Photo by Ryan Carlos
Westside holiday homes
We found 242 holiday rentals — enter your dates for availability
Discover a selection of 96 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:17 Oct - 24 Oct
Image gallery for Tiger Lair! Near Colorado College & Robson Arena
9.29.2 out of 10 rating
Wonderful
(32 reviews)
Tiger Lair! Near Colorado College & Robson Arena
Colorado Springs, Colorado
5% off
Price is NZ$3,218
NZ$3,218
NZ$460 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$4,304
NZ$4,304
NZ$615 per night
includes taxes & fees
Image gallery for 3BD Family Vacation Home Near Hiking & Downtown
1010 out of 10 rating
Exceptional
(5 reviews)
3BD Family Vacation Home Near Hiking & Downtown
Colorado Springs, Colorado
7% off
Price is NZ$3,070
NZ$3,070
NZ$439 per night
includes taxes & fees
Image gallery for Vibrant Watermelon! Hot Tub & King Bed & BBQ!
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Vibrant Watermelon! Hot Tub & King Bed & BBQ!
Colorado Springs, Colorado
5% off
Price is NZ$2,513
NZ$2,513
NZ$359 per night
includes taxes & fees
Image gallery for Charming Downtown Cottage with Parking & Full Kitchen
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Charming Downtown Cottage with Parking & Full Kitchen
Colorado Springs, CO
7% off
Price is NZ$1,154
NZ$1,154
NZ$165 per night
includes taxes & fees
Image gallery for Highland Heights! Luxe Mountain VIEWS w/ Hot Tub
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Highland Heights! Luxe Mountain VIEWS w/ Hot Tub
Colorado Springs, Colorado
6% off
Price is NZ$13,096
NZ$13,096
NZ$1,871 per night
includes taxes & fees
Image gallery for Two Bedroom Home in the Heart of West Colorado Springs
9.89.8 out of 10 rating
Exceptional
(172 reviews)
Two Bedroom Home in the Heart of West Colorado Springs
Colorado Springs, CO
8% off
Price is NZ$1,909
NZ$1,909
NZ$273 per night
includes taxes & fees
Image gallery for 2BR Old Colorado City Dog Friendly!
9.29.2 out of 10 rating
Wonderful
(15 reviews)
2BR Old Colorado City Dog Friendly!
Colorado Springs, Colorado
7% off
Price is NZ$2,514
NZ$2,514
NZ$359 per night
includes taxes & fees
Image gallery for Close to attractions with mountain views. Walk to restaurants and shops in OCC!
9.89.8 out of 10 rating
Exceptional
(102 reviews)
Close to attractions with mountain views. Walk to restaurants and shops in OCC!
Colorado Springs, CO
8% off
Price is NZ$5,035
NZ$5,035
NZ$719 per night
includes taxes & fees
Image gallery for Newly Remodeled Pet Friendly Cottage
8.68.6 out of 10 rating
Excellent
(98 reviews)
Newly Remodeled Pet Friendly Cottage
Colorado Springs, CO
7% off
Price is NZ$1,279
NZ$1,279
NZ$183 per night
includes taxes & fees
Image gallery for Game Parlour! Downtown Workspace BBQ Fire Pit
8.68.6 out of 10 rating
Excellent
(9 reviews)
Game Parlour! Downtown Workspace BBQ Fire Pit
Colorado Springs, Colorado
5% off
Price is NZ$2,168
NZ$2,168
NZ$310 per night
includes taxes & fees
Image gallery for Baby Blue! Hot Tub! Elegant Kitchen & Bathrooms!
9.49.4 out of 10 rating
Exceptional
(28 reviews)
Baby Blue! Hot Tub! Elegant Kitchen & Bathrooms!
Colorado Springs, Colorado
6% off
Price is NZ$3,684
NZ$3,684
NZ$526 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$2,749
NZ$2,749
NZ$393 per night
includes taxes & fees
Image gallery for Cheerful 3-bedroom minutes from downtown and OCC
1010 out of 10 rating
Exceptional
(30 reviews)
Cheerful 3-bedroom minutes from downtown and OCC
Colorado Springs, CO
16% off
Price is NZ$1,828
NZ$1,828
NZ$261 per night
includes taxes & fees
Image gallery for Old Colorado City Get Away
9.09.0 out of 10 rating
Wonderful
(35 reviews)
Old Colorado City Get Away
Colorado Springs, CO
8% off
Price is NZ$1,682
NZ$1,682
NZ$240 per night
includes taxes & fees
Image gallery for Trail Climb! Downtown Home w BBQ & Scenic Views!
9.09.0 out of 10 rating
Wonderful
(22 reviews)
Trail Climb! Downtown Home w BBQ & Scenic Views!
Colorado Springs, Colorado
5% off
Price is NZ$2,938
NZ$2,938
NZ$420 per night
includes taxes & fees
Image gallery for Miners Anvil! Steps to Historic District & OCC
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Miners Anvil! Steps to Historic District & OCC
Colorado Springs, Colorado
5% off
Price is NZ$1,886
NZ$1,886
NZ$269 per night
includes taxes & fees
Image gallery for Cozy home near downtown Colorado Springs and Old Colorado City
9.89.8 out of 10 rating
Exceptional
(66 reviews)
Cozy home near downtown Colorado Springs and Old Colorado City
Colorado Springs, CO
7% off
Price is NZ$1,789
NZ$1,789
NZ$256 per night
includes taxes & fees
Image gallery for The General Store- Private and centrally located
9.69.6 out of 10 rating
Exceptional
(7 reviews)
The General Store- Private and centrally located
Colorado Springs, CO
7% off
Price is NZ$2,195
NZ$2,195
NZ$314 per night
includes taxes & fees
Image gallery for Crescent Estate! Mtn Views, Walk DT, Golf, Hot Tub
8.88.8 out of 10 rating
Excellent
(8 reviews)
Crescent Estate! Mtn Views, Walk DT, Golf, Hot Tub
Colorado Springs, Colorado
6% off
Price is NZ$11,004
NZ$11,004
NZ$1,572 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$4,613
NZ$4,613
NZ$659 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
7% off
Price is NZ$4,460
NZ$4,460
NZ$637 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$3,044
NZ$3,044
NZ$435 per night
includes taxes & fees
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$6,017
NZ$6,017
NZ$860 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Westside
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
120 reviews(120 reviews)
Baby Blue! Hot Tub! Elegant Kitchen & Bathrooms!
Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Kindred Courtyard! Historic Stay w BBQ & Fire Pit
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
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)
🗻Mountain VIEWS!❤️on Colorado Ave!❤️Walkable Neighborhood❤️Backyard❤️Fire Pit🔥
Sleeps 6 · 2 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
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)
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