Photo by Winter Park Resort

Winter Park holiday rentals

We found 2,044 holiday rentals — enter your dates for availability
Select from 336 houses, 497 flats and other holiday rentals to find the perfect place for your stay in Winter Park. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Winter Park

Showing deals for:25 Dec - 1 Jan

Main Living Open to Dining Room and Kitchen
Wrap around porch
View from Hot Tub
Hot Tub
Exceptional
(136 reviews)

Elk Court Luxury Mountain Retreat, Sleeps up to 16 people

Winter Park

9% off
S$14,197
for 7 nights, 1 home
S$2,028 per night
includes taxes & fees
Elk Court Luxury Mountain Retreat, Sleeps up to 16 people
Firepit on the lower deck looking up at the back of Oso's Overlook.
The Wild West suite - private bath, sitting area, fireplace, and office area
Looking up at the back of Oso's from private road below, in the fall
Wild West Suite's private office area, fireplace and sitting room.
Exceptional
(52 reviews)

7 Acre Mountain Retreat: 7 bdrms 7.5 ba gourmet kitchen; ski raft hike fish bike

Winter Park

9% off
S$15,928
for 7 nights, 1 home
S$2,275 per night
includes taxes & fees
7 Acre Mountain Retreat: 7 bdrms 7.5 ba gourmet kitchen; ski raft hike fish bike
Room
Living area
Interior
Private kitchen
Exceptional
(83 reviews)

Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!

Winter Park

8% off
S$8,800
for 7 nights, 1 home
S$1,257 per night
includes taxes & fees
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Private kitchen
Private kitchen
Interior
Property grounds
Exceptional
(83 reviews)

Adorable Cottage in National Forest -- hiking & climbing steps from your door!

Dumont

8% off
S$2,114
for 7 nights, 1 home
S$302 per night
includes taxes & fees
Adorable Cottage in National Forest -- hiking & climbing steps from your door!
Brand New private 7-8 person hot tub on lower level patio.
Main level living room with queen sofa sleeper.
Exterior
Main level living room.
Exceptional
(18 reviews)

The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!

Fraser

9% off
S$8,706
for 7 nights, 1 home
S$1,244 per night
includes taxes & fees
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
Unit perched on the top floor with spectacular views and privacy!
Enjoy the sunset from the private back deck.
Gather around beautiful solid wood table that comfortably seats eight
Huge great room to socialize with family and friends
Exceptional
(57 reviews)

Gorgeous luxury top floor condo! Stunning Mountain Views! Private decks! Garage

Fraser

12% off
S$6,460
for 7 nights, 1 apartment
S$923 per night
includes taxes & fees
Gorgeous luxury top floor condo! Stunning Mountain Views! Private decks! Garage
Pool and hot tub at the clubhouse
Property grounds
Clubhouse
Mary Jane Trail top
Exceptional
(82 reviews)

Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!

Winter Park

8% off
S$7,862
for 7 nights, 1 apartment
S$1,123 per night
includes taxes & fees
Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
Open Floor Plan Living, Dining, Kitchen
Kitchen into Living Spaces
Dining & Kitchen
Deck
Exceptional
(28 reviews)

Penthouse Cozy Condo in the heart of Downtown Winter Park

Winter Park

8% off
S$8,426
for 7 nights, 1 apartment
S$1,204 per night
includes taxes & fees
Penthouse Cozy Condo in the heart of Downtown Winter Park
Living area
Pool
Exterior
Dining
Wonderful
(19 reviews)

Superb Mountain Getaway- 2BR+2BA

Fraser

8% off
S$2,986
for 7 nights, 1 apartment
S$427 per night
includes taxes & fees
Superb Mountain Getaway- 2BR+2BA
Interior
Room
Private kitchen
Interior
Exceptional
(15 reviews)

Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4

Winter Park

8% off
S$4,318
for 7 nights, 1 apartment
S$617 per night
includes taxes & fees
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Interior
Living area
Master bedroom deck with amazing views!
a wall of southwest windows in the living room facing the back yard
Exceptional
(80 reviews)

Private Mountain Home. Hot Tub. Dog-Friendly. 10 Min to Winter Park Resort

Fraser

8% off
S$8,257
for 7 nights, 1 home
S$1,180 per night
includes taxes & fees
Private Mountain Home. Hot Tub. Dog-Friendly. 10 Min to Winter Park Resort
Rec Center Workout room
Rec Center sitting area w/ TV
Rec Center deck w/ outdoor hottub
Rec Center Pool
Exceptional
(31 reviews)

Cozy 1 Bedroom Hi Country Haus - on river !

Winter Park

8% off
S$2,312
for 7 nights, 1 apartment
S$330 per night
includes taxes & fees
Cozy 1 Bedroom Hi Country Haus - on river !
Private kitchen
Property grounds
Terrace/patio
Interior
Exceptional
(148 reviews)

WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH

Winter Park

8% off
S$7,771
for 7 nights, 1 apartment
S$1,110 per night
includes taxes & fees
WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH
Private kitchen
Interior
Room
Living area
Exceptional
(16 reviews)

New Luxury 3-Bedroom Condo 1/2 Block to Main St

Winter Park

6% off
S$9,247
for 7 nights, 1 apartment
S$1,321 per night
includes taxes & fees
New Luxury 3-Bedroom Condo 1/2 Block to Main St

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The cosy city of Winter Park awaits you

Enjoy the live music and other features of Winter Park. Renowned for its skiing, mountain views and snowboarding, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Winter Park

Do you want to find attractions to see during your stay? Travellers enjoy Winter Park for its skiing, snowboarding and hiking. Venture out of your cosy holiday rental and experience everything that makes Winter Park a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Winter Park Ski Resort (3.7 mi / 5.9 km)
  • Trestle Bike Park (2.5 mi / 4.1 km)
  • Pole Creek Golf Club (7.7 mi / 12.3 km)
  • Ski Granby Ranch (10.3 mi / 16.6 km)
  • Eldora Mountain Resort (10.7 mi / 17.3 km)
  • Grand Elk Golf Club (13.1 mi / 21.1 km)

Exploring the mountains and other natural features in Winter Park

Whether you're an adventurous traveller or just want to appreciate the scenery, Winter Park is a great place to spend some time outside. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Rocky Mountain National Park (29.7 mi / 47.9 km)
  • The Fraser River Trail (2.6 mi / 4.1 km)
  • Saint Mary's Glacier (9.2 mi / 14.8 km)
  • Georgetown Lake (14.1 mi / 22.7 km)
  • Torreys Peak (16 mi / 25.8 km)
  • Lake Granby (16.4 mi / 26.3 km)

Seasonal weather averages in Winter Park

Winter Park is well known for its skiing. If you're interested in winter sports, you might consider visiting in January, February, March or April, when snowfall averages 67 cm and temperatures average -8°C.

Travelling to and around Winter Park

The nearest airport is in Broomfield, CO (BJC-Rocky Mountain Metropolitan), located 35.7 mi (57.4 km) from the city centre.

If you'd prefer to travel by train, the main station is Winter Park Ski Resort Amtrak Station.

Frequently asked questions

What is the best area to stay in Winter Park when booking a holiday rental?
Old Town Winter Park is one of the more sought-after locations for a holiday property in Winter Park. Spend your stay here to savour the comfort and privacy that comes with having the entire place to yourself.
What is the most popular type of holiday rental accommodation in Winter Park?
The most desirable types of holiday rentals in Winter Park are condos. Prefer something different? Vrbo has numerous options to match our guests' unique requirements, so you'll see holiday homes in loads of sizes and shapes. The perfect fit is waiting for you — book yours today.
How much does it cost to rent a holiday rental in Winter Park?
Different factors affect the price of a holiday rental in Winter Park, such as the time of year, length of stay and property type. However, all our holiday homes have something in common — exceptional value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Winter Park?
When you travel and the style and size of the property will determine the cost of your beachside escape. Put in your Winter Park travel dates to see your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your holiday home.
Are there pet-friendly holiday rentals in Winter Park?
Pack a travel bag and a bone for the pup in your life because Winter Park has 598 stays that open their doors to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Winter Park?
Tick the "pool" box in our handy filter tool and select from 255 houses with private pools in Winter Park on Vrbo. Ball games, gentle soak or noodle joust? Free time is up to you when your Vrbo holiday home comes with a swimming pool.
What are popular rental amenities in Winter Park?
Some of the most popular rental amenities guests are looking for in Winter Park are tennis, a chef and a lake view. Whether you're travelling with family, buddies or even pets, Vrbo holiday properties feature the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday rentals in Winter Park?
Winter Park has 101 holiday properties that can fit 10 or more people. These properties come with the space and privacy you need to share good times with your nearest and dearest.
Are there holiday rentals in Winter Park that welcome kids?
With 598 family-friendly holiday rentals available in Winter Park, now is a fantastic time to introduce your children to the pleasures of travel. Simply check our "Properties good for families" filter box to view stays packed with amenities perfect for families on the move, such as multiple bedrooms, yards, bunk beds and entertainment areas.
What are the top attractions for families in Winter Park?
There are plenty of amazing things to see and do with the family in Winter Park, including:
  • Amazen Maze Winter Park
  • Moffat Tunnel West Portal
  • Trestle Bike Park
Are there one-bedroom holiday rentals in Winter Park?
You'll find 106 one-bedroom properties in Winter Park to choose from. A one-bedroom holiday home is a wonderful choice if it's just you and your partner or if you're holidaying alone. Toss in more convenience, space and privacy compared to a hotel, and you're bound to have a memorable trip.
Can I find two-bedroom holiday rentals in Winter Park?
Gather your nearest and dearest and enjoy peace, privacy and comfort in one of the 221 two-bedroom holiday properties Winter Park has to offer.
Are there holiday rentals with WiFi in Winter Park?
Whether you want to keep up with the headlines, reply to emails or surf your social networks, there are 157 holiday homes with WiFi in Winter Park. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Winter Park?
You can pick from 27 Vrbo holiday homes with air conditioning in Winter Park giving you that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then use our filter tool to search for stays with air conditioning.
How old do you have to be to rent a holiday rental in Winter Park?
We recommend checking with the Winter Park holiday rental you'd like on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Winter Park for?
How long you can rent a holiday rental in Winter Park is down to the property. Simply enter your chosen travel dates to look at a list of options offering extended stays. With loads of amenities like laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get somewhere just right to call your home away from home in Winter Park.

More holiday ideas