Vacation rentals in Winter Park

Vacation rentals in Winter Park

Start comparing over 307 rentals in Winter Park and book at the best price!

Search millions of vacation rentals
+
Compare over 1500 websites
=
Find your perfect vacation rental at the best price

Find offers

Free cancellation
Vacation house
Vacation apartment
Pool
Internet
Pets allowed
4.0
& higher
4.5
& higher

Popular Vacation Rentals in Winter Park

from
$157
per night
Log cabin for 8 people, with pets
8 pers.2 bedrooms1,421ft²
4.2
(20 reviews)
from
$155
per night
Vacation rental for 4 people, with pool and jacuzzi
4 pers.1 bedroom
FREE cancellation
3.9
(9 reviews)
from
$150
per night
Vacation rental for 8 people, with balcony and jacuzzi
8 pers.3 bedrooms
FREE cancellation
5.0
(3 reviews)
show all

Vacation rentals with free cancellation

from
$141
per night
Vacation rental for 6 people
6 pers.2 bedrooms
FREE cancellation
from
$196
per night
Vacation rental for 4 people, with jacuzzi
4 pers.1 bedroom560ft²
FREE cancellation
4.8
(20 reviews)
from
$187
per night
Vacation rental for 6 people, with jacuzzi
6 pers.2 bedrooms
FREE cancellation
0.1
show all

Vacation Rentals in Winter Park

from
$421
per night
Vacation rental for 9 people, with balcony and jacuzzi
9 pers.3 bedrooms1,496ft²
FREE cancellation
5.0
(6 reviews)
from
$497
per night
Vacation rental for 14 people, with jacuzzi
14 pers.5 bedrooms2,293ft²
FREE cancellation
5.0
(3 reviews)
from
$81
per night
Vacation rental for 5 people, with jacuzzi
5 pers.1 bedroom549ft²
FREE cancellation
4.9
(20 reviews)
from
$169
per night
Vacation rental for 6 people
6 pers.3 bedrooms1,496ft²
5.0
from
$162
per night
Vacation rental for 4 people, with pool and jacuzzi
4 pers.1 bedroom
FREE cancellation
3.7
(12 reviews)
from
$495
per night
Vacation rental for 12 people, with pool and balcony as well as jacuzzi
12 pers.4 bedrooms
FREE cancellation
4.9
(20 reviews)
show all

Pet-friendly Vacation Rentals

from
$189
per night
Vacation rental for 8 people, with balcony and jacuzzi
8 pers.3 bedrooms1,356ft²
FREE cancellation
3.6
(10 reviews)
from
$158
per night
Vacation rental for 7 people, with jacuzzi and pool, with pets
7 pers.2 bedrooms1,259ft²
FREE cancellation
4.2
(4 reviews)
from
$187
per night
Vacation rental for 8 people, with balcony and jacuzzi, with pets
8 pers.3 bedrooms2,099ft²
show all

Vacation Rentals with Pool

from
$121
per night
Vacation rental for 4 people, with pool and jacuzzi as well as balcony, child-friendly
4 pers.1 bedroom
FREE cancellation
4.0
(111 reviews)
from
$127
per night
Vacation rental for 6 people, with balcony and pool as well as sauna and jacuzzi
6 pers.2 bedrooms700ft²
FREE cancellation
4.0
(23 reviews)
from
$139
per night
Vacation rental for 7 people, with jacuzzi and pool
7 pers.2 bedrooms1,195ft²
FREE cancellation
4.8
(20 reviews)
show all

Vacation Rentals with Internet

from
$112
per night
Vacation rental for 4 people, with jacuzzi and balcony
4 pers.1 bedroom560ft²
4.7
(12 reviews)
from
$178
per night
Vacation rental for 4 people
4 pers.1 bedroom398ft²
FREE cancellation
from
$168
per night
Vacation rental for 10 people, with balcony and jacuzzi
10 pers.3 bedrooms1,485ft²
4.4
(2 reviews)
show all

Find Vacation Rentals in Winter Park

Map

Highlights Winter Park

  • Mountain rentals
  • Outdoor activities
  • Nature lover destination
  • Spring break destination
  • Family destination
  • Hiking trails
  • Scenic landscape

Most popular in Winter Park

Pool 148
Internet 338
Pets allowed 35
Balcony/Terrace 242
TV 332
Air conditioning 12

Other property types in Winter Park that might be interesting:

Prices and availability

Prices

November
December
January
February
March
$726
Average price per week

Availabilities

November
December
January
February
March
68 %
Percentage of available rentals

Vacation rentals in Winter Park

Splendid rental locations in Colorado

Located just a short drive from the notorious Rocky Mountain National Park, Winter Park is the ideal getaway for any traveler looking to enjoy a vacation in the middle of nature. The city is situated in Grand County, United States and its permanent population is just 999 inhabitants, however, it has over 2,500 housing units within the town limits. In Winter Park you will be able to find over 359 miles of nature trails, over 150 alpine lakes, almost 100 species of mammals and countless camping spots. You will be able to find many opportunities in Winter Park, such as cross-country skiing, mountain biking, concerts, hiking and fishing. The climate of the area is quite ideal as the mountain is snow-covered for half the year and provides a warm sunny climate in the summer.

Discover the vacation rentals

Surrounded by such a scenic landscape, you will be delighted by the beautiful vacation rentals you will encounter in Winter Park. Spend your morning making breakfast while admiring the white snowy mountains outside your window, cozy up by the fireplace on your private patio while having a nice cup of hot chocolate, cook some barbecue on your terrace with some friends during the warmer days. These are just a few of the many memories you could be making in Winter Park.

Vacations in Winter Park

How to get there and what to do

Explore the mountains of Colorado

Winter Park might be nestled in the middle of the mountains, however, making your journey to the city will be a breeze. There are plenty of modes of transportation you can choose from while planning your journey to Winter Park. If you choose to make the journey by car, you will find that Interstate 70 west and the US Highway 40 are the main roads that will take you to Winter Park. On the other hand, if you want to fly to your destination, the Denver International Airport is the closest airport to the city and it caters flights to major cities all around the United States. From the airport, you will be able to take a shuttle service or a charter bus directly to Winter Park. Lastly, making the journey by train is easy with the Winter Park Express which is run by Amtrak and will take you directly into the center of the city.

Where to eat in Winter Park

After a full day of adventuring through the outdoors you must be curious to find a good to fill your stomach. Winter Park has plenty of choices when it comes to eateries, whether you want to eat barbecue or something exotic. Warm-up after a cold day in the mountains at the Idlewild Distillery. This local distillery makes its whiskey, as well as offering gin, grappa and coffee liqueur. Moreover, their menu is filled with delicious items such as the BBW Bacon Cheddar Burger and their Charcuterie board. On the other hand, the Carver’s Bakery Café is the ideal spot for a delicious breakfast. This cute little café will provide you with traditional American staples such as Belgian waffles, French toast, eggs benedict and huevos rancheros.

Travelers and activities

Winter Park for outdoor activities

Known for its long biking routes, Winter Park is the perfect destination for travelers that wish to go on a bike ride around its flora and fauna. From the numerous trails around the city, Idlewild Trail System is one of the longest. Here you will be able to find a combination of a challenging course and long distances, however at an intermediate level. The Rainmaker, which is located in the Trestle Bike Park, is a singletrack downhill trail that spans 3.3 miles. This Black Diamond trail is for the more expert riders.

Winter Park for families

There are plenty of fun activities to enjoy while visiting Winter Park with your family. The Coca-Cola Tubing Hill is the perfect location to bring kids on a snowy day. Here you will be able to rent sledges and take advantage of a magic carpet that will bring you to the top of the hill. Another fun activity for the entire family is taking part in the Grand Adventure Balloon Tour. Take a chance to admire the city from up above on a hot air balloon. The tour will last a couple of hours and you will be able to see all the surrounding mountains of Winter Park.

„Did you know that Winter Park is the mountain bike capital of the United States with over 600 miles of trails?“

Top 5 travel tips for Winter Park

1. Moffat Tunnel

Discover local history while visiting this tunnel which cuts through the Continental Divide. This tunnel was created in 1928 and named after a railroad pioneer named David Moffat.

2. James Peak

Immerse yourself in the wilderness by visiting James Peak. Here you will be able to take in a scenic landscape while hiking through its trail that reaches a summit lake. The lake is also known for trout fishing.

3. Eldora Mountain

One of the most stunning mountains in the area, Eldora Mountain is the place to be for anything that involves snow. Here you will be able to rent out ski or snowboards, as well as go cross-country skiing.

4. Berthoud Pass

Another ideal spot for scenic landscapes is the Berthoud Pass. If you are looking for an easier hiking trail with satisfying views, do not miss out on this location.

5. Arapaho and Roosevelt National Forests

Explore the wilderness of Winter Park while strolling through this national forest. The forest was established in 1908 by Theodore Roosevelt and it was named for the Arapaho tribe of Native Americans who inhabited the area.

Vacation rentals in Winter Park

Splendid rental locations in Colorado

Located just a short drive from the notorious Rocky Mountain National Park, Winter Park is the ideal getaway for any traveler looking to enjoy a vacation in the middle of nature. The city is situated in Grand County, United States and its permanent population is just 999 inhabitants, however, it has over 2,500 housing units within the town limits. In Winter Park you will be able to find over 359 miles of nature trails, over 150 alpine lakes, almost 100 species of mammals and countless camping spots. You will be able to find many opportunities in Winter Park, such as cross-country skiing, mountain biking, concerts, hiking and fishing. The climate of the area is quite ideal as the mountain is snow-covered for half the year and provides a warm sunny climate in the summer.

Discover the vacation rentals

Surrounded by such a scenic landscape, you will be delighted by the beautiful vacation rentals you will encounter in Winter Park. Spend your morning making breakfast while admiring the white snowy mountains outside your window, cozy up by the fireplace on your private patio while having a nice cup of hot chocolate, cook some barbecue on your terrace with some friends during the warmer days. These are just a few of the many memories you could be making in Winter Park.

Vacations in Winter Park

How to get there and what to do

Explore the mountains of Colorado

Winter Park might be nestled in the middle of the mountains, however, making your journey to the city will be a breeze. There are plenty of modes of transportation you can choose from while planning your journey to Winter Park. If you choose to make the journey by car, you will find that Interstate 70 west and the US Highway 40 are the main roads that will take you to Winter Park. On the other hand, if you want to fly to your destination, the Denver International Airport is the closest airport to the city and it caters flights to major cities all around the United States. From the airport, you will be able to take a shuttle service or a charter bus directly to Winter Park. Lastly, making the journey by train is easy with the Winter Park Express which is run by Amtrak and will take you directly into the center of the city.

Where to eat in Winter Park

After a full day of adventuring through the outdoors you must be curious to find a good to fill your stomach. Winter Park has plenty of choices when it comes to eateries, whether you want to eat barbecue or something exotic. Warm-up after a cold day in the mountains at the Idlewild Distillery. This local distillery makes its whiskey, as well as offering gin, grappa and coffee liqueur. Moreover, their menu is filled with delicious items such as the BBW Bacon Cheddar Burger and their Charcuterie board. On the other hand, the Carver’s Bakery Café is the ideal spot for a delicious breakfast. This cute little café will provide you with traditional American staples such as Belgian waffles, French toast, eggs Benedict and huevos rancheros.

Travelers and activities

Winter Park for outdoor activities

Known for its long biking routes, Winter Park is the perfect destination for travelers that wish to go on a bike ride around its flora and fauna. From the numerous trails around the city, Idlewild Trail System is one of the longest. Here you will be able to find a combination of a challenging course and long distances, however at an intermediate level. The Rainmaker, which is located in the Trestle Bike Park, is a single track downhill trail that spans 3.3 miles. This Black Diamond trail is for the more expert riders.

Winter Park for families

There are plenty of fun activities to enjoy while visiting Winter Park with your family. The Coca-Cola Tubing Hill is the perfect location to bring kids on a snowy day. Here you will be able to rent sledges and take advantage of a magic carpet that will bring you to the top of the hill. Another fun activity for the entire family is taking part in the Grand Adventure Balloon Tour. Take a chance to admire the city from up above on a hot air balloon. The tour will last a couple of hours and you will be able to see all the surrounding mountains of Winter Park.

„Did you know that Winter Park is the mountain bike capital of the United States with over 600 miles of trails?“

Top 5 travel tips for Winter Park

1. Moffat Tunnel

Discover local history while visiting this tunnel which cuts through the Continental Divide. This tunnel was created in 1928 and named after a railroad pioneer named David Moffat.

2. James Peak

Immerse yourself in the wilderness by visiting James Peak. Here you will be able to take in a scenic landscape while hiking through its trail that reaches a summit lake. The lake is also known for trout fishing.

3. Eldora Mountain

One of the most stunning mountains in the area, Eldora Mountain is the place to be for anything that involves snow. Here you will be able to rent out ski or snowboards, as well as go cross-country skiing.

4. Berthoud Pass

Another ideal spot for scenic landscapes is the Berthoud Pass. If you are looking for an easier hiking trail with satisfying views, do not miss out on this location.

5. Arapaho and Roosevelt National Forests

Explore the wilderness of Winter Park while strolling through this national forest. The forest was established in 1908 by Theodore Roosevelt and it was named for the Arapaho tribe of Native Americans who inhabited the area.

Vacation rentals in Winter Park

Splendid rental locations in Colorado

Located just a short drive from the notorious Rocky Mountain National Park, Winter Park is the ideal getaway for any traveler looking to enjoy a vacation in the middle of nature. The city is situated in Grand County, United States and its permanent population is just 999 inhabitants, however, it has over 2,500 housing units within the town limits. In Winter Park you will be able to find over 359 miles of nature trails, over 150 alpine lakes, almost 100 species of mammals and countless camping spots. You will be able to find many opportunities in Winter Park, such as cross-country skiing, mountain biking, concerts, hiking and fishing. The climate of the area is quite ideal as the mountain is snow-covered for half the year and provides a warm sunny climate in the summer.

Discover the vacation rentals

Surrounded by such a scenic landscape, you will be delighted by the beautiful vacation rentals you will encounter in Winter Park. Spend your morning making breakfast while admiring the white snowy mountains outside your window, cozy up by the fireplace on your private patio while having a nice cup of hot chocolate, cook some barbecue on your terrace with some friends during the warmer days. These are just a few of the many memories you could be making in Winter Park.

Vacations in Winter Park

How to get there and what to do

Explore the mountains of Colorado

Winter Park might be nestled in the middle of the mountains, however, making your journey to the city will be a breeze. There are plenty of modes of transportation you can choose from while planning your journey to Winter Park. If you choose to make the journey by car, you will find that Interstate 70 west and the US Highway 40 are the main roads that will take you to Winter Park. On the other hand, if you want to fly to your destination, the Denver International Airport is the closest airport to the city and it caters flights to major cities all around the United States. From the airport, you will be able to take a shuttle service or a charter bus directly to Winter Park. Lastly, making the journey by train is easy with the Winter Park Express which is run by Amtrak and will take you directly into the center of the city.

Where to eat in Winter Park

After a full day of adventuring through the outdoors you must be curious to find a good to fill your stomach. Winter Park has plenty of choices when it comes to eateries, whether you want to eat barbecue or something exotic. Warm-up after a cold day in the mountains at the Idlewild Distillery. This local distillery makes its whiskey, as well as offering gin, grappa and coffee liqueur. Moreover, their menu is filled with delicious items such as the BBW Bacon Cheddar Burger and their Charcuterie board. On the other hand, the Carver’s Bakery Café is the ideal spot for a delicious breakfast. This cute little café will provide you with traditional American staples such as Belgian waffles, French toast, eggs benedict and huevos rancheros.

Travelers and activities

Winter Park for outdoor activities

Known for its long biking routes, Winter Park is the perfect destination for travelers that wish to go on a bike ride around its flora and fauna. From the numerous trails around the city, Idlewild Trail System is one of the longest. Here you will be able to find a combination of a challenging course and long distances, however at an intermediate level. The Rainmaker, which is located in the Trestle Bike Park, is a single track downhill trail that spans 3.3 miles. This Black Diamond trail is for the more expert riders.

Winter Park for families

There are plenty of fun activities to enjoy while visiting Winter Park with your family. The Coca-Cola Tubing Hill is the perfect location to bring kids on a snowy day. Here you will be able to rent sledges and take advantage of a magic carpet that will bring you to the top of the hill. Another fun activity for the entire family is taking part in the Grand Adventure Balloon Tour. Take a chance to admire the city from up above on a hot air balloon. The tour will last a couple of hours and you will be able to see all the surrounding mountains of Winter Park.

„Did you know that Winter Park is the mountain bike capital of the United States with over 600 miles of trails?“

Top 5 travel tips for Winter Park

1. Moffat Tunnel

Discover local history while visiting this tunnel which cuts through the Continental Divide. This tunnel was created in 1928 and named after a railroad pioneer named David Moffat.

2. James Peak

Immerse yourself in the wilderness by visiting James Peak. Here you will be able to take in a scenic landscape while hiking through its trail that reaches a summit lake. The lake is also known for trout fishing.

3. Eldora Mountain

One of the most stunning mountains in the area, Eldora Mountain is the place to be for anything that involves snow. Here you will be able to rent out ski or snowboards, as well as go cross-country skiing.

4. Berthoud Pass

Another ideal spot for scenic landscapes is the Berthoud Pass. If you are looking for an easier hiking trail with satisfying views, do not miss out on this location.

5. Arapaho and Roosevelt National Forests

Explore the wilderness of Winter Park while strolling through this national forest. The forest was established in 1908 by Theodore Roosevelt and it was named for the Arapaho tribe of Native Americans who inhabited the area.

FAQs: Vacation Rentals in Winter Park

How much did it cost for a vacation rental in Winter Park in 2020, the first year impacted by the corona crisis?

At an average cost of $386.30 per night, Winter Park lies at the upper end of the price range for vacation rentals in the USA.

During which months can you find the best price for vacation rentals in Winter Park?

Travelers who want to save as much as possible visit Winter Park in June, May, and October, the cheapest months of the year, with average prices of $329.21, $333.28, and $341.26 per night, respectively, based on data collected in 2020.

When does the price of vacation rentals in Winter Park go up the most?

Analyzing the data from 2020, we found that costs per night for accommodation here are usually higher, on average, during the months of March ($487.52), January ($470.5), and February ($455.62).

Is Winter Park a good location for a last-minute getaway?

It is better to plan ahead in Winter Park as only 29% of the accommodations remain free throughout the year, according to our 2020 data.

What are the best months for a spontaneous getaway?

In 2020, the months with the largest number of properties available of the year in Winter Park were June, October and November, with average availabilities of 48.75%, 41.8%, and 41.5%, respectively.

Which months is it more difficult to find available vacation rentals?

The months with the lowest properties available in Winter Park are, in order, February, January, and March with respective average availability figures of 4%, 8.5%, and 16.25%, based on data collected in 2020.

Are there many rentals in Winter Park?

We have 880 rentals for you in Winter Park, provided by our 4 local and international partners.

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

Booking.com Vacation Rentals in Winter ParkBooking.com Vacation Rentals in Winter ParkHomeAway Vacation Rentals in Winter ParkHomeAway Vacation Rentals in Winter ParkFeWo-direkt Vacation Rentals in Winter ParkFeWo-direkt Vacation Rentals in Winter ParkVrbo Vacation Rentals in Winter ParkVrbo Vacation Rentals in Winter ParkHRS Vacation Rentals in Winter ParkHRS Vacation Rentals in Winter ParkAbritel Vacation Rentals in Winter ParkAbritel Vacation Rentals in Winter ParkAirbnb Vacation Rentals in Winter ParkAirbnb Vacation Rentals in Winter Park
  1. Vacation Rentals
  2. USA
  3. Colorado
  4. Rocky Mountain National Park
  5. Winter Park