50 Best Winter Park Apartments on Holiday Lettings - Condos

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158 Vacation rentals

(83) 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) 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 tha …see more

from $117 / night

$819 / week

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from $117 / night

(3) Very Good 

17

Winter Park Vacation apartment rental

Grand County / Winter Park

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • 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

$1525 / week

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from $230 / 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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avg. 2 hours 57 minutes

from $100 / 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 $140 / night

$980 / week

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from $140 / 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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Responds fast!
avg. 1 hour 10 minutes

from $149 / night

(4) Very Good 

Certificate of Excellence

8

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 $79 / night

$594 - $1300 / week

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Responds fast!
avg. 3 hours 14 minutes

from $79 / night

(9) 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 $129 / night

$1943 / week

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Responds fast!
avg. 3 hours 44 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 $299 / night

$2093 - $7350 / week

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from $299 / night

(10) 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

$1943 / week

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Responds fast!
avg. 3 hours 44 minutes

from $129 / 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

$1000 - $3500 / week

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Responds fast!
avg. 1 hour 57 minutes

from $150 / night

(2) 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 $99 / night

$1143 / week

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Responds fast!
avg. 3 hours 44 minutes

from $99 / night

(6) Excellent 

24

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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Responds fast!
avg. 3 hours 44 minutes

from $119 / 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 $99 / night

$1143 / week

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Responds fast!
avg. 3 hours 44 minutes

from $99 / night

(5) 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 $99 / night

$1143 / week

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Responds fast!
avg. 3 hours 44 minutes

from $99 / night

(4) Excellent 

22

Vacation condo with shared pool in Winter Park

Grand County / Winter Park

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • 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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Responds fast!
avg. 3 hours 44 minutes

from $99 / night

36

Home rental in Winter Park

Grand County / Winter Park

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
This charming Winter Park vacation rental offers guests close proximity to local activities, shared hot tub access, and attractions as well as stunning views of the Continental Divide. Located 39 miles from summer access to Rocky Mountain National Park, and only three m …see more

from $99 / night

$693 / week

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from $99 / 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

(36) Excellent 

25

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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Responds fast!
avg. 3 hours 44 minutes

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

(34) Very Good 

33

Winter Park Vacation home rental

Grand County / Winter Park

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Imagine sharing a family breakfast in front of the kitchen fireplace while the snow falls outside. With high end finishes like hardwood and granite throughout the home, this and enchanting place for warm family memories. Another fireplace and flat screen in the living a …see more

from $273 / night

$1911 / week

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from $273 / 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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Responds fast!
avg. 1 hour 1 minutes

from $140 / night

(1) Excellent 

33

Winter Park Vacation home rental

Grand County / Winter Park

3 11 Min stay varies

  • 3 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
You will love the privacy and convenience of this great location.  This bright and roomy townhome is located in a small complex above Downtown Winter Park with a tranquil pond and beautiful aspen trees.  The main level living area welcomes you in with freshly updated dé …see more

from $189 / night

$1323 / week

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from $189 / 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

(12) Very Good 

24

Home rental in Winter Park

Grand County / Winter Park

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Located smack-dab in the middle of town, this new townhome is the perfect spot to enjoy your Winter Park vacation. The home has three private decks, on which you can grill, relax in the hot tub, or enjoy the views of the Continental Divide.  Don't miss miss out on this …see more

from $189 / night

$1323 / week

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from $189 / 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

(16) Very Good 

29

Vacation home in Winter Park

Grand County / Winter Park

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
This is one of those vacation destinations that will keep you coming back. With incredible views from your private balcony, to an expansive open layout and enough seating for large families to spread out, this is a comfortable and thoughtfully-decorated mountain getaway …see more

from $213 / night

$1491 / week

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from $213 / night

24

Vacation home rental

Grand County / Winter Park

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Centrally located in downtown Winter Park, this ground-floor condo is a great romantic getaway for an active couple or a cozy space to share with family. Walk to restaurants like Hernando's Pizza and Pasta Pub, the cinema/bowling alley complex, the rec center with a wat …see more

from $85 / night

$595 / week

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from $85 / night

(6) 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

$1943 / week

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Responds fast!
avg. 3 hours 44 minutes

from $129 / night

(7) 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 $99 / night

$1143 / week

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Responds fast!
avg. 3 hours 44 minutes

from $99 / night

(1) Excellent 

31

Home rental in Winter Park with shared pool

Grand County / Winter Park

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
This fully-remodeled condo has it all with a prime year round location and a modern mountain feel that you won't want to leave.  Enjoy the bright and open living space with updated kitchen and large picture windows and private deck with views. Warm up in the private sau …see more

from $159 / night

$1113 / week

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from $159 / night

(5) Very Good 

31

Winter Park Vacation home rental

Grand County / Winter Park

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Enjoy the peaceful atmosphere of Sawmill Station, whilst being only a short stroll from all the conveniences of town, in this gorgeous three-story townhome. This end-unit is in excellent condition with new furnishings and authentic Colorado art & décor, and offers plent …see more

from $273 / night

$1911 / week

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from $273 / 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 $99 / night

$1143 / week

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Responds fast!
avg. 3 hours 44 minutes

from $99 / night

(4) 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

$1943 / week

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Responds fast!
avg. 3 hours 44 minutes

from $129 / night

28

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 $193 / night

$1351 / week

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from $193 / 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

$3207 / week

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from $459 / night

28

Vacation log cabin in Winter Park

Grand County / Winter Park

2 10 Min stay varies

  • 2 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
*Please note that if you check-in/out on a major holiday - the reservation may be subject to a double cleaning fee.  For your next alpine retreat, come escape to this spacious Winter Park vacation rental cabin, nestled in a serene wooded setting overlooking a beautiful …see more

from $169 / night

$1183 - $2275 / week

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from $169 / night

(10) Excellent 

26

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 $204 / night

$1422 / week

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from $204 / 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

(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