Photo by Ryan Carlos
Westside holiday homes
We found 236 holiday rentals — enter your dates for availability
Discover a selection of 95 homes, 29 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:19 Sept - 26 Sept
Image gallery for Family-friendly with stunning views & great yard
1010 out of 10 rating
Exceptional
(139 reviews)
Family-friendly with stunning views & great yard
Colorado Springs, CO
13% off
Price is NZ$4,999
NZ$4,999
NZ$714 per night
includes taxes & fees
Image gallery for Highland Heights! Hot Tub, BBQ & Mountain Views
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Highland Heights! Hot Tub, BBQ & Mountain Views
Colorado Springs, Colorado
6% off
Price is NZ$18,236
NZ$18,236
NZ$2,605 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$3,196
NZ$3,196
NZ$457 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$2,219
NZ$2,219
NZ$317 per night
includes taxes & fees
Image gallery for Cozy New Home with King Suite & Hot Tub Near Garden of the Gods!
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Cozy New Home with King Suite & Hot Tub Near Garden of the Gods!
Colorado Springs, CO
17% off
Price is NZ$3,806
NZ$3,806
NZ$544 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$5,570
NZ$5,570
NZ$796 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
7% off
Price is NZ$3,185
NZ$3,185
NZ$455 per night
includes taxes & fees
Image gallery for Westside Stairway to a Haven in Old Colorado City at the base of Pikes Peak
1010 out of 10 rating
Exceptional
(6 reviews)
Westside Stairway to a Haven in Old Colorado City at the base of Pikes Peak
Colorado Springs, CO
12% off
Price is NZ$1,811
NZ$1,811
NZ$259 per night
includes taxes & fees
Image gallery for Peak Pool Hall! Billiards Room & BBQ & Fire Pit!
8.68.6 out of 10 rating
Excellent
(10 reviews)
Peak Pool Hall! Billiards Room & BBQ & Fire Pit!
Colorado Springs, Colorado
6% off
Price is NZ$3,182
NZ$3,182
NZ$455 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$2,192
NZ$2,192
NZ$313 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$5,743
NZ$5,743
NZ$820 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
7% off
Price is NZ$4,215
NZ$4,215
NZ$602 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
(73 reviews)
Pet Friendly Cottage located between Old Colorado City and Downtown!
Colorado Springs, CO
6% off
Price is NZ$1,997
NZ$1,997
NZ$285 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$2,342
NZ$2,342
NZ$335 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$2,784
NZ$2,784
NZ$398 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$3,803
NZ$3,803
NZ$543 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$3,518
NZ$3,518
NZ$503 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$2,766
NZ$2,766
NZ$395 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$5,480
NZ$5,480
NZ$783 per night
includes taxes & fees
Image gallery for Miners Anvil! Steps to Historic District & OCC
1010 out of 10 rating
Exceptional
(5 reviews)
Miners Anvil! Steps to Historic District & OCC
Colorado Springs, Colorado
6% off
Price is NZ$2,916
NZ$2,916
NZ$417 per night
includes taxes & fees
Image gallery for Colorado Cottage! Downtown, OCC w Patio!
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Colorado Cottage! Downtown, OCC w Patio!
Colorado Springs, Colorado
6% off
Price is NZ$2,774
NZ$2,774
NZ$396 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
5% off
Price is NZ$1,627
NZ$1,627
NZ$232 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
(160 reviews)
Hot Tub! Walk to Historic Old Colorado City & Shops.
Colorado Springs, CO
8% off
Price is NZ$2,874
NZ$2,874
NZ$411 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$4,209
NZ$4,209
NZ$601 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: 14 Sept - 17 Sept
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
117 reviews(117 reviews)
The current price is NZ$1,416
NZ$1,416
for 3 nights, 1 home
NZ$472 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$2,087
NZ$2,087
for 3 nights, 1 home
NZ$696 per night
includes taxes & fees
Cozy & Remodeled Steps to Downtown & OCC w/firepit
Sleeps 4 · 2 bedrooms · 1 bathroom
8.88.8 out of 10
Excellentexcellent
5 reviews(5 reviews)
The current price is NZ$1,337
NZ$1,337
for 3 nights, 1 home
NZ$446 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$1,756
NZ$1,756
for 3 nights, 1 home
NZ$585 per night
includes taxes & fees
Peak Pool Hall! Billiards Room & BBQ & Fire Pit!
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
10 reviews(10 reviews)
The current price is NZ$1,634
NZ$1,634
for 3 nights, 1 home
NZ$545 per night
includes taxes & fees
Designer Retreat | walk to brewery & cafés
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
The current price is NZ$1,226
NZ$1,226
for 3 nights, 1 home
NZ$409 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