Vacation rentals in Winter Park - HomeToGo base64Hash Vacation rentals in Winter Park - HomeToGo

Vacation rentals in Winter Park

Find 5,199 available house rentals from 14 partners
Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • Cabin
    • House

  • Distance to center

    • 1 km
    • 2 km
    • 5 km

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Hot tub
    • WiFi
    • Fireplace
    • Kitchen
    • Washing machine
    • TV
    • Balcony/patio
    • Parking
    • Microwave
    • Dishwasher
    • Air conditioning
    • Sauna
    • Yard
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Winter Park

Find your perfect vacation rental in Winter Park from just $128 per night!

House Winter Park
-55%
May 31 - Jun 7
House ∙ 14 guests ∙ 3 bedrooms

Children-Friendly House with Patio & Barbecue | Next to the Ski

Winter Park, Grand County, Colorado, United States
$1,177$499
per night
Outstanding(104 ratings)
$1,177$499
per night
View deal
House Winter Park
Jun 21 - Jun 28
House ∙ 10 guests ∙ 5 bedrooms

House with Terrace & Grill | Mountain View

Winter Park, Grand County, Colorado, United States
$482
per night
Outstanding(54 ratings)
$482
per night
View deal
House Winter Park
Jun 14 - Jun 21
House ∙ 12 guests ∙ 4 bedrooms

Children-Friendly House with Sauna, Terrace & Grill | Mountain View

Winter Park, Grand County, Colorado, United States
$462
per night
Outstanding(112 ratings)
$462
per night
View deal
Condo Winter Park
-24%
Jun 2 - Jun 9
Condo ∙ 4 guests ∙ 1 bedroom

Family-Friendly Beautiful Condo with Terrace & Pool

Winter Park, Grand County, Colorado, United States
$287$119
per night
Outstanding(45 ratings)
$287$119
per night
View deal
Studio flat Winter Park
Jun 14 - Jun 21
Studio flat ∙ 4 guests ∙ 1 bedroom

Family-Friendly Charming Studio with Jacuzzi | Close to the Ski

Winter Park, Grand County, Colorado, United States
$139
per night
Excellent(33 ratings)
$139
per night
View deal
House Winter Park
-51%
Apr 26 - May 3
House ∙ 9 guests ∙ 3 bedrooms

Children-Friendly Wonderful Vacation Home with Terrace & Barbeque | Pet-Friendly

Winter Park, Grand County, Colorado, United States
$665$223
per night
Excellent(30 ratings)
$665$223
per night
View deal
House Winter Park
-76%
Apr 28 - May 5
Free cancellation
House ∙ 14 guests ∙ 6 bedrooms

Vacation Home with Heated Pool, Grill & Sauna | Lake View

Winter Park, Grand County, Colorado, United States
$3,131$749
per night
Outstanding(77 ratings)
$3,131$749
per night
View deal
Apartment Winter Park
-91%
May 3 - May 10
Free cancellation
Apartment ∙ 4 guests ∙ 1 bedroom

Holiday Apartment with Pool & Hot Tub

Winter Park, Grand County, Colorado, United States
$1,028$128
per night
Excellent(80 ratings)
$1,028$128
per night
View deal
Condo Winter Park
-56%
May 16 - May 23
Condo ∙ 10 guests ∙ 3 bedrooms

Condo with Barbeque & Patio

Winter Park, Grand County, Colorado, United States
$665$258
per night
Outstanding(66 ratings)
$665$258
per night
View deal
House Winter Park
-41%
Sep 15 - Sep 22
House ∙ 12 guests ∙ 4 bedrooms

Children-Friendly Vacation Home with Barbecue, Terrace & Hot Tub | Pets Allowed

Winter Park, Grand County, Colorado, United States
$655$445
per night
Outstanding(29 ratings)
$655$445
per night
View deal
House Winter Park
-84%
Jul 26 - Aug 2
House ∙ 8 guests ∙ 5 bedrooms

Family-Oriented Ample House with Patio, BBQ & Hot Tub | Next to the Ski | Suitable for Remote Work

Winter Park, Grand County, Colorado, United States
$1,986$531
per night
Outstanding(51 ratings)
$1,986$531
per night
View deal
Condo Winter Park
-49%
Apr 5 - Apr 12
Condo ∙ 8 guests ∙ 3 bedrooms

Children-Friendly Condo with Heated Pool, Hot Tub & Terrace

Winter Park, Grand County, Colorado, United States
$751$218
per night
Outstanding(59 ratings)
$751$218
per night
View deal
House Winter Park
-51%
Mar 15 - Mar 22
House ∙ 12 guests ∙ 3 bedrooms

Child-Friendly Vacation Home with Grill & Patio | Mountain View

Winter Park, Grand County, Colorado, United States
$1,384$343
per night
Outstanding(108 ratings)
$1,384$343
per night
View deal
Condo Winter Park
-43%
May 3 - May 10
Condo ∙ 8 guests ∙ 2 bedrooms

Family-Friendly Condo with Jacuzzi, Heated Pool & Terrace | Pets Allowed

Winter Park, Grand County, Colorado, United States
$573$212
per night
Outstanding(68 ratings)
$573$212
per night
View deal
House Winter Park
-75%
Apr 22 - Apr 29
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home with Terrace & Jacuzzi | Mountain View

Winter Park, Grand County, Colorado, United States
$914$397
per night
Excellent(48 ratings)
$914$397
per night
View deal

Vacation rentals and apartments with air conditioning

Apartment Winter Park
Nov 1 - Nov 8
-53%
$953
$167
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment with Hot Tub

5.0
Outstanding(4 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Air conditioning
View deal
House Winter Park
May 3 - May 10
-52%
$864
$232
per night
House ∙ 4 guests ∙ 2 bedrooms

Children-Friendly House with Heated Pool, Patio & Barbecue | Mountain View

5.0
Outstanding(2 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Air conditioning
View deal
Maisonette Winter Park
Apr 12 - Apr 19
-72%
$1,751
$407
per night
Maisonette ∙ 12 guests ∙ 4 bedrooms

Fully Equipped Duplex with Heated Pool, Sauna & Grill | Good for Workation

Winter Park, Grand County, Colorado, United States
Air conditioning
View deal
See all offers

Best Vacation Home Deals in Winter Park

Save up to 85%

Apartment Winter Park
Nov 8 - Nov 15
-85%
$1,053
$195
per night
Apartment ∙ 7 guests ∙ 3 bedrooms

Rental Apartment with Barbecue & Patio | Mountain View | Suitable for Remote Work

4.8
Outstanding(33 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
House Winter Park
May 3 - May 10
-46%
$3,150
$735
per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation Home with BBQ, Jacuzzi & Terrace | Mountain View

5.0
Outstanding(71 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
Apartment Winter Park
Nov 2 - Nov 9
-85%
$1,181
$207
per night
Apartment ∙ 9 guests ∙ 4 bedrooms

Apartment with Barbeque | Mountain View

Winter Park, Grand County, Colorado, United States
Free cancellation
View deal

5,199 unique rentals from 14 partner websites can be compared in Winter Park, with prices starting at $128 a night. Every one of the properties from the different providers are directly compared by our algorithm so you can save up to 85%.

Budget-friendly Vacation Rentals in Winter Park

Find Fantastic yet Inexpensive Offers

House Winter Park
Jun 21 - Jun 28
-16%
$410
$185
per night
House ∙ 11 guests ∙ 2 bedrooms

Family-Oriented House | Pet-Friendly

3.7
Good(12 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Apartment Winter Park
Nov 8 - Nov 15
-85%
$1,512
$276
per night
Apartment ∙ 12 guests ∙ 3 bedrooms

Family-Oriented Holiday Apartment with BBQ & Terrace | Mountain View

5.0
Outstanding(108 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
Apartment Winter Park
Nov 8 - Nov 15
-85%
$689
$132
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment with Sauna

5.0
Outstanding(3 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal

Top-Rated Rentals and Accommodations in Winter Park

Book Vacation Rental Offers with the Highest User Rating

Condo Winter Park
Jun 6 - Jun 13
-39%
$1,633
$385
per night
Condo ∙ 10 guests ∙ 4 bedrooms

Condo with terrace, BBQ & pool | Mountain view

5.0
Outstanding(103 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Apartment Winter Park
Apr 19 - Apr 26
-87%
$2,505
$390
per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Family-oriented holiday apartment with barbecue, terrace & jacuzzi | Ski nearby | Suitable for remote work

4.9
Outstanding(51 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
House Winter Park
Apr 19 - Apr 26
-54%
$903
$264
per night
House ∙ 8 guests ∙ 3 bedrooms

House with jacuzzi & terrace

4.7
Excellent(48 ratings)
Winter Park, Grand County, Colorado, United States
View deal

Customer ratings and reviews

How are reviews collected?
Randall V.
Guest verified by HomeToGo

Enjoyed the stay. Will rebook when we return. Just a few suggestions. Need more coasters. Need a regular kitchen broom. Refrigerator was too cold and froze a lot of our food. Had to turn it down. Need hand soap and air freshener for bathrooms. One of the knobs on the grill wouldn’t turn off and we smelled gas. Turned off at the tank. Tried to take trash to the designated location on Reunion but couldn’t find receptacle possibly because snow had built up. Need better info on kitchen items provided (crock pot waffle maker).

Reviewed on 12/30/2024 | Family
House Winter Park
from $500
per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(9 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $500
per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(9 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal
Jane K.
Guest verified by HomeToGo

Absolutely wonderful. New, convenient, and beautifully appointed with new, clean appliances, and plenty of sunshine. Hot tub and fire pit make for a nice social gathering spot. Very quiet. Loved the Nordic ski and hiking available right outside our door!

Reviewed on 3/7/2024 | Group
House Winter Park
from $336
per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $336
per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal
Izabela P.
Guest verified by HomeToGo

Difficulties with parking (QR code did not work, after 4 days our bill was close to 400,00 instead 76 dollars). No towels for hot tub. In the shower, no shower gel.

Reviewed on 1/31/2024 | Couple
Condo Winter Park
from $142
per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.4
Very good(50 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $142
per night
Condo ∙ 4 guests ∙ 1 bedroom
4.4
Very good(50 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal

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Popular Rental Amenities in Winter Park

  • Pet-friendly (808)
  • Pool (1,921)
  • Hot tub (3,353)
  • WiFi (4,946)
  • Fireplace (4,374)
  • Kitchen (4,847)
  • Washing machine (2,870)
  • TV (4,658)
  • Balcony/patio (1,471)
  • Parking (1,352)
  • No smoking (4,596)
  • Grill (2,089)

Winter Park is a good vacation spot if you want an accommodation with a pool, as 37% of the properties have one. Condo with pools in Winter Park are a wonderful choice for groups of 6 and have an average cost of $486 per night. nearly half of Winter Park's rentals with pools are located within two miles of water, spend your days lounging by the pool or the waterfront.

Price and Availability Index in Winter Park

Click on any bar to see price and availability information

Vacation Rental Price Information in Winter Park

The price graph will give you the average nightly price for the upcoming months of the year in Winter Park. The average nightly rate for vacation homes can go up to $1,216 (12/20 – 12/27) in Winter Park. Winter Park is most affordable in April (4/5 – 4/12), when average accommodation prices are $350 a night.

Rental availability information in Winter Park

The availability graph shows the most competitive months to book a vacation rental in Winter Park. The week with the lowest percentage of available accommodations is in January (1/17 – 1/24). It is easier to find a rental in a week of May (5/17 – 5/24), as only 41% of the accommodations are booked.

Ski the slopes and savor superb views with Winter Park vacation homes

Spacious cabin rentals and modern condo vacation rentals in Winter Park put you near all the action on the ski resort's mountainside. Enjoy the woodsy locale and proximity to Colorado's scenic nature.

What are the best activities for families in Winter Park?

Young mountaineers

Beyond ski school, children can enjoy tubing, ice skating, and snowshoeing. In summer, Winter Park, despite a name reminiscent of endless snow, is just as exciting. The resort's alpine slide is the longest of its kind in mountainous Colorado. Kids can fly down the hill in joy on the safe yet thrilling track.

Treat kids to a day out fishing at one of the area's child-friendly ponds. The stocked North Pond at Lion's Fishing Ponds is suitable for ages 14 and younger, while the stocked pond at Kaibab Park is for those 15 and under. Casting a line should get some bites!

Where are the unique attractions in Winter Park?

Adrenaline rushes

Winter Park Ski Resort is one of the top, best-known ski resorts in Colorado, not to mention the longest-running, at 75 years old. Explore seven territories of highly varied terrain, from challenging moguls in Mary Jane Territory to backcountry-like Vasquez Ridge.

Colorado has a collection of 53 extra-tall mountains over 14,000 feet, referred to locally as "14-ers." Winter Park is home to a few of these mammoths, with the closest and least difficult pair being Mount Bierstadt and Mount Evans.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 5,199 rentals
💳 Possible discounts up to 85%
🌙 Nightly prices starting at $128
⭐ Popular amenities Pets allowed, Pool and Hot tub
🐾 Pet friendly homes 806 homes
🏊 Vacation rentals with pools 1,923 homes
67,092 reviews
Winter Park vacation rentals have an average rating of 4.6/5 on 67,092 reviews left by travelers.

Frequently Asked Questions

What is the price per night for a vacation rental in Winter Park?

The nightly price of accommodations in Winter Park starts at $128. Nightly prices for condos are $398 on average. House rentals in Winter Park cost on average $642 per night.

How many vacation rentals are available for booking in Winter Park?

There are currently 5,199 vacation homes in Winter Park to browse and book for your trip.

What amenities are most popular for vacation homes in Winter Park?

If you're looking to book a vacation rental in Winter Park, others search for accommodation with Pets allowed, Pool and Hot tub.

How many vacation homes with a pool are in Winter Park?

Check out 1,923 vacation rentals available in Winter Park.

Are dogs allowed in vacation rentals in Winter Park?

Sure, there are 806 rentals in Winter Park that allow pets , with an average price of $522 per night.

What's the best time to travel to Winter Park?

If you are looking for a vacation home in Winter Park, keep in mind that rainy season is usually in May or February, with March often being the driest.

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