Chalet holiday rentals in Winter Park

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Popular amenities for chalet rentals in Winter Park

Family-friendly chalet rentals

Superhost
Chalet in Breckenridge
4.59 out of 5 average rating, 63 reviews

20 min ski-10 min to Breck-Heated Pool-Hot Tubs

WhitneyRating, 5 stars1 week ago
We absolutely loved our stay at this cozy chalet! It was super cute, clean, and just the right size for our family. The neighborhood felt very safe and peaceful, which meant so much to us with little ones in tow. The chalet backs right up to the national forest, giving us easy access to beautiful hiking trails. Our kids were entertained the whole time with the playground and volleyball area, and the low speed limit (under 10 mph) gave me so much peace of mind as a mom with three young kids riding bikes around. It really felt like a perfect little family getaway spot. We’d definitely stay here again!
Superhost
Chalet in Estes Park
4.69 out of 5 average rating, 32 reviews

Charming One Bedroom Chalet with gas fireplace

LaurenRating, 5 stars9 months ago
Our stay was great. Very close to RMNP so it is extremely convenient and only takes a few minutes to get to the park. Everything was very clean inside
Guest favourite
Chalet in Estes Park
4.95 out of 5 average rating, 77 reviews

Perfect Mountain Getaway #3235 Larimer:20-NCD0416

AndresRating, 5 stars10 months ago
Our stay was wonderful. Erinn was very kind, leaving us eggs from her chickens for us to have breakfast. We recommend this location 100%, very close to restaurants, everywhere in Estes and the parks. Beautiful views, beautiful sunrise with different visits of animals. Thank you Erinn for making our stay very pleasant.
Top guest favourite
Chalet in Vail
5 out of 5 average rating, 62 reviews

Deep Powder Hut - Ski and sun in Vail, CO

DonnaRating, 5 stars3 months ago
The Deep Powder Hut was the perfect home for our family's long weekend birthday celebration in Vail. Each room was beautifully decorated. The beds were so very comfortable. The breathtaking fireplace was a wonderful bonus. Everything you could possibly want/need, and then some, was at your fingertips....right down to the welcome bag of Lindt chocolates. Whenever I had a question Becki was very quick to respond and she was very accommodating.. I wouldn't hesitate to recommend this home to famiIy and friends. We look forward to booking the Deep Powder Hut on our next trip to Vail.
Superhost
Chalet in Vail
4.84 out of 5 average rating, 367 reviews

Vail 3 Brdm/2Ba Charming A-Frame

MalloryRating, 5 stars2 months ago
Quaint spot with great access to the bus line for skiing! It was great to be able to bring our dogs as well. Robert was very accommodating.
Superhost
Chalet in Boulder
4.86 out of 5 average rating, 234 reviews

Stunning Modern Boulder Chalet/Hot Tub/Pool Table

JaneRating, 5 stars5 months ago
My family & I met here for Christmas. The home was so peaceful & quiet, although it was a bit hard to find the first time in the dark. It was worth it! The kids loved the hot tub, & the area had lots of fun things to explore! Thanks, Robert for your part in our great Christmas!
Guest favourite
Chalet in Nederland
4.97 out of 5 average rating, 118 reviews

Secluded Mountain Chalet - Private Shady Trail

VesnaRating, 5 stars1 month ago
A stunning mountain retreat on the top of a hill, with breathtaking views of the surrounding peaks. The home is extra clean, spacious, and feels brand new. The host was incredibly helpful, guiding us throughout our stay and promptly answering all our questions. The experience of being on top of the mountains was truly amazing, with elk roaming freely in the area. Located just 20 minutes from Boulder via a shortcut—be sure to ask the host about it. Highly recommend this place and would definitely stay again.
Chalet in Drake
4.97 out of 5 average rating, 138 reviews

Scenic Solitude near Estes Park/RMNP

JasonRating, 5 stars1 week ago
Easiest review i've ever written... simply the best AirBnB i've ever stayed at!

Luxury chalet rentals

Chalet in Estes Park
4.74 out of 5 average rating, 27 reviews

4BR Rocky Mountain National Park

KaitlinRating, 5 stars4 days ago
Our stay here was great! The house was clean, spacious, and fit our group of 6 very comfortably. Easy to check in and easy to find from the hosts instructions. The location was great, only 10 mins to Rocky Mountain National Park and 10 mins to downtown Estes Park! The only negative was the communication with the host was not very helpful about some small things- when we reached out they said they would get back to us multiple times and never did. Only a minor inconvenience to an otherwise amazing house and stay! Would definitely stay again!
Guest favourite
Chalet in Vail
4.87 out of 5 average rating, 23 reviews

Vail Ski Chalet STR#004113

CaitlinRating, 5 stars5 months ago
Ralph's place is fantastic! It worked out perfectly for my family - we all had plenty of space. The steam shower in the main master bedroom is incredible. The kitchen is great, and plenty of seating options. For skiing - the bus stop is a 5 min walk. All flat. Couldn't have asked for a better spot
Guest favourite
Chalet in Black Hawk
4.95 out of 5 average rating, 44 reviews

Mountain Log Cabin! Lake! Kayak! Hot Tub! Sauna!

MorganRating, 5 stars3 weeks ago
Sarah and Nick’s cabin was so nice! While the weather and the hot tub didn’t exactly cooperate, we had a great time still. The place is gorgeous and peaceful.
Superhost
Chalet in Vail
5 out of 5 average rating, 5 reviews

Intimate 2BR Chalet, Hot Tub, Views! Summer Awaits

AngelinaRating, 5 stars3 months ago
My partner and I had a wonderful, romantic stay here. Would be a great little family get-away too with the extra bedroom. Super cozy, clean, and quiet with nice décor and stunning views. Stargazing from the private hot tub was our favorite part! Only complaint would be low water pressure in the shower. We would definitely stay here again!
Top guest favourite
Chalet in Black Hawk
4.98 out of 5 average rating, 249 reviews

Lakefront • Views • Kayaks • Fishing • HotTub

AdamRating, 5 stars1 week ago
Just wrapped up a three night anniversary stay at this chalet and it was absolutely fantastic. Super clean, incredibly quiet which was exactly what I needed, and right on the lake. The hot tub on the deck overlooking the lake was just awesome. The house had pretty much any amenity you can think of including things I didn’t necessarily expect like the lanterns, awesome blue tooth speaker, and the gift that was left for us. I’ve stayed in quite a few AirBnb’s but this one is definitely up there as one of my favorites. The host was incredibly responsive and great at communicating which made the stay even more enjoyable. I highly highly recommend this place for anyone looking to get away in the mountains. You won’t be disappointed!
Chalet in Vail

1BR Ski In/Out Mountainview | Pool | Hot Tub

Quick stats about chalet rentals in Winter Park

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹33,673 before taxes and fees

  • Total number of reviews

    160 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Colorado
  4. Grand County
  5. Winter Park
  6. Chalet rentals