Holiday rentals in Bailey

4.95 out of 5 average rating, 201 reviews

Cabin in Winter Park

Cozy Log Home,Sleeps 10. Free shuttle,3 min-slopes

DanyaRating, 5 stars1 month ago

Sherri was the ultimate hostess with the mostest, the goddess of winter park. She went above and beyond to make sure we had an awesome stay, including helping us find childcare for our 3 kids. The house is perfect for young families. Lots of toys and room to play. Beds are super comfy. Kitchen is fully equipped. The house is right on the bus line so skiing is super close. We will definitely stay again!

4.97 out of 5 average rating, 152 reviews

Home in Leadville

Matchless Mountain Lodge, Hot Tub, Mtn. Views

BeccaRating, 5 stars2 weeks ago

We absolutely loved our stay at this charming house in Leadville! From the moment we walked in, it was clear how much care and attention had gone into making this place special. The home was spotless, beautifully decorated, and full of cozy touches that made it feel like a home away from home. The location was perfect—just minutes from downtown but still tucked away enough to feel peaceful and private. We especially loved waking up to the mountain views and sipping coffee on the porch in the crisp morning air. Every amenity we could’ve needed was thoughtfully provided, from a well-stocked kitchen to comfy beds and extra blankets. The hosts were incredibly kind and responsive, making check-in a breeze and offering great local tips. Whether you’re visiting for skiing, hiking, or just a quiet getaway, this place is an absolute treasure. We can't wait to go back!

4.87 out of 5 average rating, 404 reviews

Home in Colorado Springs

✵ Downtown Couples Retreat in the hip North End ✵

AndreaRating, 5 stars2 days ago

This was a lovely stay! the house is super cute and they have found ways to allow good air flow and the bed is very comfortable and welcoming. The host was very helpful in responsive to our concerns and needs.

4.91 out of 5 average rating, 429 reviews

Home in Colorado Springs

5BR Retreat w/ Hot Tub, Gym, & Cheyenne Mtn Views!

MichaelRating, 5 stars1 day ago

This is our groups second time staying with Zoltan. This is the second of his properties we have stayed at and both places were outstanding, with a great host! Excellent communication and extremely friendly. I HIGHLY recommend anyone in the area with a large group, contact Zoltan and treat yourself to one of his locations. Can’t wait for next years trip and will absolutely be looking forward to staying with this host again!

4.92 out of 5 average rating, 124 reviews

Home in Leadville

Like New Leadville Mountain House/Cabin

AmyRating, 5 stars1 month ago

We loved our stay here! It was perfect for our family of 5. All three of our kids had their own bed, which was really nice. The kitchen was very well stocked with everything you could need and the place was spotlessly clean. The house is very cozy and the gas fireplace in the living room is so easy to use and wonderful after being outside in the cold all day skiing. Richard was very proactive and helpful in his communications and it was so easy getting into the house. This location worked out great for our week in Leadville skiing at Ski Cooper. Highly recommend.

Apartment in Breckenridge

4.91 out of 5 average rating, 233 reviews

True ski in/out. Upscale modern rustic

JohnRating, 5 stars1 month ago

We had a great stay at Jen’s condo. Walk less than 100 yds to the Snowflake lift. At the end of the day, ski home on the 4 o’clock trail and step off the trail into the parking lot for the condo. Very comfortable for 2 people, well-appointed kitchen, and easy walk into town. Highly recommended

4.85 out of 5 average rating, 46 reviews

Townhouse in Dillon

Discounted rates to enjoy remaining ski days!

AlejandraRating, 5 stars2 months ago

The townhome was very spacious and clean. The location is great with a lot of restaurants and breweries nearby. Cami was very responsive and easy to get a hold of. Our only feedback is that the bed in the primary bedroom was very uncomfortable and should be updated. Overall, we enjoyed our stay here.

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Kick off your hiking boots at these rustic lodgings

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Popular amenities for Bailey holiday rentals

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Pool

Free parking on premises

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Stay near Bailey's top sights

Staunton State Park107 locals recommend

Aspen Peak Cellars49 locals recommend

Mad Jack's Mountain Brewery43 locals recommend

The Shaggy Sheep41 locals recommend

Cut Throat Cafe40 locals recommend

Sasquatch Outpost36 locals recommend

Other great holiday rentals in Bailey

4.9 out of 5 average rating, 112 reviews

Home in Frisco

Walk to Main St: Frisco Home w/ Hot Tub & Deck!

NicoleRating, 5 stars1 month ago

The house was lovely and the location was fantastic - walkable to the adorable downtown of Frisco. Hosts were very responsive to any questions we had.

Apartment in Breckenridge

4.89 out of 5 average rating, 345 reviews

Stunning Views - Downtown - Base of Peak Nine

KathrynRating, 5 stars2 weeks ago

Peak 9's lift was closed but the bus to get us to Peak 8 was right outside. We were able to end the day riding all the back to the village which was awesome. The amenities were lovely and you cannot beat the location!

Guest house in Buena Vista

4.92 out of 5 average rating, 215 reviews

Dawn & J's Stay and Play - STR-089

MattRating, 5 stars1 month ago

I generally rent another airbnb in BV, but changed it up for this visit. And I was extremely pleased! Beautiful, spacious & peaceful rental that was a great value to enjoy all things in BV and the surrounding area. I loved the balcony that faced west for quiet mornings, sunny afternoons & stargazing at nite. Very responsive hosts. I look forward to my next stay. I know you will too!

4.83 out of 5 average rating, 132 reviews

Loft in Granby

Ski in/out- Sleeps 8 Granby Ranch Mountainside #69

BenjaminRating, 5 stars3 months ago

super pleased with our stay. layout was great for us as the kids room was adjacent to ours👍👍

5 out of 5 average rating, 22 reviews

Home in Colorado Springs

Relaxing Home away from home, 7 BR/8 Beds/Sleeps14

ChrystalRating, 5 stars4 months ago

Kevin’s home is beautiful the pictures do it no justice. Kevin is an accommodating host and very responsive. We enjoyed our stay so much that we plan to use the home again. The entire home was clean and spacious. I really felt at home.

5 out of 5 average rating, 94 reviews

Home in Breckenridge

Luxury Private Home In A Great Location. Hot Tub.

KevinRating, 5 stars2 weeks ago

Great location with lots of room. The views were excellent and the living room was large enough for all the people me we had. Another great feature was how many bathrooms there were. Made it super nice with over 5 people in one house. We would stay here again for sure, great stay!

Apartment in Silverthorne

4.8 out of 5 average rating, 151 reviews

Newly Renovated Silverthorne Vacation Condo

SergeyRating, 5 stars2 weeks ago

It was very quiet and very close to ski areas