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Winter Park Vacation Rentals

Find 3,379 available offers from 8 partners
Winter Park
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Condo
Cabin
House
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

Ski the slopes and savor superb views with Winter Park vacation homes

Spacious cabin rentals and modern condo vacation rentals in Winter Park put you near all the action on the ski resort's mountainside. Enjoy the woodsy locale and proximity to Colorado's scenic nature.

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Best Vacation Home Deals in Winter Park

Save up to 57%

House Winter Park
Apr 19 - Apr 26
-50%
$800
$400 per night
House ∙ 12 guests ∙ 4 bedrooms
Vacation Home in Winter Park with Grill
4.9
Outstanding (88 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
May 3 - May 10
-34%
$209
$138 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Winter Park with Scenic Balcony
4.6
Excellent (11 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Oct 6 - Oct 13
-57%
$238
$104 per night
House ∙ 8 guests ∙ 3 bedrooms
Wonderful House in Fraser with Jacuzzi & Grill
4.5
Excellent
Winter Park, Grand County, Colorado, United States
Details
Vacasa
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Compare and find a vacation rental that fits your needs among the 3,379 fantastic rentals from several partner websites in Winter Park. Every one of the offers from our partner websites are instantaneously compared on our website , allowing you to save up to 56%.

Top-Rated Rentals and Accommodations in Winter Park

Book Vacation Rental Offers with the Highest User Rating

House Winter Park
Oct 16 - Oct 23
$395 per night
House ∙ 12 guests ∙ 4 bedrooms
Vacation Home in Winter Park with Grill + Mountain View
5.0
Outstanding (102 ratings)
Winter Park, Grand County, Colorado, United States
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Condo Winter Park
Oct 20 - Oct 27
-41%
$537
$319 per night
Condo ∙ 16 guests ∙ 1 bedroom
Wonderful Condo in Fraser with Grill + Beautiful Views
4.9
Outstanding (17 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Nov 3 - Nov 10
-46%
$349
$187 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Winter Park with Electric Fireplace + Vast Views
5.0
Outstanding (8 ratings)
Winter Park, Grand County, Colorado, United States
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Recommended Vacation Rentals in Winter Park

Find your perfect vacation rental in Winter Park: from $47 per night

House Winter Park
Oct 20 - Oct 27
-49%
$273
$141 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Fraser with Free Parking + Valley View
5.0
Outstanding (11 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Nov 11 - Nov 18
-82%
$764
$141 per night
House ∙ 9 guests ∙ 4 bedrooms
Vacation Home in Granby with Free Parking + Incredible Views
4.9
Outstanding (26 ratings)
Winter Park, Grand County, Colorado, United States
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Condo Winter Park
Oct 21 - Oct 28
-74%
$318
$83 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Winter Park with Unassigned Parking
4.8
Outstanding (18 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Oct 6 - Oct 13
-87%
$770
$104 per night
House ∙ 10 guests ∙ 2 bedrooms
Vacation Home in Fraser + Mountain Views
4.9
Outstanding (14 ratings)
Winter Park, Grand County, Colorado, United States
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Condo Winter Park
Oct 2 - Oct 9
-66%
$322
$109 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Granby with Ground-Floor Patio + Incredible Views
5.0
Outstanding (55 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Oct 6 - Oct 13
-77%
$502
$116 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in Granby with Grill + Pastoral Views
4.4
Very good (24 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Oct 2 - Oct 9
-75%
$542
$137 per night
House ∙ 10 guests ∙ 3 bedrooms
Beautiful House in Granby with Jacuzzi & Grill + Unobstructed Views
4.5
Excellent (36 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
May 18 - May 25
-21%
$595
$468 per night
House ∙ 23 guests ∙ 6 bedrooms
Vacation Home in Fraser with Grill & Yard
4.9
Outstanding (132 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Jun 15 - Jun 22
-31%
$758
$525 per night
House ∙ 16 guests ∙ 6 bedrooms
Vacation Home in Fraser with Grill
4.9
Outstanding (160 ratings)
Winter Park, Grand County, Colorado, United States
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Budget-friendly Vacation Rentals in Winter Park

Find Fantastic yet Inexpensive Offers

Condo Winter Park
Sep 21 - Sep 28
-79%
$473
$98 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Winter Park with Private Balcony + Picturesque View
4.7
Excellent (3 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Nov 4 - Nov 11
-52%
$596
$287 per night
House ∙ 11 guests ∙ 4 bedrooms
Vacation Home in Winter Park with Grill
5.0
Outstanding (13 ratings)
Winter Park, Grand County, Colorado, United States
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Condo Winter Park
Oct 13 - Oct 20
-77%
$489
$112 per night
Condo ∙ 6 guests ∙ 1 bedroom
Condo in Winter Park with Grill
5.0
Outstanding (4 ratings)
Winter Park, Grand County, Colorado, United States
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Winter Park rental with full kitchen.

House  Winter Park
Nov 4 - Nov 11
-33%
$307
$206 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in Winter Park with Grill + Valley Views
4.8
Outstanding (10 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
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Condo  Winter Park
Oct 7 - Oct 14
-54%
$167
$77 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Winter Park with Indoor-Outdoor Pool
4.6
Excellent (137 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
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House  Winter Park
Nov 3 - Nov 10
$364 per night
House ∙ 10 guests ∙ 3 bedrooms
Charming House in Fraser with Grill & Pool
5.0
Outstanding (45 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Winter Park accommodation with high-speed internet.

House  Winter Park
Oct 20 - Oct 27
-39%
$900
$550 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Fraser with Grill + Fabulous Views
4.8
Outstanding (42 ratings)
Winter Park, Grand County, Colorado, United States
Internet
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House  Winter Park
Jun 15 - Jun 22
-47%
$843
$450 per night
House ∙ 14 guests ∙ 3 bedrooms
House in Winter Park with Grill + Gorgeous Views
5.0
Outstanding (104 ratings)
Winter Park, Grand County, Colorado, United States
Internet
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House  Winter Park
Oct 7 - Oct 14
-25%
$228
$171 per night
House ∙ 7 guests ∙ 3 bedrooms
Nice House in Fraser with Wood-Burning Fireplace + Great View
4.9
Outstanding (72 ratings)
Winter Park, Grand County, Colorado, United States
Internet
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Winter Park by booking a vacation home with a fireplace.

Condo  Winter Park
Dec 2 - Dec 9
-77%
$541
$125 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Nice Condo in Fraser with Electric Fireplace + Mountain Views
4.4
Very good (6 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
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Condo  Winter Park
Oct 6 - Oct 13
-71%
$195
$57 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Winter Park with Wood-Burning Fireplace
3.7
Good (18 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
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House  Winter Park
Nov 4 - Nov 11
-85%
$754
$115 per night
House ∙ 9 guests ∙ 4 bedrooms
House in Granby with Grill + Incredible Views
5.0
Outstanding
Winter Park, Grand County, Colorado, United States
Fireplace
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Popular Rental Amenities in Winter Park

  • Pet-friendly (359)
  • Pool (1,619)
  • Hot tub (1,215)
  • WiFi (3,740)
  • Fireplace (3,462)
  • Kitchen (3,646)
  • Washing machine (2,301)
  • TV (3,513)
  • Balcony/patio (361)
  • Parking (917)
  • No smoking (2,738)
  • Grill (1,988)

Our search page's filters will help you find the ideal rental in Winter Park. HomeToGo's data reveals that "Pets allowed" and "Pool" are the most commonly offered amenities in Winter Park. Plan your vacation in advance if you want to spend your vacation in privacy or you need a crib for your baby. There are just 35 listed rentals with "Detached" and 724 properties with "Crib."

Price and Availability Index in Winter Park

Click on any bar to see price and availability information

Vacation Rental Price Information in Winter Park

The graph shows the average rental prices for the next twelve months in Winter Park. It is during a week of December (12/23 - 12/30) that you will find the highest prices for the next 12 months. Prices decrease in a week of September (9/7 - 9/14), where average prices are $265.

Rental availability information in Winter Park

Our availability graph helps you identify the busiest months in Winter Park. The most challenging week to find a rental in the next twelve months is in September (9/7 - 9/14). Conversely, you will find the highest percentage of available offers in Winter Park in October (10/14 - 10/21).

The Weather in Winter Park

max.
Min.
16°
18 days 18
max.
Min.
19°
20 days 20
max.
Min.
27°
14°
11 days 11
max.
Min.
28°
16°
20 days 20
max.
Min.
34°
23°
22 days 22
max.
Min.
52°
36°
13 days 13
max.
Min.
54°
39°
20 days 20
max.
Min.
50°
37°
20 days 20
max.
Min.
46°
34°
14 days 14
max.
Min.
36°
23°
13 days 13
max.
Min.
23°
12°
15 days 15
max.
Min.
16°
19 days 19
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Winter Park. During July, maximum temperatures go up to more than 54° On the other hand, you could have temperatures dropping under 5° in December. The rainiest month is May while the driest month is March.

7-Day Weather Forecast in Winter Park

Wed, 27 Sep
66°
44°

0%

8 h

8 mi/h

Thu, 28 Sep
69°
44°

10%

11 h

4 mi/h

Fri, 29 Sep
69°
48°

0%

8 h

5 mi/h

Sat, 30 Sep
62°
37°

0%

11 h

13 mi/h

Sun, 1 Oct
59°
30°

0%

10 h

7 mi/h

Mon, 2 Oct
66°
39°

0%

11 h

7 mi/h

Tue, 3 Oct
68°
42°

10%

9 h

8 mi/h

Accommodations for your vacation in Winter Park

Users who are searching for house rental in Winter Park will have a lot of options to choose from, as they are the most typical accomodations being offered in this destination. In addition, the average size of house rental in Winter Park is 206 m² and they cost, on average, $637 a night. Furthermore, if you are going in a group of 10, house rental are the perfect accommodation type in Winter Park, as they usually welcome this exact group size. Users looking for something other than house rental can also compare many apartment rental, which are the other most popular accommodation type in Winter Park. The average size of apartment rental in Winter Park is 123 m², and the average price is $437 per night.
Where to find the best food in Winter Park?

A variety of mountainside cuisine

Roll into The Ditch On 40 for burgers and Southwestern fare. The menu's signature item, New Mexican Juantons, are egg rolls with a twist, containing green chilis, garlic, ground chuck, and sharp cheddar.

Get your crêpe fix at Goodys Mountain Cafe & Creperie, where their doughy creations along with steaming coffee will keep you racing on the slopes all morning long. For steaks and classic bistro fare in an upscale setting, head to Deno's, which offers everything from pizza and burgers to seafood.

What are the best activities for families in Winter Park?

Young mountaineers

Beyond ski school, children can enjoy tubing, ice skating, and snowshoeing. In summer, Winter Park, despite a name reminiscent of endless snow, is just as exciting. The resort's alpine slide is the longest of its kind in mountainous Colorado. Kids can fly down the hill in joy on the safe yet thrilling track.

Treat kids to a day out fishing at one of the area's child-friendly ponds. The stocked North Pond at Lion's Fishing Ponds is suitable for ages 14 and younger, while the stocked pond at Kaibab Park is for those 15 and under. Casting a line should get some bites!

Where are the unique attractions in Winter Park?

Adrenaline rushes

Winter Park Ski Resort is one of the top, best-known ski resorts in Colorado, not to mention the longest-running, at 75 years old. Explore seven territories of highly varied terrain, from challenging moguls in Mary Jane Territory to backcountry-like Vasquez Ridge.

Colorado has a collection of 53 extra-tall mountains over 14,000 feet, referred to locally as "14-ers." Winter Park is home to a few of these mammoths, with the closest and least difficult pair being Mount Bierstadt and Mount Evans.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 3,379 homes
💳 Possible discounts up to 56%
🌙 Nightly prices starting at $47
⭐ Popular amenities Pets allowed, Pool and Hot tub
🐾 Pet friendly homes 279 homes
🏊 Vacation rentals with pools 1,428 homes

Frequently Asked Questions

What is the typical nightly price for a vacation home in Winter Park?

The nightly price of accommodations in Winter Park starts at $47. If you’re interested in a house rental, the average price is $637 per night. A apartment rental Winter Park will cost $437 per night on average.

How many vacation homes are available for booking in Winter Park?

There are currently 3,379 rentals to choose from for your upcoming vacation.

What are the most popular amenities for vacation homes in Winter Park?

Three most popular amenities for home rentals in Winter Park include accommodations with: Pool, Pets allowed, and Hot tub.

How many vacation rentals with pools are in Winter Park?

There are 1,428 vacation homes from 8 providers in Winter Park.

Are pets allowed in vacation rentals in Winter Park?

Finding a vacation home in Winter Park that allows pets is possible, with 279 pet-friendly available.

When is it better to travel to Winter Park?

If you are looking for a vacation rental in Winter Park, consider that rainy season is usually in May or February, with March often being the driest.

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