood❤️Backyard❤️Fire Pit🔥
Sleeps 6 · 2 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Kindred Courtyard! Historic Stay w BBQ & Fire Pit
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
February 2026 available Updated 2br Minutes from downtown- backyard & Firepits
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Blue Barn West Side Getaway mins to center, trails
Sleeps 10 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
Can I find a holiday rental in Westside?
Yes, there are holiday rentals close to the most popular sights in Westside, or you can select a more secluded option if you're looking for a relaxing stay.
How many holiday rentals are there in Westside?
With 95 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Westside?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westside. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.