50 Best Winter Park Apartments on Holiday Lettings - Condos

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437 Vacation rentals

(6) Very Good 

Certificate of Excellence

11

Ski studio to rent in Winter Park

Grand County / Winter Park

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
True ski-in/ski-out at Winter Park Resort base! This fully updated studio condo is connected to The Corridor ski run (green) that runs between the Mary Jane Territory and the Winter Park base. Unit 2063 sleeps up to four people - 2 adults (queen Murphy bed) and 2 ch …see more

Certificate of Excellence

from $99 / night

$594 - $1,300 / week

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Responds fast!
avg. 2 hours 28 minutes

from $99 / night

18

Vacation condo with shared pool in Winter Park

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
This bright 952 sq. ft. two bedroom two bath condo has been updated and offers all that you need for your vacation. It is nestled in the back of the complex next to the national forest. This is a desirable end unit on the top floor which features vaulted ceilings and ex …see more

from $150 / night

$1,050 / week

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from $150 / night

(7) Excellent 

24

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

$1,943 / week

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Responds fast!
avg. 1 hour 34 minutes

from $129 / night

(6) Excellent 

25

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 $89 / night

$1,143 / week

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Responds fast!
avg. 1 hour 34 minutes

from $89 / night

(1) Excellent 

27

Vacation home in Winter Park

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Comfort and convenience are two words to describe this ski in/out condo. Get on the mountain in just minutes, sit back and relax on the balcony, or stroll through the Village at Winter Park Resort just outside of your door! Sleeping Arrangements: Two queens in the mast …see more

from $167 / night

$1,169 / week

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from $167 / night

(2) Excellent 

24

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

$1,143 / week

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Responds fast!
avg. 1 hour 34 minutes

from $129 / 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 $340 / night

$2,380 - $7,665 / week

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Responds fast!
avg. 39 minutes

from $340 / night

(3) Excellent 

30

Home rental in Winter Park

Grand County / Winter Park

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
This beautiful 3-story townhome sits just above downtown Winter Park, with gorgeous views of the valley and mountains from your large picture windows in the main living area. Enjoy the plush furnishings, high end kitchen, and cozy up by the fireplace after your adventur …see more

from $284 / night

$1,988 / week

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from $284 / night

(1) Excellent 

24

Winter Park Vacation home rental

Grand County / Winter Park

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • 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 that sleeps 7. With gorgeous mountain views right from the spacious front porch, a private hot tub in the breezeway, and several hikin …see more

from $174 / night

$1,044 - $3,144 / week

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Responds fast!
avg. 26 minutes

from $174 / 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 - $1,080 / week

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from $90 / night

(3) Very Good 

33

Home rental in Winter Park

Grand County / Winter Park

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
This exquisite home is located on the third and fourth floors of an exclusive Old Town building (shared only with its sister property, Old Town Loft #1). 2600 square feet of high-end living space, modern amenities, and luxurious furnishings. Group Lodging Option: Large …see more

from $378 / night

$2,646 / week

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from $378 / night

(93) Excellent 

21

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 $99 / night

$599 - $775 / week

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from $99 / night

(6) Very Good 

33

Vacation home rental

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
You'll love the convenience and space provided by this large three bedroom remodeled Zephyr condo. With an ideal set up for couples and small families, this condo has two master suites and three full bathrooms. And, it's situated on the 5th floor of the Slopeside buildi …see more

from $195 / night

$1,365 / week

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from $195 / 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

$949 - $3,550 / week

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Responds fast!
avg. 3 hours 3 minutes

from $150 / night

(3) Very Good 

14

Vacation villa with shared pool in Winter Park

Grand County / Winter Park

4 2 nights min

  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
This studio unit contains a Queen Size Murphy Bed, a futon which folds out and a sofa sleeper. Free WIFI and 32' flatscreen Cable TV. It also has a full kitchen and a full bath. It is very conveniently located within easy walking distance of all restaurants and shops in …see more

from $50 / night

$300 - $750 / week

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Responds fast!
avg. 3 hours 41 minutes

from $50 / night

33

Winter Park Vacation apartment rental

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
Have the ultimate Rocky Mountain getaway by staying at this charming 1-bedroom Winter Park vacation rental condo which sleeps 4. Ideally situated within close proximity of Winter Park Ski Resort, Rocky Mountain National Park, restaurants, and more, this condo ensures an …see more

from $99 / night

$693 - $1,260 / week

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Responds fast!
avg. 53 minutes

from $99 / night

(1) Excellent 

31

Vacation studio in Winter Park

Grand County / Winter Park

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Child friendly
Newly remodeled in the fall of 2017 this condo comes complete with a King bed, a kitchenette, living room & dining room, not to mention the superb location at the base of the ski lift, this Founders Pointe studio has much to offer. Sit by the fireplace or in the huge o …see more

from $103 / night

$721 / week

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from $103 / night

(3) Very Good 

29

Vacation home in Winter Park

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Sit back and watch the skiers fly down the slopes from this perfectly positioned Zephyr condo; or throw on your boots, step out the front door and straight into the action for yourself! Enjoy home cooked meals in the full kitchen, or try one of the many delicious dining …see more

from $118 / night

$826 / week

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from $118 / night

(2) 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

$1,043 / week

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Responds fast!
avg. 55 minutes

from $149 / night

(34) Very Good 

25

Home rental in Winter Park

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Enjoy a new condo right in the center of it all, and only a short stroll to the lifts and the Village at Winter Park Resort. You'll love having the luxury of relaxing by the fire while skiers fly down the mountain just outside your window. This is a fantastic space to r …see more

from $118 / night

$826 / week

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from $118 / night

(53) Very Good 

31

Winter Park Vacation home rental

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Stay in style at the largest and most remodeled Zephyr one bedroom. It's 300 square feet larger than others, at the end of the hallway for quiet evenings, and has a balcony and windows facing the slopes/lifts and then also spans to the other side of the building and be …see more

from $118 / night

$826 / week

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from $118 / night

(27) Very Good 

33

Home rental in Winter Park

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This fun & inviting Zephyr condo has everything a family could want: the perfect ski-in/ski-out location, a fully functional kitchen & flatscreen TVs in all the rooms. Don't feel like playing chef tonight? No problem, pop on your shoes & visit one of the many restauran …see more

from $167 / night

$1,169 / week

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from $167 / night

(1) Excellent 

31

Vacation home with shared pool in Winter Park

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
This brand new building is in one of the most sought after locations in downtown Winter Park. The high end touches and wrap around deck make this property perfect for your mountain getaway! Sleeping Arrangements: King bed in the master, king in the second bedroom, two …see more

from $195 / night

$1,365 / week

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from $195 / night

27

Vacation home in Winter Park

Grand County / Winter Park

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
This townhome has everything you need for your Rocky Mountain getaway. Perfect for groups and families with en suite bathrooms in every bedroom and three floors to spread out. Enjoy the open kitchen, private hot tub with views of the continental divide, and cozy living …see more

from $216 / night

$1,512 / week

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from $216 / night

(4) Excellent 

28

Winter Park Vacation home rental

Grand County / Winter Park

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
Nestled in the trees with views of the peaks and just one shuttle stop away from Winter Park Resort. Unwind in one of the hot tubs or cozy up infront of the rock fireplace. Cook a delicious meal at home in the fully equipped kitchen, or choose from the restaurants close …see more

from $261 / night

$1,827 / week

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from $261 / night

(4) Excellent 

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 - $960 / week

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Responds fast!
avg. 2 hours 53 minutes

from $100 / night

(1) Excellent 

30

Ski studio to rent in Winter Park

Grand County / Winter Park

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly
Condo Corridor is a penthouse STUDIO condo at Iron Horse Resort. Located on the 6th floor of the D Building, on the far end, up against the Mary Jane Corridor Ski Run. Nothing matches the convenience and luxury of a ski/hike/bike FROM/TO to location, especially when yo …see more

from $59 / night

$413 / week

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from $59 / night

(1) Excellent 

25

Vacation home in Winter Park

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Bear Crossing 995 is the perfect spot for families or groups wanting to get away together, with room to spread out and relax. Located approximately one mile from Downtown Winter Park, and just three miles from Winter Park Resort, you'll enjoy tranquil surroundings with …see more

from $216 / night

$1,512 / week

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from $216 / night

(3) Very Good 

28

Winter Park Vacation home rental

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Relish luxurious living in this one-level loft, located right in the Village at Winter Park, for an experience you won't soon forget. This spacious loft boasts an array of impressive amenities that will surely impress.  Enjoy granite countertops, high-end furnishings an …see more

from $193 / night

$1,351 / week

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from $193 / night

(3) Very Good 

20

Vacation condo with shared pool in Winter Park

Grand County / Winter Park

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • 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 $150 / night

$1,050 / week

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from $150 / night

(2) Very Good 

31

Vacation home in Winter Park

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Wake up and cook yourself breakfast in your fully equipped kitchen, or grab a pastry and cup of coffee at the Starbucks just below. When you're ready to hit the slopes, you are just a few steps away from the chair lifts. After your eventful day, enjoy dinner at one of t …see more

from $118 / night

$826 / week

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from $118 / night

29

Home rental in Winter Park

Grand County / Winter Park

3 15 Min stay varies

  • 3 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
This roomy Winter Park penthouse offers beautiful forested views, easy access to town, and a private hot tub. You'll be in a three-story building on the top floor, close to the bus route. This rental is one mile from the town of Winter Park, three miles from Fraser, an …see more

from $137 / night

$959 / week

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Responds fast!
avg. 2 hours 11 minutes

from $137 / night

(2) Very Good 

28

Vacation home in Winter Park

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
A cozy mountain retreat with a hot tub, a jetted bathtub, and beautiful views of the Continental Divide, this Winter Park vacation rental is three floors of comfort and luxury. This home is located in a quiet neighborhood four miles from Winter Park Resort, and less th …see more

from $110 / night

$770 / week

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Responds fast!
avg. 2 hours 11 minutes

from $110 / night

(1) Very Good 

21

Winter Park Vacation home rental

Grand County / Winter Park

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly
This warm and cozy house will offer you a perfect combination for small or large groups based on this perfect configuration. The family room will offer you the comfort you would expect in a mountain retreat with large vaulted ceilings, beautiful log finishes, a gas fire …see more

from $380 / night

$3,598 - $5,824 / week

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Responds fast!
avg. 1 hour 6 minutes

from $380 / night

(1) Excellent 

33

Vacation home in Winter Park

Grand County / Winter Park

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
  • Pet friendly
Enjoy over 3400 square feet of luxurious living space, right below the slopes at Winter Park Resort! Base Camp 462 has it all: two separate lounges, a gourmet kitchen, private hot tub, heated garage and high-end furnishings and decor throughout. Located in a secluded, …see more

from $358 / night

$2,506 / week

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from $358 / night

(34) Very Good 

29

Vacation home in Winter Park

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
You can't beat the view of the slopes and base village from this one bedroom Zephyr condo. You'll love the special conveniences that come with this unit, such as being able to watch your friends and family ski to the lifts, or cooking up a great apres ski dinner. Add th …see more

from $118 / night

$826 / week

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from $118 / night

(11) Excellent 

24

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 $69 / night

$1,143 / week

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Responds fast!
avg. 1 hour 34 minutes

from $69 / night

(11) Very Good 

30

Vacation log cabin in Winter Park

Grand County / Winter Park

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Ask about children
  • Car not necessary
  • Air conditioning
This cozy yet spacious Log Cabin is located right in the town of Winter Park. It sits on the mountain side, and there is a ski shuttle pickup at the end of the driveway! Bear Claw Cabin is fully furnished, cozy and inviting. The wood logs are all original (cabin was bu …see more

from $209 / night

$1,249 / week

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Responds fast!
avg. 2 hours 15 minutes

from $209 / 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 $200 / night

$1,200 - $1,850 / week

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from $200 / night

(10) Excellent 

33

Vacation home in Winter Park

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Gorgeous wood floors, copper finishings & plush bed linens you can get lost in, are just a few of the touches that will make this decadent loft an absolute oasis of relaxation & comfort during your next fun-filled ski vacation.   Sit back on your spacious deck and watch …see more

from $203 / night

$1,421 / week

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from $203 / night