50 Best Winter Park Apartments on Holiday Lettings - Condos

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448 Vacation rentals

(1) Excellent 

18

Vacation condo with shared pool in Winter Park

Grand County / Winter Park

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • 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

33

Winter Park Vacation apartment rental

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
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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avg. 52 minutes

from $99 / night

24

Vacation apartment with shared pool in Winter Park

Grand County / Winter Park

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Escape to a Rocky Mountain paradise when you book this 1-bedroom, 1-bath vacation rental condo in Winter Park, which sleeps 3. 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 - $1,715 / week

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avg. 52 minutes

from $95 / night

(97) 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 - $825 / week

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from $99 / 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 $192 / night

$1,344 - $3,668 / week

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avg. 52 minutes

from $192 / 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 / week

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avg. 3 hours 8 minutes

from $50 / 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 $149 / night

$1,943 / week

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Responds fast!
avg. 3 hours 37 minutes

from $149 / 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 luxury 2 …see more

from $149 / night

$1,943 / week

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Responds fast!
avg. 3 hours 37 minutes

from $149 / 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 $290 / night

$2,030 - $7,665 / week

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avg. 52 minutes

from $290 / 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 18 minutes

from $380 / 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 18 minutes

from $390 / 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 $149 / night

$1,143 / week

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Responds fast!
avg. 3 hours 37 minutes

from $149 / night

(5) Very Good 

32

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

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 $149 / night

$1,043 / week

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Responds fast!
avg. 3 hours 37 minutes

from $149 / night

27

Vacation home in Winter Park

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Enjoy the ski area views from your living room, deck or hot tub in this three bedroom, three level Lakota Antlers Townhome. Warm radiant heated floors and a sprawling sectional great you as you enter the townhome. Sink in and stay warm by the fire while catching a mov …see more

from $261 / night

$1,827 / week

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from $261 / 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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Responds fast!
avg. 1 hour 54 minutes

from $149 / 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

27

Vacation home in Winter Park

Grand County / Winter Park

3 11 Min stay varies

  • 3 bedrooms
  • Sleeps 11
  • 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

(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. 2 hours 18 minutes

from $150 / 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
The best features of Vasquez Retreat are the beautiful sauna, the fire ring with stone seating in the yard, and the spacious floor plan with lots of large windows, high ceilings and plenty of bedding for larger groups. Sleeping Arrangements: First bedroom with Queen …see more

from $419 / night

$2,933 / week

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from $419 / night

(27) Very Good 

34

Home rental 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

(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 $149 / night

$1,943 / week

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Responds fast!
avg. 3 hours 37 minutes

from $149 / 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 $99 / night

$693 / week

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Responds fast!
avg. 22 minutes

from $99 / night

31

Vacation home in Winter Park

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
This development is just above downtown Winter Park and rarely has rentals - it's just one building with a private underground heated garage, elevator to your front door, and nice seculded feeling. Easy to walk to town in summertime. On the free shuttle route. And the …see more

from $195 / night

$1,365 / week

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from $195 / 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 $89 / night

$1,783 / week

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Responds fast!
avg. 3 hours 37 minutes

from $89 / 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. 3 hours 37 minutes

from $69 / 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

(4) Excellent 

27

Vacation home in Winter Park

Grand County / Winter Park

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
Put on the fire and relax while you enjoy a good book or put on a movie. You will love the bubbly private hot tub and soaking in the beautiful views of the mountains and the ski slopes. Families with small children love to find this home fully equipped with a pack 'n' p …see more

from $200 / night

$1,400 / week

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from $200 / 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

(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 $149 / night

$1,943 / week

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Responds fast!
avg. 3 hours 37 minutes

from $149 / 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 $516 / night

$3,612 / week

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from $516 / night

26

Home rental in Winter Park

Grand County / Winter Park

6 20 Min stay varies

  • 6 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
  • Pet friendly
Relaxation at its best in the Colorado Mountains, with a home that has 6 bedrooms separated into four distinct and private areas. It also has three separate living areas. Enjoy the company of others, but you can always retreat to your own space. We love this house when …see more

from $575 / night

$4,025 / week

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Responds fast!
avg. 1 hour 18 minutes

from $575 / 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

25

Winter Park Vacation home rental

Grand County / Winter Park

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
A great spot for families and groups who want comfort and convenience!  Trailhead Lodges is one of the newest neighborhoods in the heart of Downtown Winter Park with higher end amenities and easy access to everything you need for your Rocky Mountain getaway.  This condo …see more

from $175 / night

$1,225 / week

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from $175 / night

(3) Very Good 

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. 3 hours 37 minutes

from $69 / 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

Inquire View

from $167 / night

(5) Very Good 

26

Winter Park Vacation home rental

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
This end-unit townhome is just a short stroll from the restaurants and shops in town. Enjoy new furnishings, authentic Colorado art & décor, private deck, and much more! Sawmill Station 220 offers plenty of room for families & friends to spread out & relax in after a fu …see more

from $300 / night

$2,100 / week

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from $300 / night

24

Home rental in Winter Park

Grand County / Winter Park

6 24 Min stay varies

  • 6 bedrooms
  • Sleeps 24
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
Perfect setting in the Colorado Mountains, with a home that has 8 sleeping areas (5 dedicated bedrooms, private game room has futon and queen air mattress available, living room and family room both have a sleeper sofa). The game room also includes a ping pong table! …see more

from $445 / night

$2,590 - $2,877 / week

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Responds fast!
avg. 1 hour 18 minutes

from $445 / 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 luxury 2 …see more

from $149 / night

$1,943 / week

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Responds fast!
avg. 3 hours 37 minutes

from $149 / 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
Families and friends welcome! This home is steeped in the essence of home with all the spoils of delight. Nestled in the nature, only a third of a mile from the resort and two miles from town, this neighborhood townhouse provides quiet ambiance and convenient amenities …see more

from $353 / night

$2,471 / week

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from $353 / night