50 Best Winter Park Apartments on Holiday Lettings - Condos

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157 Vacation rentals

(82) Excellent 

22

Vacation apartment accommodation

Grand County / Winter Park

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
Rent this remodeled two-bedroom two-bath condo on the upper west side of the Town of Winter Park for just $159 Fri/Sat night or $119/night other nights during the ski season (it's a bit more during Spring Break and a lot less before Dec. 10th)! Minimum of 3 nights & si …see more

from $89 / night

$549 - $776 / week

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from $89 / night

(2) Excellent 

24

Winter Park ski condo to rent.

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ski
  • Child friendly
Brand new, beautifully decorated, well equipped, spacious and open, 1,300+ square foot condo at Trailhead Lodge in the heart of Winter Park! Close to everything Winter Park has to offer! .......... …see more

from $165 / night

$1155 / week

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from $165 / night

(8) Excellent 

27

Winter Park ski apartment to rent.

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 …see more

from $129 / night

$1943 / week

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from $129 / night

(1) Excellent 

23

Winter Park ski condo to rent.

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ski
  • Child friendly
This is a super cozy and elegant 2 bedroom/2 bathroom, over 1200 square foot condo with everything you need right at your finger tips, conveniently located 1/3 of a mile from Winter Park Resort. The living room is a place where you can relax and "melt," with a warm fire …see more

from $149 / night

$1043 / week

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from $149 / night

(3) Very Good 

28

Winter Park Vacation home rental

Grand County / Winter Park

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
This beautiful, unique home home boasts three levels of high end wood furnishings and a modern, rustic feel for a perfect mountain getaway. Relax on the expansive private deck, complete with with forest views, gas fire pit table and grill, or cozy up in front of the two …see more

from $467 / night

$3269 / week

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from $467 / night

(7) Excellent 

30

Winter Park ski condo to rent.

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 …see more

from $129 / night

$1943 / week

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from $129 / night

(1) Excellent 

4

Vacation condo in Winter Park

Grand County / Winter Park

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Great deal on a fully-furnished downtown Winter Park condo in the Hi Country Haus condo complex This condo in the High Country Haus complex is newly remodeled. One of the best features is that it is only a block off Main Street - some of the best restaurants and bars …see more

from $90 / night

$530 / week

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from $90 / night

(32) Excellent 

31

Vacation home in Winter Park

Grand County / Winter Park

5 19 Min stay varies

  • 5 bedrooms
  • Sleeps 19
  • Min stay varies
  • Child friendly
With high-end finishes throughout the home, including granite countertops and vaulted ceilings, Elk Lodge is the epitome of luxury and comfort. Dine al fresco on the large porch with a sizeable gas grill, or cozy up in front of the fireplace with hot cocoa. Enjoy a priv …see more

from $414 / night

$2898 / week

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from $414 / night

33

Winter Park Vacation apartment rental

Grand County / Winter Park

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
Have the ultimate Rocky Mountain getaway by staying at this charming Winter Park vacation rental condo, ideally situated within close proximity of Winter Park Ski Resort, Rocky Mountain National Park, restaurants, and more.  With 1 bedroom, 1 bathroom, and enough room …see more

from $99 / night

$693 - $1365 / week

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from $99 / night

(18) Very Good 

32

Vacation home in Winter Park

Grand County / Winter Park

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
Vaulted ceilings over picture windows with incredible views, a full kitchen, large dining area and a separate breakfast bar, plus tons of places to sleep or relax- just a few of the many perks of this beautiful Vasquez Retreat home. With comfortable leather furniture an …see more

from $450 / night

$3150 / week

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from $450 / night

(15) Very Good 

25

Vacation home in Winter Park

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This new corner condo offers the benefit of incredible views of both the mountains and the Village walk. With new, tasteful decor and easy access to the amenity deck (with hot tub, outdoor fireplace, and grill), this is a peaceful mountain home that offers the convenien …see more

from $185 / night

$1295 / week

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from $185 / night

(2) Excellent 

34

Vacation home in Winter Park

Grand County / Winter Park

4 16 Min stay varies

  • 4 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
Welcome to the HGTV 2007 Dream Home!  Tucked away in the secluded Bridger's Cache neighborhood below the Mary Jane slopes, this luxurious yet delightfully welcoming home has all the trappings you would expect of its coveted title.  Enjoy classic mountain architecture wi …see more

from $459 / night

$3213 / week

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from $459 / night

(4) Excellent 

31

Winter Park ski condo to rent.

Grand County / Winter Park

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 …see more

from $119 / night

$1783 / week

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from $119 / night

(11) Very Good 

28

Vacation home in Winter Park

Grand County / Winter Park

4 15 Min stay varies

  • 4 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
With a unique layout and high-end finishes, including granite countertops, expertly crafted woodwork, and two wet bars, this mountain escape is the epitome of relaxation. Tall windows with incredible mountain views, and beautiful decor give this place an air of luxury. …see more

from $398 / night

$2786 / week

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from $398 / night

(3) Excellent 

43

Winter Park ski apartment to rent.

Grand County / Winter Park

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
Completely remodeled RIVERFRONT SUITE with high end custom finishes! At the base of Winter Park Ski Resort! This ground level condo is located in Winter Park Place, a small private complex nestled in the trees and backing to the beautiful Fraser River in Old Town Winte …see more

from $150 / night

$975 - $3500 / week

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from $150 / night

(2) Excellent 

33

Winter Park Vacation home rental

Grand County / Winter Park

7 30 Min stay varies

  • 7 bedrooms
  • Sleeps 30
  • Min stay varies
  • Child friendly
This beautiful home has just been fully remodeled from top to bottom with customized touches, unique hand-made furnishings, and a floor plan tailored to accommodate large families and groups on their mountain getaway. The spoils begin before you even enter the home with …see more

from $668 / night

$4676 / week

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from $668 / night

23

Ski home to rent in Winter Park

Grand County / Winter Park

5 17 3 nights min

  • 5 bedrooms
  • Sleeps 17
  • 3 nights min
  • Ski
  • Child friendly
This 5 bedroom / 6 bath house sleeps 17 people! Located only a few hundred meters from the ski lifts, this uniquely decorated house is nestled in the pines with spectacular views of the continental divide. Relax in the 6 person hot tub after a day of skiing at one of Co …see more

from $500 / night

$3500 / week

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from $500 / night

(3) Very Good 

17

Apartment rental in Winter Park with shared pool

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
2 bedroom, 1.25 bathroom, quiet, top floor end unit. Great for families looking for affordability and easy access to amenities. Front-loading washer and dryer in unit. Next to clubhouse with pool, hot tubs and a rec center. Sledding hill, playground, restaurants and bak …see more

from $100 / night

$600 - $1380 / week

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from $100 / night

(21) Very Good 

33

Vacation home in Winter Park

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
An exquisite place to host large family getaways, this ski-in/ski-out property is the only 4-bedroom condo right at the Winter Park base. The space features two distinctive and comfortable living areas with plenty of room to spread out. This exclusive property is locate …see more

from $350 / night

$2450 / week

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from $350 / night

(24) Very Good 

27

Home rental in Winter Park

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
With plenty of seating for large gatherings, this open floor plan is the perfect place for conversation and comfort. Every detail is in place to indulge your senses: a chef's kitchen for producing gourmet delights, two living areas for unwinding and socializing. Lots of …see more

from $398 / night

$2786 / week

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from $398 / night

(1) Excellent 

26

Winter Park Vacation home rental

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Welcome to Alpine Hollow! Experience the Colorado Rocky Mountains like never before from this warm and inviting home, well-situated for the many year-round activities Winter Park has to offer! With 4 bedrooms, 3 bathrooms, and 2 living areas spread over 3 levels, it com …see more

from $260 / night

$1820 - $6643 / week

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from $260 / night

25

Vacation home rental

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
With incredible views of the Continental Divide, this home is the ultimate in mountain living. With a two-story wood-burning fireplace, you can relax and enjoy this majestic setting in comfort and luxury. With over 2,745 square feet and an enormous living room, this is …see more

from $424 / night

$2968 / week

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from $424 / night

(3) Very Good 

20

Vacation condo with shared pool in Winter Park

Grand County / Winter Park

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
Welcome to our bright remodeled 2nd floor end unit at Beaver Village located in the town of Winter Park, Colorado. Beaver Village Condominiums are a perfect in town location, surrounded by acres of tree studded hills and features decks for nature viewing and relaxation. …see more

from $125 / night

$875 / week

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from $125 / night

(1) Excellent 

24

Winter Park Vacation home rental

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Gather your loved ones for the ultimate getaway to Winter Park, Colorado when you book this 3-bedroom, 3-bathroom vacation rental house, which sleeps 8. With gorgeous mountain views right from the spacious front porch and various hiking and biking trails throughout the …see more

from $174 / night

$1044 - $3145 / week

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from $174 / night

31

Home rental in Winter Park

Grand County / Winter Park

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
This spacious home easily accommodates several families with plenty of private sleeping room, and large, relaxing gathering areas.This space features a private hot tub, deluxe comfortable furniture, and a spacious great room with fireplace and large flat screen TV for g …see more

from $422 / night

$2954 / week

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from $422 / night

(23) Excellent 

27

Vacation home in Winter Park

Grand County / Winter Park

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
In this stunning, inviting and airy retreat you can find yourself completely at ease. The open floor plan and cathedral ceilings showcase magnificent high-end finishes throughout the home. The large wraparound porch houses a hot tub, a great place to soak and enjoy the …see more

from $402 / night

$2814 / week

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from $402 / night

(1) Excellent 

22

Winter Park ski condo to rent.

Grand County / Winter Park

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 1 …see more

from $99 / night

$1143 / week

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from $99 / night

26

Vacation apartment in Winter Park

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
Whether you’re looking for a relaxing alpine getaway or for a vacation full of thrilling adventures on snow-capped peaks, there’s no better destination for a mountain retreat than Winter Park, Colorado. Boasting beautiful rivers, coveted ski slopes, pristine hiking trai …see more

from $99 / night

$693 - $1603 / week

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from $99 / night

36

Vacation home in Winter Park

Grand County / Winter Park

4 15 Min stay varies

  • 4 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
Looking for the seclusion of a private home, but not willing to sacrifice being close to downtown restaurants, shops, and the slopes? Look no further than Moose Crossing Cabin. With frequent moose and other wildlife sightings, a newly remodeled kitchen and outdoor patio …see more

from $424 / night

$2968 / week

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from $424 / night

(6) Excellent 

19

Ski home to rent in Winter Park

Grand County / Winter Park

3 12 2 nights min

  • 3 bedrooms
  • Sleeps 12
  • 2 nights min
  • Ski
  • Child friendly
With a 2 block walk into the town of Winter Park and backing onto an open meadow, this private mountain home offers wilderness views and proximity to restaurants, shops, and bars in town. Just a few blocks from summer festivities in the park. 1 block from the ski sh …see more

from $195 / night

$1200 - $2600 / week

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from $195 / night

(5) Excellent 

22

Winter Park ski condo to rent.

Grand County / Winter Park

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 1 …see more

from $99 / night

$1143 / week

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from $99 / night

(3) Excellent 

23

Home rental in Winter Park

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Enjoy beautiful, high end mountain furnishings and amenities when you stay at this three level townhome overlooking Downtown Winter Park.  Large picture windows light up the main living area and open up spectacular views of the valley and mountains all along the Contine …see more

from $271 / night

$1897 / week

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from $271 / night

(2) Excellent 

26

Winter Park ski condo to rent.

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 …see more

from $129 / night

$1943 / week

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from $129 / night

(1) Excellent 

26

Vacation home in Winter Park

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Located above downtown Winter Park, the Bear Crossing Townhome has everything you want for an unforgettable mountain getaway. Boasting two living areas, this townhome is perfect for families or groups wanting to be together with some room to spread out. Enjoy the privat …see more

from $213 / night

$1491 / week

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from $213 / night

(34) Very Good 

24

Home rental in Winter Park

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
This bright condo is right in the mix, a short walk to the lifts and the Village at Winter Park Resort.  Relax by the fire while watching skiers fly down the mountain, or kick back with a book on exquisite living room furniture. Bonus tip: the balcony overlooks the amen …see more

from $118 / night

$826 / week

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from $118 / night

(4) Excellent 

24

Winter Park Vacation home rental

Grand County / Winter Park

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
Ascend into a piece of paradise in this beckoning mountain home nestled amongst the trees. You will relax in quiet warmth with views of the peaks; yet a mere one stop away on the free resort shuttle, is the bustle of activity at Winter Park Village. After a day of activ …see more

from $253 / night

$1771 / week

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from $253 / night

(27) Very Good 

27

Home rental in Winter Park

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
The fun and welcoming decor in this updated Zephyr condo pays homage to the snowy slopes outside, which you can be skiing on in seconds! Enjoy all the best amenities including flat screen TVs in all the bedrooms, a fully equipped kitchen, views of the ski trails and a f …see more

from $185 / night

$1295 / week

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from $185 / night

27

Vacation home in Winter Park

Grand County / Winter Park

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
The décor of this magnificent mountain home will leave you feeling absolutely spoiled.  Each room is expertly designed with both comfort and aesthetic in mind, from the incredibly beautiful chandelier over the dining table, to the elegant stone and woodwork throughout t …see more

from $327 / night

$2289 / week

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from $327 / night

(9) Very Good 

28

Winter Park Vacation home rental

Grand County / Winter Park

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Nestled in the heart of Base Camp, this luxury townhome exudes relaxation and high-end touches. Earlybirds can enjoy the sunrise over the forest from the east-facing deck, or the kitchen-adjacent opposite deck offers a soothing place to enjoy a soak in the hot tub. Mult …see more

from $398 / night

$2786 / week

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from $398 / night

26

Winter Park Vacation home rental

Grand County / Winter Park

3 11 Min stay varies

  • 3 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
This rare Base Village Loft boasts a unique floor plan all on one level! This beautiful space sits perched directly above the Village walk and is just steps away from dining, nightlife, outdoor activities, and a few minutes walk to the Zephyr lift. Beautiful wood and st …see more

from $276 / night

$1932 / week

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from $276 / night

1