Photo by Winter Park Resort

Winter Park holiday rentals

We found 2,018 holiday rentals — enter your dates for availability
Select from 341 houses, 479 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:1 Jan - 8 Jan

Living area
Private kitchen
Room
Interior
Exceptional
(17 reviews)

Cozy mountain escape in Empire

Empire

7% off
S$2,696
for 7 nights, 1 home
S$385 per night
includes taxes & fees
Cozy mountain escape in Empire
Wild West Suite's private office area, fireplace and sitting room.
The Wild West suite - private bath, sitting area, fireplace, and office area
Formal Dining Area of Great Room
Looking up at the back of Oso's from private road below, in the fall
Exceptional
(52 reviews)

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

Winter Park

8% off
S$13,148
for 7 nights, 1 home
S$1,878 per night
includes taxes & fees
7 Acre Mountain Retreat: 7 bdrms 7.5 ba gourmet kitchen; ski raft hike fish bike
Welcome to your mountain getaway!
Over-sized kitchen island for easy meal prep and serving
Gourmet Kitchen
View from Living Room window
Exceptional
(240 reviews)

5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle

Winter Park

11% off
S$10,172
for 7 nights, 1 home
S$1,453 per night
includes taxes & fees
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
Exterior detail
Private kitchen
Pool
Living area
Exceptional
(46 reviews)

Dog-friendly condo close to Winter Park shuttle with pool, hot tub, tennis, gym

Fraser

8% off
S$3,374
for 7 nights, 1 apartment
S$482 per night
includes taxes & fees
Dog-friendly condo close to Winter Park shuttle with pool, hot tub, tennis, gym
Exterior
Exterior
Dining
Room
Exceptional
(71 reviews)

Winter Park Retreat - In The Heart Of Downtown

Winter Park

7% off
S$8,376
for 7 nights, 1 home
S$1,197 per night
includes taxes & fees
Winter Park Retreat - In The Heart Of Downtown
Mary Jane Trail top
Property grounds
Clubhouse
Dining and kitchen
Exceptional
(82 reviews)

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

Winter Park

8% off
S$5,522
for 7 nights, 1 apartment
S$789 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
Interior
Exceptional
(28 reviews)

Penthouse Cozy Condo in the heart of Downtown Winter Park

Winter Park

8% off
S$5,742
for 7 nights, 1 apartment
S$820 per night
includes taxes & fees
Penthouse Cozy Condo in the heart of Downtown Winter Park
Dining
Private kitchen
Living area
Property grounds
Exceptional
(6 reviews)

Family-Friendly Remodeled Condo in Downtown Fraser

Fraser

11% off
S$2,828
for 7 nights, 1 apartment
S$404 per night
includes taxes & fees
Family-Friendly Remodeled Condo in Downtown Fraser
Room
Living area
The view of Vasquez Territory at Winter Park from just out the front door.
Private kitchen
Exceptional
(83 reviews)

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

Winter Park

7% off
S$5,474
for 7 nights, 1 home
S$782 per night
includes taxes & fees
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Bedroom with king size bed and views of the mountains.
ZML Riverside building
1 of 4 hot tubs in Slopeside and Riverside buildings
Living room with queen sleeper sofa and views.
Exceptional
(30 reviews)

Zephyr Mountain Lodge - Beautifully Renovated

Winter Park

8% off
S$5,733
for 7 nights, 1 apartment
S$819 per night
includes taxes & fees
Zephyr Mountain Lodge - Beautifully Renovated
Capture the mountain view from the kitchen. Great socializing lay out!
Enjoy the sunset from the private back deck.
Unit perched on the top floor with spectacular views and privacy!
Huge great room to socialize with family and friends
Exceptional
(57 reviews)

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

Fraser

11% off
S$5,517
for 7 nights, 1 apartment
S$788 per night
includes taxes & fees
Gorgeous luxury top floor condo! Stunning Mountain Views! Private decks! Garage
Dining table fits 6 and has a leaf for expansion. Folding chairs available
Open concept kitchen, dining, living
Toasty gas fireplace for snowy nights. Smart TV with DVD player and board games
Main living area with forest views.
Exceptional
(5 reviews)

3 BR Penthouse- Walk to town- Last stop on free bus to resort- Family friendly!

Winter Park

7% off
S$3,979
for 7 nights, 1 apartment
S$568 per night
includes taxes & fees
3 BR Penthouse- Walk to town- Last stop on free bus to resort- Family friendly!
Welcome to Trademark, three blocks from the base of Winter Park!
Living Room with spectacular views, 50' flat screen HD-TV and free WIFI.
Dining room with seating for 10
Gourmet kitchen
Exceptional
(47 reviews)

Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark

Winter Park

11% off
S$6,701
for 7 nights, 1 apartment
S$957 per night
includes taxes & fees
Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark
Private kitchen
Private kitchen
Interior
Interior
Exceptional
(84 reviews)

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

Dumont

8% off
S$2,121
for 7 nights, 1 home
S$303 per night
includes taxes & fees
Adorable Cottage in National Forest -- hiking & climbing steps from your door!
kitchen
Terrace/patio
Exterior
Main floor family room
Exceptional
(6 reviews)

Scenic Luxury Townhouse next to Winter Park Resort

Fraser

8% off
S$4,247
for 7 nights, 1 home
S$607 per night
includes taxes & fees
Scenic Luxury Townhouse next to Winter Park Resort
Living area
Kitchen with induction cooktop
Room
View of Slopes
Exceptional
(56 reviews)

Two Free E-bikes included. Walk to base. Inside the WP gates. Private hot tub.

Winter Park

8% off
S$6,657
for 7 nights, 1 home
S$951 per night
includes taxes & fees
Two Free E-bikes included. Walk to base. Inside the WP gates. Private hot tub.
Living room with large TV, queen sleeper and walk-out access to private hot tub
Interior
Outdoor spa tub
Fully appointed kitchen with all you will need to prepare meals and eat in.
Exceptional
(21 reviews)

Heart of Downtown - Private Hot Tub, Heated Garage, Fireplace & Washer/Dryer

Winter Park

8% off
S$3,014
for 7 nights, 1 apartment
S$431 per night
includes taxes & fees
Heart of Downtown - Private Hot Tub, Heated Garage, Fireplace & Washer/Dryer
Rec Center Game Room
Rec Center sitting area w/ TV
Rec Center deck w/ outdoor hottub
Rec Center Workout room
Exceptional
(31 reviews)

Cozy 1 Bedroom Hi Country Haus - on river !

Winter Park

8% off
S$2,121
for 7 nights, 1 apartment
S$303 per night
includes taxes & fees
Cozy 1 Bedroom Hi Country Haus - on river !
Mudroom
Spacious, well-appointed kitchen
Master with king-size bed
TV room
Exceptional
(87 reviews)

Renovated, steps to restaurants, mountain views, on free bus route

Winter Park

7% off
S$2,469
for 7 nights, 1 apartment
S$353 per night
includes taxes & fees
Renovated, steps to restaurants, mountain views, on free bus route
FullSizeRender
IMG_4694
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Exceptional
(16 reviews)

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

Winter Park

5% off
S$7,068
for 7 nights, 1 apartment
S$1,010 per night
includes taxes & fees
New Luxury 3-Bedroom Condo 1/2 Block to Main St
remodeled kitchen with stainless steel appliances, marble counter tops and gas
Living area
Interior
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$6,796
for 7 nights, 1 home
S$971 per night
includes taxes & fees
Private Mountain Home. Hot Tub. Dog-Friendly. 10 Min to Winter Park Resort

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  • 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)
  • Keystone Ski Resort (25.5 mi / 41.1 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)

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)
  • 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)
  • Loveland Pass (18.4 mi / 29.6 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