Vacations in Winter Park

Vacations in Winter Park

2 travelers

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Cheap Winter Park package deals

These are the best prices for May 23 - 26.
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BreakfastHalf boardSelf cateringAll inclusiveMeals not included

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$439 - $944$944 - $1,449$1,449 - $1,954$1,954 - $2,459$2,459+ per night

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Most popular Winter Park flight and hotel deals

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Select Unit 1710 - 2BR - Zephyr Mountain Lodge condo - Winter Park - Kitchen
Select Unit 1710 - 2BR - Zephyr Mountain Lodge condo - Winter Park - Kitchen
Select Unit 1710 - 2BR - Zephyr Mountain Lodge condo
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$866
Ski Slope View Remodeled Zephyr Mountain Lodge Condo condo - Winter Park - Kitchen
Ski Slope View Remodeled Zephyr Mountain Lodge Condo condo - Winter Park - Kitchen
Ski Slope View Remodeled Zephyr Mountain Lodge Condo condo
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$833
One-Bedroom Apartment - Winter Park - Living room
One-Bedroom Apartment - Winter Park - Living room
One-Bedroom Apartment
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$711
Fraser Crossing/Founders Pointe, Condo | Top Floor Ski-In/Ski-Out (Premium-Rated Condo 3622) - Winter Park - Balcony
Fraser Crossing/Founders Pointe, Condo | Top Floor Ski-In/Ski-Out (Premium-Rated Condo 3622) - Winter Park - Balcony
Fraser Crossing/Founders Pointe, Condo | Top Floor Ski-In/Ski-Out (Premium-Rated Condo 3622)
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$572
Charming Fraser Crossing Founders Pointe - Winter Park - Balcony
Charming Fraser Crossing Founders Pointe - Winter Park - Balcony
Charming Fraser Crossing Founders Pointe
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$668
Base Camp At Iron Horse 4 Bedroom Townhouse by RedAwning - Winter Park - Building
Base Camp At Iron Horse 4 Bedroom Townhouse by RedAwning - Winter Park - Building
Base Camp At Iron Horse 4 Bedroom Townhouse by RedAwning
10 Wonderful
Kansas City
Meals not included
3 nights + flight
$2,404
Founders - 4374 2 Bedroom Condo by RedAwning - Winter Park - Balcony
Founders - 4374 2 Bedroom Condo by RedAwning - Winter Park - Balcony
Founders - 4374 2 Bedroom Condo by RedAwning
Kansas City
Meals not included
3 nights + flight
$1,002
Zephyr Mountain Lodge, Condo , 2 bedroom (Premium-Rated Condo 1506) - Winter Park - Bedroom
Zephyr Mountain Lodge, Condo , 2 bedroom (Premium-Rated Condo 1506) - Winter Park - Bedroom
Zephyr Mountain Lodge, Condo , 2 bedroom (Premium-Rated Condo 1506)
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$758
Premium Unit 2308 - 1Br - Zephyr Mountain Lodge condo - Winter Park - Living room
Premium Unit 2308 - 1Br - Zephyr Mountain Lodge condo - Winter Park - Living room
Premium Unit 2308 - 1Br - Zephyr Mountain Lodge condo
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$594
Zephyr Mountain Lodge, Condo | 2 Bedroom (Value-Rated Condo 1607) - Winter Park - Bedroom
Zephyr Mountain Lodge, Condo | 2 Bedroom (Value-Rated Condo 1607) - Winter Park - Bedroom
Zephyr Mountain Lodge, Condo | 2 Bedroom (Value-Rated Condo 1607)
10 Wonderful
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$715
Comfortable Fraser Crossing Founders Pointe Condo Near Gondola with Onsite Ski Storage condo - Winter Park - Living room
Comfortable Fraser Crossing Founders Pointe Condo Near Gondola with Onsite Ski Storage condo - Winter Park - Living room
Comfortable Fraser Crossing Founders Pointe Condo Near Gondola with Onsite Ski Storage condo
10 Wonderful
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$808
Stunning Zephyr Mountain Lodge Condo Overlooking The Village Plaza condo - Winter Park - Living room
Stunning Zephyr Mountain Lodge Condo Overlooking The Village Plaza condo - Winter Park - Living room
Stunning Zephyr Mountain Lodge Condo Overlooking The Village Plaza condo
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$687
Premium Unit 2216 - 1 Br - Zephyr Mountain Lodge condo - Winter Park - Bedroom
Premium Unit 2216 - 1 Br - Zephyr Mountain Lodge condo - Winter Park - Bedroom
Premium Unit 2216 - 1 Br - Zephyr Mountain Lodge condo
10 Wonderful
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$711
Lovely Zephyr Mountain Lodge Condo With - Winter Park - Balcony
Lovely Zephyr Mountain Lodge Condo With - Winter Park - Balcony
Lovely Zephyr Mountain Lodge Condo With
8.7 Very good
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$728
Two-Bedroom Apartment - Winter Park
Two-Bedroom Apartment - Winter Park
Two-Bedroom Apartment
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$758
Value Unit 1422 - 2BR - Zephyr Mountain Lodge condo - Winter Park - Bedroom
Value Unit 1422 - 2BR - Zephyr Mountain Lodge condo - Winter Park - Bedroom
Value Unit 1422 - 2BR - Zephyr Mountain Lodge condo
10 Wonderful
Free Wi-Fi
Kansas City
Meals not included
3 nights + flight
$840

When to book a vacation in Winter Park

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Tips for finding Winter Park package deals

  • There are loads of types of vacations in Winter Park and the cost will depend on what type of trip you’re taking and for how long you’d like to stay. Here are the latest prices for a 3 night trip for 2 travelers: Top vacation $22; Family vacation $106; Romantic vacation $112; Budget vacation $177.

Where to stay in Winter Park

Our map will help you find the perfect place to stay for your vacation in Winter Park by showing you the exact location of each hotel.

Everything you need to know for your vacation in Winter Park

Winter Park vacation information

Top vacation (Flight+Hotel)$22
Family vacation (Flight+Hotel)$106
Romantic vacation (Flight+Hotel)$112
Budget vacation (Flight+Hotel)$177