Vacation rentals in Winter Park

Vacation rentals in Winter Park

Start comparing over 456 rentals in Winter Park and book at the best price!

Find offers

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

Vacation Rentals in Winter Park

Vacation rental for 2 people in Winter Park
Vacation rental for 2 people
1 bedroom
4.5
(11 reviews)
from $146 / night
Vacation rental for 4 people, with balcony and pool as well as sauna in Winter Park
Vacation rental for 4 people, with balcony and pool as well as sauna
1 bedroom
4.6
(21 reviews)
from $77 / night
Vacation rental for 5 people, with balcony in Winter Park
Vacation rental for 5 people, with balcony
2 bedrooms
5.0
(9 reviews)
from $175 / night
Vacation rental for 4 people, with sauna and pool as well as balcony in Winter Park
Vacation rental for 4 people, with sauna and pool as well as balcony
4.5
(20 reviews)
from $91 / night

Popular Vacation Rentals in Winter Park

Vacation rental for 6 people, with hot tub, kid friendly in Winter Park
Vacation rental for 6 people, with hot tub, kid friendly
1 bedroom
4.0
(200 reviews)
from $126 / night
Vacation rental for 4 people, with pool in Winter Park
Vacation rental for 4 people, with pool
4.5
(9 reviews)
from $75 / night
Vacation rental for 2 people, with balcony and hot tub in Winter Park
Vacation rental for 2 people, with balcony and hot tub
4.2
(5 reviews)
from $154 / night
Vacation rental for 2 people, with balcony and hot tub in Winter Park
Vacation rental for 2 people, with balcony and hot tub
1 bedroom
from $223 / night

Vacation rentals with free cancellation

Hotel for 2 people, with sauna and pool in Winter Park
Hotel for 2 people, with sauna and pool
1 bedroom
3.4
(403 reviews)
from $144 / nightFREE cancellation
Hotel for 3 people, with hot tub in Winter Park
Hotel for 3 people, with hot tub
1 bedroom
3.6
(24 reviews)
from $112 / nightFREE cancellation
Hotel for 4 people, with pets in Winter Park
Hotel for 4 people, with pets
1 bedroom
4.2
(361 reviews)
from $162 / nightFREE cancellation
Hotel for 4 people, with hot tub, with pets in Winter Park
Hotel for 4 people, with hot tub, with pets
1 bedroom
4.3
(592 reviews)
from $137 / nightFREE cancellation

Pet-friendly Vacation Rentals

Vacation rental for 4 people, with balcony and hot tub, with pets in Winter Park
Vacation rental for 4 people, with balcony and hot tub, with pets
2 bedrooms
4.8
(4 reviews)
from $227 / night
Vacation rental for 8 people, with pets in Winter Park
Vacation rental for 8 people, with pets
2 bedrooms
4.5
(21 reviews)
from $140 / night
Vacation rental for 6 people, with pets in Winter Park
Vacation rental for 6 people, with pets
2 bedrooms
4.9
(6 reviews)
from $177 / night
Vacation rental for 9 people, with balcony in Winter Park
Vacation rental for 9 people, with balcony
4 bedrooms
4.9
(19 reviews)
from $384 / night

Vacation Rentals with Pool

Vacation rental for 4 people, with pool and balcony in Winter Park
Vacation rental for 4 people, with pool and balcony
4.6
(7 reviews)
from $142 / night
Vacation rental for 4 people, with hot tub and pool in Winter Park
Vacation rental for 4 people, with hot tub and pool
1 bedroom
3.7
(6 reviews)
from $152 / night
Vacation rental for 4 people, with pool and balcony in Winter Park
Vacation rental for 4 people, with pool and balcony
5.0
(9 reviews)
from $116 / night
Vacation rental for 4 people, with pool and sauna as well as yard in Winter Park
Vacation rental for 4 people, with pool and sauna as well as yard
1 bedroom
4.9
(20 reviews)
from $165 / night

Vacation Rentals with Internet

Vacation rental for 4 people, with balcony and hot tub in Winter Park
Vacation rental for 4 people, with balcony and hot tub
1 bedroom
from $218 / night
Vacation rental for 4 people, with balcony in Winter Park
Vacation rental for 4 people, with balcony
1 bedroom
from $272 / night
Vacation rental for 4 people in Winter Park
Vacation rental for 4 people
from $202 / night
Vacation rental for 4 people, with balcony and hot tub in Winter Park
Vacation rental for 4 people, with balcony and hot tub
1 bedroom
4.6
(20 reviews)
from $184 / night

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 12
Internet 342
Pets allowed 35
Balcony/Terrace 260
TV 328
Air conditioning 14

Other property types in Winter Park that might be interesting:

Prices and availability

Vacation rental prices Winter Park

$419for 20 Aug - 27 Aug
$469 annual average
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Average price per week

Vacation rentals availability Winter Park

1%for 20 Aug - 27 Aug
53% annual average
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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

What is the average price for vacation rentals in Winter Park?

Our data shows that Winter Park had an average price of $460 per night, a relatively high one for a city in the USA.

What time of year offers, on average, the best vacation rental prices in Winter Park?

If you want to save the maximum during your vacation to Winter Park, go there in May ($372 per night on average), October ($388), or April ($400), to find the lowest prices for the whole year.

When are vacation rentals more expensive in Winter Park?

When it comes to looking for a vacation rental in Winter Park, the months when it is most expensive are, in order of highest to lowest, January, December and March, with average prices per night of $593, $555, and $550, respectively.

Is it necessary to plan a trip to Winter Park well in advance?

It's worthwhile to be proactive in Winter Park as only 21% of the properties are available throughout the year, following the data observed in the previous year.

What are the best months for a last-minute getaway?

The most available months are, on average, October (with an availability of 65%), September (53%), and November (49%), according to the trends observed in the prior year.

How many vacation rentals are there in Winter Park?

We have collected the offers from 3 different partners in Winter Park, so we can provide you with around 1,100 properties. You're going to have a hard time picking your favorite!

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

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  2. USA
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