50 Best Winter Park Apartments on Holiday Lettings - Condos

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734 Vacation rentals

(4) Very Good 

14

Vacation villa with shared pool in Winter Park

Grand County / Winter Park

4 Min stay varies

  • Sleeps 4
  • Min stay varies
  • 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 - $700 / week

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avg. 2 hours 6 minutes

from $50 / night

(1) Excellent 

24

Ski home to rent in Winter Park

Grand County / Winter Park

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ski
  • 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 $192 / night

$1,344 / week

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avg. 29 minutes

from $192 / night

(1) Excellent 

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 $130 / night

$910 / week

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from $130 / night

24

Winter Park ski apartment to rent.

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Escape to a Rocky Mountain paradise when you book this 1-bedroom, 1-bath vacation rental condo in Winter Park, which sleeps 4. Boasting all the comforts of home, access to community amenities and an unbeatable location only minutes from the slopes, this unit is ideal fo …see more

from $95 / night

$665 / week

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avg. 29 minutes

from $95 / night

24

Ski apartment to rent in Winter Park

Grand County / Winter Park

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
Escape to beautiful Winter Park in comfort and style when you stay at this 2-bedroom, 2-bathroom vacation rental condo that sleeps up to 7 lucky travelers. You'll be within a 5-minute walk of the complimentary ski shuttle to Winter Park Ski Resort and close to a variety …see more

from $115 / night

$805 / week

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avg. 29 minutes

from $115 / night

(3) Excellent 

43

Winter Park ski apartment to rent.

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • 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

$995 - $3,550 / week

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avg. 1 hour 44 minutes

from $150 / night

(1) Excellent 

26

Ski home to rent in Winter Park

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ski
  • 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 $290 / night

$2,030 / week

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avg. 29 minutes

from $290 / night

(2) Excellent 

23

Winter Park ski condo to rent.

Grand County / Winter Park

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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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avg. 1 hour 59 minutes

from $149 / night

26

Winter Park ski apartment to rent.

Grand County / Winter Park

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Begin your alpine retreat at this 2-bedroom, 2-bath vacation rental condo in Winter Park! Offering an ideal location - just minutes from Winter Park Resort, 1 block from downtown, and steps from community amenities - this charming condo invites you to shop, dine, relax, …see more

from $100 / night

$700 / week

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avg. 29 minutes

from $100 / night

(11) 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 2 bedroo …see more

from $129 / night

$1,943 / week

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from $129 / night

(4) Excellent 

17

Ski apartment to rent in Winter Park

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ski
  • 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 $120 / night

$660 - $1,380 / week

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avg. 1 hour 27 minutes

from $120 / night

24

Winter Park ski home to rent.

Grand County / Winter Park

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ski
  • Child friendly
Skiers and hikers pack your bags, as this 3-bedroom, 3-bathroom Winter Park vacation rental townhome is a true outdoorsman’s paradise! With remarkable hiking trails nearby and world class ski slopes only a short drive away, the alpine excursions are endless. Up to 10 gu …see more

from $155 / night

$1,085 / week

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avg. 29 minutes

from $155 / night

33

Ski apartment to rent in Winter Park

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Have the ultimate Rocky Mountain getaway by staying at this charming 1-bedroom, 1-bathroom Winter Park vacation rental condo which is best suited for 2 people, but can accommodate up to 4. Ideally situated within proximity of Winter Park Ski Resort, Rocky Mountain Natio …see more

from $99 / night

$693 / week

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avg. 29 minutes

from $99 / night

(3) Very Good 

16

Winter Park Vacation apartment rental

Grand County / Winter Park

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
We understand that you go to the mountains to feel like you're truly in the mountains - the fresh smell of pine trees from your own private balcony, the exhilarating trails a couple blocks away in Arapahoe National Forest and the convenient free ski shuttle that stops a …see more

from $230 / night

$1,525 / week

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from $230 / night

(3) Very Good 

30

Winter Park Vacation home rental

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
*SUMMER 2018 PLAZA CONSTRUCTION- This will NOT impact ski season bookings: Please note that the plaza between Zephyr Mountain Lodge and the Private Lesson Center is being renovated this summer. Work will begin on April 23rd and demolition will be completed by June 1st w …see more

from $193 / night

$1,351 / week

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from $193 / night

(12) Excellent 

24

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 2 bedroo …see more

from $129 / night

$1,943 / week

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from $129 / night

(9) Very Good 

7

Vacation log cabin in Winter Park

Grand County / Winter Park

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
We only need three words to describe our small, but perfect retreat… 1. LOCATION! 2. LOCATION! 3. LOCATION! You’ve just found the perfect place to escape to in Winter Park. Aside from the beauty of the mountains and the unbelievable skiing, the town of Winte …see more

from $110 / night

$650 / week

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from $110 / 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

(1) Excellent 

27

Vacation home in Winter Park

Grand County / Winter Park

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Pet friendly
This beautiful mountain home is centrally located in the Fraser Valley. It is luxury in a rustic mountain setting. The home is situated on a large wooded lot giving you the peace and tranquility you are looking for in a mountain getaway. Yet, the home is just minutes aw …see more

from $390 / night

$2,730 / week

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avg. 1 hour 15 minutes

from $390 / night

29

Ski home to rent in Winter Park

Grand County / Winter Park

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Experience the majesty of the Rocky Mountains from the luxury of this 5-bedroom, 4.5-bathroom vacation rental home for up to 12 in Winter Park. After a day on the slopes, there's no better way to unwind than with a soak in the hot tub, steam in the sauna, or family movi …see more

from $400 / night

$2,800 - $7,000 / week

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avg. 29 minutes

from $400 / night

(1) Excellent 

26

Ski villa to rent in Winter Park

Grand County / Winter Park

9 36 3 nights min

  • 9 bedrooms
  • Sleeps 36
  • 3 nights min
  • Ski
  • Child friendly
  • Air conditioning
Emberwood Lodge is an ultra luxe 7,000 square foot cabin offering accommodations to those that expect the absolute finest in amenities. Emberwood is among the largest private rentals in Winter Park, offering comfortable capacity for up to 36 guests in beds. Luxuriously …see more

from $3,000 / night

$21,000 / week

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avg. 2 hours 51 minutes

from $3,000 / night

24

Winter Park ski townhouse to rent.

Grand County / Winter Park

3 8 Min stay varies

  • 3 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

$903 / week

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from $129 / night

(6) Excellent 

19

Ski home to rent in Winter Park

Grand County / Winter Park

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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

$1,200 - $3,200 / week

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from $195 / 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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avg. 1 hour 15 minutes

from $380 / 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 $110 / night

$770 / week

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avg. 2 hours 51 minutes

from $110 / 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 2 bedroo …see more

from $129 / night

$1,943 / week

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from $129 / night

(4) 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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from $129 / night

43

Vacation home in Winter Park

Grand County / Winter Park

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
Looking for the perfect mix of family entertainment, sublime comfort, and superb amenities? The Lupine Lodge is the answer. This five bedroom lodge is spread over two levels with giant log beam supports that blend amenities, entertainment, and comfort to perfection. …see more

from $567 / night

$3,969 / week

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from $567 / night

(2) Excellent 

18

Vacation condo rental

Grand County / Winter Park

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
Hideaway is an updated, quiet 2 bedroom, 2 bathroom condo in an ideal location. Relax in front of the natural gas fire and create memories around a beautiful log table. The living area has lots of natural light and the tall pines help create that cozy mountain feel. …see more

from $140 / night

$900 / week

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avg. 49 minutes

from $140 / night

15

Winter Park Vacation apartment rental

Grand County / Winter Park

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Experience the ultimate Rocky Mountain getaway by staying at this charming 1 bedroom, 1 bath Winter Park condo which sleeps 4. Ideally situated within close proximity to Winter Park Ski Resort, downtown Winter Park, Rocky Mountain National Park, restaurants, and more, t …see more

from $129 / night

$903 / week

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from $129 / night

(7) Excellent 

24

Ski home to rent in Winter Park

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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from $129 / night

(11) Very Good 

30

Vacation home in Winter Park

Grand County / Winter Park

4 14 Min stay varies

  • 4 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
This elegant mountain escape brings luxury, comfort and convenience to the slopes at Winter Park Resort. High-end mountain decor and all the sought after amenities will captivate and entertain at every turn. Featured highlights include a private hot tub, TWO lounges, …see more

from $358 / night

$2,506 / week

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from $358 / night

36

Vacation home in Winter Park

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Professional decor with a deliberate fashion-forward modern new age feel will almost distract you from the majestic resort and mountain views in this awesome new Lakota Trailside townhome with private hot tub. Hardwood floors lead you into this chic townhome where you …see more

from $313 / night

$2,191 / week

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from $313 / night

(5) Very Good 

33

Vacation home in Winter Park

Grand County / Winter Park

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
*SUMMER 2018 PLAZA CONSTRUCTION- This will NOT impact ski season bookings: Please note that the plaza between Zephyr Mountain Lodge and the Private Lesson Center is being renovated this summer. Work will begin on April 23rd and demolition will be completed by June 1st w …see more

from $167 / night

$1,169 / week

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from $167 / night

35

Vacation condo in Winter Park

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
Our Lakota Antlers townhome is designed for family fun. Enjoy one of the five flatscreen TVs, theater room, and air hockey table that converts into a ping-pong table. The center level of this tri-level townhome has an open floor plan centered around a 55" flatscreen s …see more

from $351 / night

$2,457 / week

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from $351 / night

(11) 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 2 bedroo …see more

from $129 / night

$1,943 / week

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from $129 / night

(15) Very Good 

31

Vacation home in Winter Park

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
*SUMMER 2018 PLAZA CONSTRUCTION- This will NOT impact ski season bookings: Please note that the plaza between Zephyr Mountain Lodge and the Private Lesson Center is being renovated this summer. Work will begin on April 23rd and demolition will be completed by June 1st w …see more

from $167 / night

$1,169 / week

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from $167 / night

(10) Excellent 

35

Vacation home in Winter Park

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
*SUMMER 2018 PLAZA CONSTRUCTION- This will NOT impact ski season bookings: Please note that the plaza between Zephyr Mountain Lodge and the Private Lesson Center is being renovated this summer. Work will begin on April 23rd and demolition will be completed by June 1st w …see more

from $203 / night

$1,421 / week

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from $203 / night

(8) 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 1 bedroo …see more

from $79 / night

$1,333 / week

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from $79 / night

(2) Excellent 

29

Winter Park ski home to rent.

Grand County / Winter Park

9 28 3 nights min

  • 9 bedrooms
  • Sleeps 28
  • 3 nights min
  • Ski
  • Child friendly
  • Car not necessary
Property, called Winter Park Chateau, was built as a Victorian Style boutique Inn and now being selectively rented as a full house rental. The 9,000 square foot property features a gourmet Kitchen and large entertainment area, landscaped back yard with a gazebo and din …see more

from $1,000 / night

$7,000 / week

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from $1,000 / night