Photo by Winter Park Resort

Winter Park holiday rentals

We found 2,013 holiday rentals — enter your dates for availability
Select from 327 houses, 490 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:6 Nov - 13 Nov

Interior
Exterior
Bar (on property)
Private kitchen
Wonderful
(22 reviews)

Large Upscale Retreat off Vasquez Rd. Sleeps 14

Winter Park

11% off
S$7,664
for 7 nights, 1 cabin
S$1,095 per night
includes taxes & fees
Large Upscale Retreat off Vasquez Rd. Sleeps 14
Room
Exterior
Dining
Exterior
Exceptional
(71 reviews)

Winter Park Retreat - In The Heart Of Downtown

Winter Park

7% off
S$3,261
for 7 nights, 1 home
S$466 per night
includes taxes & fees
Winter Park Retreat - In The Heart Of Downtown
Interior
Living area
Private kitchen
Room
Exceptional
(79 reviews)

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

Winter Park

7% off
S$2,600
for 7 nights, 1 home
S$371 per night
includes taxes & fees
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Interior
View of dining, kitchen, and living room area.
Kitchen with stools for additional seating, new appliances, and a large pantry
Exceptional
(100 reviews)

Slopeside Paradise--3 BR, 2.5 Bath 2 Minutes from the Slopes!

Winter Park

7% off
S$4,988
for 7 nights, 1 home
S$713 per night
includes taxes & fees
Slopeside Paradise--3 BR, 2.5 Bath 2 Minutes from the Slopes!
Welcome to Trademark, three blocks from the base of Winter Park!
Living Room with spectacular views, 50' flat screen HD-TV and free WIFI.
Gourmet kitchen
Shared hot tub right out the front door
Exceptional
(47 reviews)

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

Winter Park

10% off
S$3,895
for 7 nights, 1 apartment
S$556 per night
includes taxes & fees
Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark
Living area and kitchen peninsula with stools
View from kitchen to living and dining area, including door to balcony
Open concept living and dining with great views!
Shared external party area with shared hot tub, pool, grill &outdoor fireplace
Exceptional
(24 reviews)

Modern Luxury Condo 3bed/2bath Ski In/Ski Out - Great for Families

Winter Park

8% off
S$13,773
for 7 nights, 1 apartment
S$1,968 per night
includes taxes & fees
Modern Luxury Condo 3bed/2bath Ski In/Ski Out - Great for Families
Another loft view looking out to the outdoor deck
Exterior Winter shot of the townhome
New Bullfrog hot tub in private entry courtyard
Work area in kitchen has seating, great outdoor and indoor views
Exceptional
(86 reviews)

A Winter Park Gem - Reserve this Gorgeous Townhome Early

Winter Park

10% off
S$3,351
for 7 nights, 1 home
S$479 per night
includes taxes & fees
A Winter Park Gem - Reserve this Gorgeous Townhome Early
TV room
Spacious, well-appointed kitchen
Master with king-size bed
Mudroom
Exceptional
(85 reviews)

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

Winter Park

7% off
S$2,480
for 7 nights, 1 apartment
S$354 per night
includes taxes & fees
Renovated, steps to restaurants, mountain views, on free bus route
Property grounds
Room
Private kitchen
Interior
Exceptional
(15 reviews)

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

Winter Park

8% off
S$4,344
for 7 nights, 1 apartment
S$621 per night
includes taxes & fees
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Room
Lobby
Living area
Pool
Exceptional
(144 reviews)

Ski-in Ski-out studio

Winter Park

7% off
S$1,342
for 7 nights, 1 apartment
S$192 per night
includes taxes & fees
Ski-in Ski-out studio
Deck
Kitchen into Living Spaces
Interior
Dining & Kitchen
Exceptional
(28 reviews)

Penthouse Cozy Condo in the heart of Downtown Winter Park

Winter Park

8% off
S$3,535
for 7 nights, 1 apartment
S$505 per night
includes taxes & fees
Penthouse Cozy Condo in the heart of Downtown Winter Park
Outdoor spa tub
Exterior
Private kitchen
Private kitchen
Exceptional
(98 reviews)

Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...

Winter Park

7% off
S$3,630
for 7 nights, 1 home
S$519 per night
includes taxes & fees
Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...
Recreation Center Fire Place and TV
Recreation Center, outdoor hot tub
Swim spa at the recreation center.
Pool and indoor hot tub at the Recreation Center.
Wonderful
(59 reviews)

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

Winter Park

10% off
S$1,267
for 7 nights, 1 apartment
S$181 per night
includes taxes & fees
Cozy, 1 bedroom Condo, 2 Blocks from Downtown, on Ski Bus Route
Interior
Property grounds
Terrace/patio
Living area
Exceptional
(147 reviews)

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

Winter Park

7% off
S$2,380
for 7 nights, 1 apartment
S$340 per night
includes taxes & fees
WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH
Exterior
Interior
Pool
Golf
Exceptional
(98 reviews)

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

Winter Park

7% off
S$1,414
for 7 nights, 1 apartment
S$202 per night
includes taxes & fees
A cozy non-smoking condo on the Fraser River in downtown Winter Park.
Lobby common area with gas fireplace and plenty of seating.
Gas firepit on pool deck to add to the relaxed ambience.
Indoor/outdoor heated pool.
View of the gazebo and fire pit side of the raised pool deck.
Exceptional
(34 reviews)

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

Winter Park

7% off
S$1,108
for 7 nights, 1 apartment
S$158 per night
includes taxes & fees
Top floor unit on The Corridor! AC Unit - 5 min. walk to WP Base! Pool-Hot Tub!
One of the indoor hot tubs at recreation center.
View of the outdoor hot tub at Recreation Center.
Pool and indoor hot tubs at recreation center.
Common area at Recreation center.
Exceptional
(108 reviews)

Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado

Winter Park

10% off
S$1,355
for 7 nights, 1 apartment
S$194 per night
includes taxes & fees
Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado
1 of 4 hot tubs in Slopeside and Riverside buildings
ZML Riverside building
Lodge lobby
Bedroom with king size bed and views of the mountains.
Exceptional
(30 reviews)

Zephyr Mountain Lodge - Beautifully Renovated

Winter Park

7% off
S$2,009
for 7 nights, 1 apartment
S$287 per night
includes taxes & fees
Zephyr Mountain Lodge - Beautifully Renovated
Lobby
Firepit
Inside pool
Ski Bridge from D Building to Corridor Trail
Exceptional
(179 reviews)

Penthouse Studio Ski In-Out- Easy Access Resort; Sauna Pool Gym Hot Tub Views

Winter Park

5% off
S$1,611
for 7 nights, 1 apartment
S$230 per night
includes taxes & fees
Penthouse Studio Ski In-Out- Easy Access Resort; Sauna Pool Gym Hot Tub Views
Indoor pool at clubhouse, plus two indoor hot tubs
Lounge area with large screen TV, pool table, kids area, business center
Beautiful fall leaves from the balcony
Interior
Exceptional
(49 reviews)

Cozy and convenient family condo in heart of downtown Winter Park

Winter Park

7% off
S$2,233
for 7 nights, 1 apartment
S$319 per night
includes taxes & fees
Cozy and convenient family condo in heart of downtown Winter Park
Dining
Property grounds
Fitness facility
Interior
Exceptional
(9 reviews)

Ski in/ski out condo at Winter Park - cozy slopeside with pool, hot tub & more

Winter Park

7% off
S$1,000
for 7 nights, 1 apartment
S$143 per night
includes taxes & fees
Ski in/ski out condo at Winter Park - cozy slopeside with pool, hot tub & more
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

7% off
S$1,428
for 7 nights, 1 apartment
S$204 per night
includes taxes & fees
Cozy 1 Bedroom Hi Country Haus - on river !
Exterior
Hot Tub off of ski run/1st Floor (no jets)
Interior
Pole Creek Golf Course - 20 minute drive from Condo
Exceptional
(8 reviews)

New Condo w/ Hot Tub & Balcony-Short Walk/Bike to Trestle Bike Park & Village

Winter Park

7% off
S$2,755
for 7 nights, 1 apartment
S$394 per night
includes taxes & fees
New Condo w/ Hot Tub & Balcony-Short Walk/Bike to Trestle Bike Park & Village
Dining
Living area
Living area
Pool
Exceptional
(9 reviews)

Updated Condo at Winter Park and Trestle Bike Park

Winter Park

7% off
S$2,423
for 7 nights, 1 apartment
S$346 per night
includes taxes & fees
Updated Condo at Winter Park and Trestle Bike Park

  • 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