Photo by Ryan Carlos
Westside holiday homes
We found 238 holiday rentals — enter your dates for availability
Discover a selection of 95 homes, 27 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:29 Aug - 5 Sept
Image gallery for Crescent Mansion! Walk DT, Hot Tub, Golf, BBQ
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Crescent Mansion! Walk DT, Hot Tub, Golf, BBQ
Colorado Springs, Colorado
6% off
Price is NZ$10,300
NZ$10,300
NZ$1,471 per night
includes taxes & fees
Image gallery for Epic Views: Modern, Rooftop Lounge, Prime Area!
8.88.8 out of 10 rating
Excellent
(24 reviews)
Epic Views: Modern, Rooftop Lounge, Prime Area!
Colorado Springs, CO
7% off
Price is NZ$7,641
NZ$7,641
NZ$1,092 per night
includes taxes & fees
Image gallery for Designer Retreat | walk to brewery & cafés
1010 out of 10 rating
Exceptional
(5 reviews)
Designer Retreat | walk to brewery & cafés
Colorado Springs, CO
8% off
Price is NZ$3,944
NZ$3,944
NZ$563 per night
includes taxes & fees
Image gallery for Blue Barn West Side Getaway mins to center, trails
1010 out of 10 rating
Exceptional
(105 reviews)
Blue Barn West Side Getaway mins to center, trails
Colorado Springs, CO
8% off
Price is NZ$6,298
NZ$6,298
NZ$900 per night
includes taxes & fees
Image gallery for Epic Views! Rooftop Lounge Firepit, Prime Spot
8.08.0 out of 10 rating
Very good
(13 reviews)
Epic Views! Rooftop Lounge Firepit, Prime Spot
Colorado Springs, CO
7% off
Price is NZ$6,459
NZ$6,459
NZ$923 per night
includes taxes & fees
Image gallery for Station 130! Family Home w Workspace & Fire Pit
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Station 130! Family Home w Workspace & Fire Pit
Colorado Springs, Colorado
6% off
Price is NZ$2,817
NZ$2,817
NZ$402 per night
includes taxes & fees
Image gallery for Cozy & Remodeled Steps to Downtown & OCC w/firepit
8.88.8 out of 10 rating
Excellent
(5 reviews)
Cozy & Remodeled Steps to Downtown & OCC w/firepit
Colorado Springs, CO
8% off
Price is NZ$4,009
NZ$4,009
NZ$573 per night
includes taxes & fees
Image gallery for Pinewood Meadow & Scenic Hot Tub & BBQ & Outdoors
9.49.4 out of 10 rating
Exceptional
(24 reviews)
Pinewood Meadow & Scenic Hot Tub & BBQ & Outdoors
Colorado Springs, Colorado
6% off
Price is NZ$8,144
NZ$8,144
NZ$1,163 per night
includes taxes & fees
Image gallery for The General Store- Private and centrally located
9.49.4 out of 10 rating
Exceptional
(6 reviews)
The General Store- Private and centrally located
Colorado Springs, CO
7% off
Price is NZ$2,202
NZ$2,202
NZ$315 per night
includes taxes & fees
Image gallery for Pet Friendly Cottage located between Old Colorado City and Downtown!
9.89.8 out of 10 rating
Exceptional
(72 reviews)
Pet Friendly Cottage located between Old Colorado City and Downtown!
Colorado Springs, CO
6% off
Price is NZ$2,091
NZ$2,091
NZ$299 per night
includes taxes & fees
Image gallery for Custom Dream Home/ loft&porch/ trendy neighborhood
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Custom Dream Home/ loft&porch/ trendy neighborhood
Colorado Springs, CO
8% off
Price is NZ$5,195
NZ$5,195
NZ$742 per night
includes taxes & fees
Image gallery for Pinewood Sanctuary Secluded & Peaceful OCC Oasis
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Pinewood Sanctuary Secluded & Peaceful OCC Oasis
Colorado Springs, Colorado
6% off
Price is NZ$3,596
NZ$3,596
NZ$514 per night
includes taxes & fees
Image gallery for Kiowa Peak! OCC & Downtown Basecamp
8.68.6 out of 10 rating
Excellent
(9 reviews)
Kiowa Peak! OCC & Downtown Basecamp
Colorado Springs, Colorado
6% off
Price is NZ$3,401
NZ$3,401
NZ$486 per night
includes taxes & fees
Image gallery for Miners Escape! Timeless District Cozy Haven
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Miners Escape! Timeless District Cozy Haven
Colorado Springs, Colorado
6% off
Price is NZ$4,588
NZ$4,588
NZ$655 per night
includes taxes & fees
Image gallery for Blast From The Past! Est 1898 A+ Spot Pet-Friendly
8.28.2 out of 10 rating
Very good
(15 reviews)
Blast From The Past! Est 1898 A+ Spot Pet-Friendly
Colorado Springs, Colorado
7% off
Price is NZ$4,910
NZ$4,910
NZ$701 per night
includes taxes & fees
Image gallery for Modern 2 bedroom in old Colorado City
8.48.4 out of 10 rating
Very good
(17 reviews)
Modern 2 bedroom in old Colorado City
Colorado Springs, CO
8% off
Price is NZ$3,534
NZ$3,534
NZ$505 per night
includes taxes & fees
Image gallery for Skyline Overlook! Panoramic Views & Hot Tub!
8.88.8 out of 10 rating
Excellent
(6 reviews)
Skyline Overlook! Panoramic Views & Hot Tub!
Colorado Springs, Colorado
6% off
Price is NZ$7,543
NZ$7,543
NZ$1,078 per night
includes taxes & fees
Image gallery for Colorado Cottage! Downtown, OCC w Patio!
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Colorado Cottage! Downtown, OCC w Patio!
Colorado Springs, Colorado
6% off
Price is NZ$3,646
NZ$3,646
NZ$521 per night
includes taxes & fees
Image gallery for Pinewood Treehouse! King Suite Scenic Worksation
8.88.8 out of 10 rating
Excellent
(11 reviews)
Pinewood Treehouse! King Suite Scenic Worksation
Colorado Springs, Colorado
6% off
Price is NZ$2,227
NZ$2,227
NZ$318 per night
includes taxes & fees
Image gallery for Hot Tub! Walk to Historic Old Colorado City & Shops.
9.69.6 out of 10 rating
Exceptional
(158 reviews)
Hot Tub! Walk to Historic Old Colorado City & Shops.
Colorado Springs, CO
8% off
Price is NZ$3,046
NZ$3,046
NZ$435 per night
includes taxes & fees
Image gallery for Baby Blue! Hot Tub! Elegant Kitchen & Bathrooms!
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Baby Blue! Hot Tub! Elegant Kitchen & Bathrooms!
Colorado Springs, Colorado
6% off
Price is NZ$6,272
NZ$6,272
NZ$896 per night
includes taxes & fees
Image gallery for Crescent Penthouse! Holiday Home w Hot Tub & Golf
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Crescent Penthouse! Holiday Home w Hot Tub & Golf
Colorado Springs, Colorado
6% off
Price is NZ$5,640
NZ$5,640
NZ$806 per night
includes taxes & fees
Image gallery for Vibrant Watermelon! Hot Tub & King Bed & BBQ!
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Vibrant Watermelon! Hot Tub & King Bed & BBQ!
Colorado Springs, Colorado
6% off
Price is NZ$4,559
NZ$4,559
NZ$651 per night
includes taxes & fees
Image gallery for 2 BDS Garden Of Gods - Near it all
9.09.0 out of 10 rating
Wonderful
(14 reviews)
2 BDS Garden Of Gods - Near it all
Colorado Springs, CO
7% off
Price is NZ$4,108
NZ$4,108
NZ$587 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
Showing deals for: 23 Aug - 26 Aug
Kindred Courtyard! Historic Stay w BBQ & Fire Pit
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The current price is NZ$1,485
NZ$1,485
for 3 nights, 1 apartment
NZ$495 per night
includes taxes & fees
Pastor's Cottage in Old Colorado City, luxury getaway with Pikes Peak view!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
The current price is NZ$1,424
NZ$1,424
for 3 nights, 1 home
NZ$475 per night
includes taxes & fees
Baby Blue! Hot Tub! Elegant Kitchen & Bathrooms!
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
The current price is NZ$2,507
NZ$2,507
for 3 nights, 1 home
NZ$836 per night
includes taxes & fees
Shady Grove! 5BR Home w/ Foosball, Walk to OCC!
Sleeps 12 · 5 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
The current price is NZ$2,709
NZ$2,709
for 3 nights, 1 home
NZ$903 per night
includes taxes & fees
Custom Dream Home/ loft&porch/ trendy neighborhood
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
The current price is NZ$2,065
NZ$2,065
for 3 nights, 1 home
NZ$688 per night
includes taxes & fees
🗻Mountain VIEWS!❤️on Colorado Ave!❤️Walkable Neighborhood❤️Backyard❤️Fire Pit🔥
Sleeps 6 · 2 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
The current price is NZ$1,762
NZ$1,762
for 3 nights, 1 home
NZ$587 per night
includes taxes & fees
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