Winter Park Chalets

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Our top choices for Winter Park chalets

A wooden deck with two wooden chairs and a table, a blanket, and two cups on the table.

1. Cozy Rocky Mnt. Chalet/Spa, private lake, close to Denver, RedRocks, Outdoor fun

Idaho Springs

Vince A.

includes taxes & fees

27 Oct - 28 Oct

A modern two-story house with a balcony, a garage, and a stone facade.

2. Peaceful Mountain Chalet with gorgeous views!

Black Hawk

Debbie

includes taxes & fees

26 Oct - 27 Oct

A wooden cabin with a deck overlooking a snow-covered landscape and a clear stream.

3. 2BR Riverside Chalet, Near Trails

Northside Breck

Dan F.

includes taxes & fees

25 Oct - 26 Oct

A rustic cabin with a stone foundation, surrounded by trees, overlooking a lake and mountains.

4. Luxury / 3 Kings, Hot Tub, Lake Views, 4K Theater, Arcade + Gym / 8 Min RMNP

Grand Lake

Amber S.

A deck with lounge chairs and a railing, surrounded by tall pine trees and a mountain in the background.

5. Shadow Mountain Chalet • Lake Views • Hot Tub • Sauna • Family Friendly

Grand Lake

Matthew S.

includes taxes & fees

23 Oct - 24 Oct

A wooden deck with a rocking chair and a small table, overlooking a green landscape and a cabin.

6. Sun & Snow Chalet Breckenridge, a Dog Lovers Dream

Northside Breck

Matthew

A cozy living room with a wooden ceiling, a sofa, a coffee table, and a vase of flowers.

7. Breckenridge Tiger Run Resort. 6 Minutes to the Gondola - Free Shuttle on Hwy 9

Northside Breck

Allen D.

includes taxes & fees

23 Oct - 24 Oct

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Top Winter Park Hotel Reviews

The Vintage Hotel

10/10 Excellent

"McKenzie and the team are on point when we arrive, the staff is friendly and always welcoming. They are pet friendly with a small fee, but every penny worth it for our pup. Stayed 3 weekends in a row and everytime was the absolute best."

Fraser Crossing Founders Pointe

10/10 Excellent

"This is the 2nd time we have stayed here but the first to come in October in between seasons. We loved it even though everything was closed across the street in the village. We liked the quiet and less people. The jacuzzi is large and fabulous…one of our favorite things about this property. The got a studio this time….the bed was comfortable and we liked having a couch to sit on to watch tv. The water pressure was low but we dealt with it. Close to town with great restaurants. Took Corona Pass all the way to the top of Rollins Pass and enjoyed the beautiful view. We love staying here and will be back of course."

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

10/10 Excellent

"The best place to stay in Winter Park! The location is great, the property is beautiful and the host is the best! Very responsive when I had a “senior moment” and couldn’t find my check-in instructions. Hated to leave, will definitely be back"

Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22

10/10 Excellent

"Fantastic location right by a creek. The house was clean and well organized with some fun games like ping pong & pool as well. Also, walkable to the winterpark town!Our group really enjoyed our stay here. House manager was also great & prompt in resolving, when we had a hot tub issue. Overall, highly recommend."

Renovated Condo near the Slopes and Trails

8/10 Good

"Clean and convenient location. More than adequate for our needs, though the plastic mattress covers in the bunk room were not ideal. Cumbersome approach to 2nd floor up slightly sloped stairs and a door that opens to the unit on the wrong side. Current renovations are lovely…keep going!"

Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...

10/10 Excellent

"The location was great. The house was very clean. The amenities were great from the towels for the hot tub to the well-equipped kitchen. We were a party of 10 and we ate most of our meals because it was comfortable, fun and easy to accommodate all the cooks in the kitchen. We did Elevation Everest, lots of Downhill MTB and hikes. If we ever come back to Winter Park, we will surely stay here again. I forgot my Dyson hairdryer and I’m sure Bob is shipping it back to me now."

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