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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Winter Park chalets

Exterior

Peaceful Mountain Chalet with gorgeous views!

Peaceful Mountain Chalet with gorgeous views!
Black Hawk
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful views, really enjoyed the stay"
United States
Vlad L.
The price is AED 580
AED 1,456 total
includes taxes & fees
1 Jun - 2 Jun
Peaceful Mountain Chalet with gorgeous views!
Terrace/patio

Sun & Snow Chalet Breckenridge, a Dog Lovers Dream

Sun & Snow Chalet Breckenridge, a Dog Lovers Dream
Northside Breck
9.2 out of 10, Wonderful, (30 reviews)
"Good, clean place!"
United States
Paul B.
The price is AED 551
AED 1,371 total
includes taxes & fees
31 May - 1 Jun
Sun & Snow Chalet Breckenridge, a Dog Lovers Dream
Property grounds

2BR Riverside Chalet, Near Trails

2BR Riverside Chalet, Near Trails
Northside Breck
9.8 out of 10, Exceptional, (25 reviews)
"Great property! Beautiful setting. "
United States
Dan F.
The price is AED 411
AED 1,377 total
includes taxes & fees
31 May - 1 Jun
2BR Riverside Chalet, Near Trails
Exterior

Tranquility Executive Chalet

Tranquility Executive Chalet
Northside Breck
10.0 out of 10, Exceptional, (1 review)
"Perfect little cabin, perfect location. Will definitely stay here again! "
United States
Danny D.
The price is AED 635
AED 1,507 total
includes taxes & fees
31 May - 1 Jun
Tranquility Executive Chalet
Exterior detail

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

Breckenridge Tiger Run Resort. 6 Minutes to the Gondola - Free Shuttle on Hwy 9
Northside Breck
9.2 out of 10, Wonderful, (122 reviews)
"The host was very welcomeing, we enjoyed our stay."
United States
Allen D.
The price is AED 612
AED 1,260 total
includes taxes & fees
31 May - 1 Jun
Breckenridge Tiger Run Resort. 6 Minutes to the Gondola - Free Shuttle on Hwy 9
Exterior

Luxe Summer Chalet: Epic Lake Views, Cinema & Gym - 8 Min to RMNP + Hot Tub

Luxe Summer Chalet: Epic Lake Views, Cinema & Gym - 8 Min to RMNP + Hot Tub
Grand Lake
10.0 out of 10, Exceptional, (6 reviews)
"Great stay at Rocky Mountain Hideaway. Host were accommodating and views were unmatched. "
United States
JJ R.
The price is AED 1,782
AED 4,303 total
includes taxes & fees
1 Jun - 2 Jun
Luxe Summer Chalet: Epic Lake Views, Cinema & Gym - 8 Min to RMNP + Hot Tub
Exterior

Modern Mountain Escape | Hot Tub & Fireplace

Modern Mountain Escape | Hot Tub & Fireplace
Winter Park Highlands
9.2 out of 10, Wonderful, (5 reviews)
"Such an amazing stay! Modern home with stunning mountain views, super clean, and the hot tub was perfect after a long day. Hosts were great and easy to communicate with. Highly recommend!"
United States
Rachel S.
The price is AED 2,173
AED 4,309 total
includes taxes & fees
31 May - 1 Jun
Modern Mountain Escape | Hot Tub & Fireplace
Chalet, 3 Bedrooms | Exterior

Mountain Vista 3 Bedroom Chalet by RedAwning

Mountain Vista 3 Bedroom Chalet by RedAwning
3.0 star property
Winter Park Highlands
The price is AED 2,054
AED 6,165 total
includes taxes & fees
1 Jun - 2 Jun
Mountain Vista 3 Bedroom Chalet by RedAwning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Park Hotel Reviews

CLEAN, PET-FREE, MOUNTAIN VIEW, SPACIOUS KITCHEN- steps from village of WP!

CLEAN, PET-FREE, MOUNTAIN VIEW, SPACIOUS KITCHEN- steps from village of WP!

10/10 Excellent
"This is an excellent choice for a family staying in Winter Park. The only reason the cleanliness rating took a hit was because the host had a miscommunication with their cleaning crew, who cleaned the wrong condo the day before we arrived. Once we checked in and found it not ready for our arrival, she had them there within minutes, and by the time we got back from lunch, it was spotless and ready for our stay.The location is terrific, right next to an outdoor concert venue and walking distance from the shops and restaurants, as well as a short 5-minute drive from some pleasant hiking trails above the town.This is perhaps the most organized and well-marked place we’ve stayed, everything labeled and easy to find. The balcony has an excellent mountain view, and the pool/hot tub are right across the parking lot.We didn’t need them on Memorial Day Weekend, but the radiant heating in the floors would be pretty clutch in the winter time I’m sure. Great thoughtfulness reflected in that addition.Overall a terrific stay and would definitely make this a first look if we return back to Winter Park!"
David B. 3-night trip
Posted 5 days ago
CLEAN, PET-FREE, MOUNTAIN VIEW, SPACIOUS KITCHEN- steps from village of WP!