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

Vacation rentals in Winter Park

Find 5,293 available house rentals from 14 partners
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Top 15 Recommended vacation rentals in Winter Park

Find your perfect vacation rental in Winter Park from just $68 per night!

House Winter Park
-47%
Jan 19 - Jan 26
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with heated pool & jacuzzi

Winter Park, Grand County, Colorado, United States
$395$208
per night
Outstanding(19 ratings)
$395$208
per night
View deal
House Winter Park
-77%
May 3 - May 10
House ∙ 8 guests ∙ 3 bedrooms

House with jacuzzi & terrace

Winter Park, Grand County, Colorado, United States
$434$98
per night
Outstanding(51 ratings)
$434$98
per night
View deal
House Winter Park
-44%
Sep 6 - Sep 13
House ∙ 12 guests ∙ 4 bedrooms

Children-friendly house with jacuzzi, terrace & grill | Dogs allowed

Winter Park, Grand County, Colorado, United States
$598$334
per night
Outstanding(29 ratings)
$598$334
per night
View deal
House Winter Park
Jun 22 - Jun 29
House ∙ 10 guests ∙ 4 bedrooms

House with jacuzzi & barbecue

Winter Park, Grand County, Colorado, United States
$191
per night
Outstanding
$191
per night
View deal
House Winter Park
-75%
Oct 18 - Oct 25
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with hot tub, barbecue & yard

Winter Park, Grand County, Colorado, United States
$1,212$308
per night
Outstanding(88 ratings)
$1,212$308
per night
View deal
House Winter Park
-49%
May 24 - May 31
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly house

Winter Park, Grand County, Colorado, United States
$333$170
per night
Outstanding
$333$170
per night
View deal
Condo Winter Park
-57%
May 3 - May 10
Condo ∙ 6 guests ∙ 5 bedrooms

Family-oriented charming condo with patio

Winter Park, Grand County, Colorado, United States
$191$82
per night
Outstanding(17 ratings)
$191$82
per night
View deal
House Winter Park
-76%
May 10 - May 17
House ∙ 18 guests ∙ 5 bedrooms

Vacation home with barbecue & jacuzzi | Mountain view

Winter Park, Grand County, Colorado, United States
$1,492$351
per night
Excellent(17 ratings)
$1,492$351
per night
View deal
Condo Winter Park
-79%
May 3 - May 10
Condo ∙ 16 guests ∙ 6 bedrooms

Children-friendly wonderful condo with patio, jacuzzi & BBQ | Mountain view

Winter Park, Grand County, Colorado, United States
$1,132$243
per night
Outstanding(51 ratings)
$1,132$243
per night
View deal
Cabin Winter Park
-73%
May 29 - Jun 5
Cabin ∙ 16 guests ∙ 6 bedrooms

Cabin with patio, barbecue & hot tub

Winter Park, Grand County, Colorado, United States
$2,019$540
per night
Excellent(101 ratings)
$2,019$540
per night
View deal
House Winter Park
-70%
May 3 - May 10
House ∙ 16 guests ∙ 5 bedrooms

Child-friendly nice vacation home with sauna, jacuzzi & barbeque | Mountain view | Good for workation

Winter Park, Grand County, Colorado, United States
$699$211
per night
Excellent(27 ratings)
$699$211
per night
View deal
House Winter Park
-81%
May 3 - May 10
House ∙ 9 guests ∙ 4 bedrooms

Family-oriented house with sauna, patio & barbeque | Mountain view | Suitable for remote work | Pets are welcome

Winter Park, Grand County, Colorado, United States
$696$132
per night
Excellent(84 ratings)
$696$132
per night
View deal
House Winter Park
-20%
May 24 - May 31
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with jacuzzi | Mountain view

Winter Park, Grand County, Colorado, United States
$209$167
per night
Outstanding(16 ratings)
$209$167
per night
View deal
Condo Winter Park
May 1 - May 8
Condo ∙ 8 guests ∙ 3 bedrooms

Family-oriented spacious condo with BBQ & terrace | Dogs allowed

Winter Park, Grand County, Colorado, United States
$121
per night
Outstanding(29 ratings)
$121
per night
View deal
Condo Winter Park
-38%
Jun 14 - Jun 21
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped wonderful condo with terrace | Mountain view

Winter Park, Grand County, Colorado, United States
$200$125
per night
Excellent(54 ratings)
$200$125
per night
View deal

Vacation Rentals With Fireplaces

House  Winter Park
Nov 22 - Nov 29
-49%
$587
$300
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly vacation home with heated pool & hot tub | Mountain view

4.8
Outstanding(19 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
House  Winter Park
May 29 - Jun 5
$114
per night
House ∙ 9 guests ∙ 4 bedrooms

Child-friendly vacation home with patio & barbecue | Mountain view | Pet-friendly

4.7
Excellent(29 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
Condo  Winter Park
Jul 1 - Jul 8
$230
per night
Condo ∙ 6 guests ∙ 4 bedrooms

Fully equipped condo | Mountain view

4.6
Excellent(30 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
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Vacation houses with Balconies or Patios

Accommodation  Winter Park
May 3 - May 10
-52%
$2,443
$1,170
per night
Accommodation ∙ 14 guests ∙ 5 bedrooms

Rental with jacuzzi & barbeque | Mountain view

5.0
Outstanding(20 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House  Winter Park
May 3 - May 10
-74%
$439
$113
per night
House ∙ 8 guests ∙ 5 bedrooms

House with terrace & hot tub | Mountain view

4.8
Outstanding(51 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House  Winter Park
May 24 - May 31
-18%
$462
$379
per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with patio, grill & hot tub

4.9
Outstanding(29 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
See all offers

Vacation Rentals With Saunas

Apartment  Winter Park
May 10 - May 17
-83%
$713
$119
per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday apartment with hot tub, sauna & barbecue | Mountain view

5.0
Outstanding(2 ratings)
Winter Park, Grand County, Colorado, United States
Sauna
View deal
House  Winter Park
May 3 - May 10
-74%
$1,183
$313
per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly vacation home with sauna, heated pool & BBQ | Mountain view

5.0
Outstanding(39 ratings)
Winter Park, Grand County, Colorado, United States
Sauna
View deal
House  Winter Park
May 3 - May 10
-74%
$1,183
$313
per night
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with sauna, heated pool & jacuzzi | River view

4.9
Outstanding(70 ratings)
Winter Park, Grand County, Colorado, United States
Sauna
View deal
See all offers

Best Vacation Home Deals in Winter Park

Save up to 76%

House Winter Park
May 24 - May 31
-17%
$363
$300
per night
House ∙ 14 guests ∙ 4 bedrooms

House with patio, BBQ & jacuzzi

4.6
Excellent(42 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Condo Winter Park
May 24 - May 31
-64%
$149
$53
per night
Condo ∙ 4 guests ∙ 1 bedroom

Family-friendly condo

4.7
Excellent(35 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Cabin Winter Park
May 3 - May 10
-76%
$430
$105
per night
Cabin ∙ 10 guests ∙ 3 bedrooms

Cabin with patio & barbecue | Mountain view

4.8
Outstanding(4 ratings)
Winter Park, Grand County, Colorado, United States
View deal

5,293 unique rentals from 14 partner websites can be compared in Winter Park, with prices starting at $68 a night. Every one of the properties from the different providers are directly compared by our algorithm so you can save up to 76%.

Budget-friendly Vacation Rentals in Winter Park

Find Fantastic yet Inexpensive Offers

Condo Winter Park
May 24 - May 31
$127
per night
Condo ∙ 10 guests ∙ 4 bedrooms

Family-oriented condo with terrace | Mountain view

5.0
Outstanding(66 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
May 18 - May 25
$575
per night
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with grill & hot tub | Nature view

5.0
Outstanding(166 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
May 29 - Jun 5
$287
per night
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped vacation home with jacuzzi & barbeque | Mountain view | Dogs allowed

4.6
Excellent(22 ratings)
Winter Park, Grand County, Colorado, United States
View deal

Top-Rated Rentals and Accommodations in Winter Park

Book Vacation Rental Offers with the Highest User Rating

Condo Winter Park
May 29 - Jun 5
$135
per night
Condo ∙ 10 guests ∙ 3 bedrooms

Condo with heated pool, jacuzzi & patio | Mountain view

4.7
Excellent(188 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Condo Winter Park
Oct 18 - Oct 25
-81%
$443
$85
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with hot tub | Mountain view

4.9
Outstanding(168 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Condo Winter Park
May 3 - May 10
$92
per night
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with yard, patio & hot tub | City view

4.7
Excellent(122 ratings)
Winter Park, Grand County, Colorado, United States
View deal

Customer ratings and reviews

How are reviews collected?
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 $306
per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
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 $124
per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.4
Very good(49 ratings)
Winter Park, Grand County, Colorado, United States
View deal

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Popular Rental Amenities in Winter Park

  • Pet-friendly (788)
  • Pool (1,852)
  • Hot tub (2,981)
  • WiFi (5,136)
  • Fireplace (4,545)
  • Kitchen (5,010)
  • Washing machine (3,436)
  • TV (4,784)
  • Balcony/patio (1,455)
  • Parking (1,579)
  • No smoking (4,754)
  • Grill (2,073)

Winter Park is a good vacation spot if you want an accommodation with a pool, as 35% 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 $466 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 $617 (12/27 – 1/3) in Winter Park. Winter Park is most affordable in May (5/10 – 5/17), when average accommodation prices are $479 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 November (11/22 – 11/29). It is easier to find a rental in a week of May (5/3 – 5/10), as only 31% 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 5,293 rentals
💳 Possible discounts up to 76%
🌙 Nightly prices starting at $68
⭐ Popular amenities Pets allowed, Pool and Hot tub
🐾 Pet friendly homes 781 homes
🏊 Vacation rentals with pools 1,838 homes
71,664 reviews
Winter Park vacation rentals have an average rating of 4.6/5 on 71,664 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 $68. Nightly prices for condos are $426 on average. House rentals in Winter Park cost on average $603 per night.

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

There are currently 5,293 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 1,838 vacation rentals available in Winter Park.

Are dogs allowed in vacation rentals in Winter Park?

Sure, there are 781 rentals in Winter Park that allow pets , with an average price of $501 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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