Photo by Winter Park Resort

Winter Park holiday rentals

We found 2,040 holiday rentals — enter your dates for availability
Select from 327 houses, 501 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:20 Nov - 27 Nov

Living area
Terrace/patio
Private kitchen
Living area
Exceptional
(52 reviews)

Lake Front Cabin With Mountain Views & Direct Access to Fishing

Idaho Springs

8% off
S$5,534
for 7 nights, 1 home
S$791 per night
includes taxes & fees
Lake Front Cabin With Mountain Views & Direct Access to Fishing
Interior
Exterior
Bar (on property)
Private kitchen
Wonderful
(22 reviews)

Large Upscale Retreat off Vasquez Rd. Sleeps 14

Winter Park

11% off
S$8,524
for 7 nights, 1 cabin
S$1,218 per night
includes taxes & fees
Large Upscale Retreat off Vasquez Rd. Sleeps 14
Room
Kitchen
Private outdoor hot tub
Living room and Fireplace
Exceptional
(5 reviews)

Secluded and cozy 3 BR Duplex in Winter Park

Winter Park

10% off
S$4,126
for 7 nights, 1 home
S$589 per night
includes taxes & fees
Secluded and cozy 3 BR Duplex in Winter Park
Living area
Terrace/patio
Exterior
Room
Exceptional
(33 reviews)

Beautiful view 2 miles above sea level

Idaho Springs

8% off
S$2,017
for 7 nights, 1 home
S$288 per night
includes taxes & fees
Beautiful view 2 miles above sea level
Exterior
Exterior
Dining
Living room
Exceptional
(71 reviews)

Winter Park Retreat - In The Heart Of Downtown

Winter Park

7% off
S$4,343
for 7 nights, 1 home
S$620 per night
includes taxes & fees
Winter Park Retreat - In The Heart Of Downtown
Private kitchen
Living area
Interior
The view of Vasquez Territory at Winter Park from just out the front door.
Exceptional
(79 reviews)

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

Winter Park

7% off
S$3,224
for 7 nights, 1 home
S$461 per night
includes taxes & fees
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Interior
Private kitchen
Interior
Private kitchen
Exceptional
(79 reviews)

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

Dumont

8% off
S$2,122
for 7 nights, 1 home
S$303 per night
includes taxes & fees
Adorable Cottage in National Forest -- hiking & climbing steps from your door!
Welcome to Trademark, three blocks from the base of Winter Park!
Living Room with spectacular views, 50' flat screen HD-TV and free WIFI.
Shared hot tub right out the front door
Gourmet kitchen
Exceptional
(47 reviews)

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

Winter Park

11% off
S$5,163
for 7 nights, 1 apartment
S$738 per night
includes taxes & fees
Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark
Living area
Kitchen with induction cooktop
Interior
Room
Exceptional
(56 reviews)

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

Winter Park

7% off
S$3,389
for 7 nights, 1 home
S$484 per night
includes taxes & fees
Two Free E-bikes included. Walk to base. Inside the WP gates. Private hot tub.
Great room with views of the mountains
Great Room with fireplace & Samsung TV - Sonos Bar
8-person hot tub facing southwest
Kitchen with an island & dining table.
Exceptional
(134 reviews)

Beautiful Mountain Home-Great Views-Hot Tub-Free Resort Shuttle-Toddler Friendly

Fraser

7% off
S$3,413
for 7 nights, 1 cabin
S$488 per night
includes taxes & fees
Beautiful Mountain Home-Great Views-Hot Tub-Free Resort Shuttle-Toddler Friendly
Barstool seating at kitchen counter
Private hot tub- enjoy the beautiful ambiance of the patio with fire pit table
Spacious kitchen and dining area with room to mingle
Elk Creek Condos Bldg C
Exceptional
(27 reviews)

Bonus Bunk Room! Private Hot Tub and Walkable to Restaurants and Brewery!

Fraser

7% off
S$3,367
for 7 nights, 1 apartment
S$481 per night
includes taxes & fees
Bonus Bunk Room! Private Hot Tub and Walkable to Restaurants and Brewery!
Work area in kitchen has seating, great outdoor and indoor views
Exterior Winter shot of the townhome
New Bullfrog hot tub in private entry courtyard
Looking out from the DR to the Great Room and kitchen with massive sunlight
Exceptional
(87 reviews)

A Winter Park Gem - Reserve this Gorgeous Townhome Early

Winter Park

10% off
S$3,574
for 7 nights, 1 home
S$511 per night
includes taxes & fees
A Winter Park Gem - Reserve this Gorgeous Townhome Early
Mudroom
Spacious, well-appointed kitchen
TV room
Entrance
Exceptional
(87 reviews)

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

Winter Park

7% off
S$2,506
for 7 nights, 1 apartment
S$358 per night
includes taxes & fees
Renovated, steps to restaurants, mountain views, on free bus route
Living area
Exterior
Living area
Dining
Exceptional
(7 reviews)

Secluded family-friendly condo a minute from ski shuttle and trailheads

Winter Park

8% off
S$2,013
for 7 nights, 1 apartment
S$288 per night
includes taxes & fees
Secluded family-friendly condo a minute from ski shuttle and trailheads
Private kitchen
Room
Interior
Property grounds
Exceptional
(15 reviews)

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

Winter Park

8% off
S$4,306
for 7 nights, 1 apartment
S$615 per night
includes taxes & fees
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Interior
Kitchen into Living Spaces
Dining & Kitchen
Open Floor Plan Living, Dining, Kitchen
Exceptional
(28 reviews)

Penthouse Cozy Condo in the heart of Downtown Winter Park

Winter Park

8% off
S$3,810
for 7 nights, 1 apartment
S$544 per night
includes taxes & fees
Penthouse Cozy Condo in the heart of Downtown Winter Park
Room
Lobby
Living area
Pool
Exceptional
(146 reviews)

Ski-in Ski-out studio

Winter Park

7% off
S$1,329
for 7 nights, 1 apartment
S$190 per night
includes taxes & fees
Ski-in Ski-out studio
Pool and indoor hot tub at the Recreation Center.
Recreation Center, outdoor hot tub
Gym at the Recreation Center.
Swim spa at the recreation center.
Wonderful
(60 reviews)

Cozy, 1 bedroom Condo, 2 Blocks from Downtown, on Ski Bus Route

Winter Park

10% off
S$1,578
for 7 nights, 1 apartment
S$225 per night
includes taxes & fees
Cozy, 1 bedroom Condo, 2 Blocks from Downtown, on Ski Bus Route
Living room with queen sleeper sofa and views.
ZML Riverside building
1 of 4 hot tubs in Slopeside and Riverside buildings
Lodge lobby
Exceptional
(30 reviews)

Zephyr Mountain Lodge - Beautifully Renovated

Winter Park

8% off
S$4,043
for 7 nights, 1 apartment
S$578 per night
includes taxes & fees
Zephyr Mountain Lodge - Beautifully Renovated
View of private patio looking out over the mountains and downtown Winter Park.
Sunset view overlooking Cooper Creek Square from Condo Building
2 Guest Hot Tubs to soak in after your mountain adventures!
Completely remodeled kitchen.
Exceptional
(6 reviews)

Luxe Downtown Winter Park Condo + Hot Tubs - 3 Full Baths - Steps to Shuttle

Winter Park

7% off
S$2,043
for 7 nights, 1 apartment
S$292 per night
includes taxes & fees
Luxe Downtown Winter Park Condo + Hot Tubs - 3 Full Baths - Steps to Shuttle
Exterior
Room
Private kitchen
Terrace/patio
Exceptional
(11 reviews)

Modern/Rustic 2-bedroom Townhouse + Bonus Loft

Winter Park

7% off
S$2,283
for 7 nights, 1 home
S$326 per night
includes taxes & fees
Modern/Rustic 2-bedroom Townhouse + Bonus Loft
Exterior
Interior
Golf
Pool
Exceptional
(99 reviews)

A cozy non-smoking condo on the Fraser River in downtown Winter Park.

Winter Park

7% off
S$1,402
for 7 nights, 1 apartment
S$200 per night
includes taxes & fees
A cozy non-smoking condo on the Fraser River in downtown Winter Park.
Mary Jane Trail top
Property grounds
Dining and kitchen
Pool and hot tub at the clubhouse
Exceptional
(82 reviews)

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

Winter Park

7% off
S$3,006
for 7 nights, 1 apartment
S$429 per night
includes taxes & fees
Luxury condo, Pool and Hot Tub, Ski Shuttle, Downtown, Close to All!
Indoor/outdoor heated pool.
Gas firepit on pool deck to add to the relaxed ambience.
Lobby common area with gas fireplace and plenty of seating.
Common sitting area on the pedestrian bridge connecting building D and C.
Exceptional
(37 reviews)

Top floor unit on The Corridor! AC Unit - 5 min. walk to WP Base! Pool-Hot Tub!

Winter Park

8% off
S$1,689
for 7 nights, 1 apartment
S$241 per night
includes taxes & fees
Top floor unit on The Corridor! AC Unit - 5 min. walk to WP Base! Pool-Hot Tub!

  • 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)
  • 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)
  • Loveland Ski Area (17.5 mi / 28.2 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