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

Vacation rentals in Winter Park

Find 5,179 available house rentals from 12 partners
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1 guest
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Top 15 Recommended vacation rentals in Winter Park

Find your perfect vacation rental in Winter Park from just $127 per night!

House Winter Park
-77%
May 24 - May 31
House ∙ 12 guests ∙ 5 bedrooms

House with jacuzzi, BBQ & patio | Mountain view

Winter Park, Grand County, Colorado, United States
$2,145$749
per night
Outstanding(33 ratings)
$2,145$749
per night
View deal
House Winter Park
Jul 11 - Jul 18
House ∙ 12 guests ∙ 4 bedrooms

Child-friendly vacation home with sauna, barbeque & terrace | Mountain view

Winter Park, Grand County, Colorado, United States
$461
per night
Outstanding(112 ratings)
$461
per night
View deal
House Winter Park
Apr 4 - Apr 11
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with yard, BBQ & terrace | Mountain view

Winter Park, Grand County, Colorado, United States
$604
per night
Outstanding(245 ratings)
$604
per night
View deal
House Winter Park
-75%
Aug 4 - Aug 11
House ∙ 14 guests ∙ 6 bedrooms

House with hot tub, barbeque & patio | Mountain view | Perfect for remote work

Winter Park, Grand County, Colorado, United States
$1,520$574
per night
Outstanding(100 ratings)
$1,520$574
per night
View deal
House Winter Park
-20%
Aug 2 - Aug 9
House ∙ 7 guests ∙ 2 bedrooms

House with grill, jacuzzi & terrace

Winter Park, Grand County, Colorado, United States
$228$189
per night
Outstanding(85 ratings)
$228$189
per night
View deal
Condo Winter Park
-18%
Jan 1 - Jan 8
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped wonderful condo with terrace | Mountain view

Winter Park, Grand County, Colorado, United States
$508$332
per night
Excellent(55 ratings)
$508$332
per night
View deal
House Winter Park
-77%
Sep 2 - Sep 9
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
$308$259
per night
Excellent(81 ratings)
$308$259
per night
View deal
House Winter Park
-34%
Apr 12 - Apr 19
House ∙ 12 guests ∙ 4 bedrooms

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

Winter Park, Grand County, Colorado, United States
$541$416
per night
Outstanding(29 ratings)
$541$416
per night
View deal
House Winter Park
-79%
Apr 26 - May 3
Free cancellation
House ∙ 14 guests ∙ 6 bedrooms

Vacation home with BBQ, heated pool & sauna | Lake view

Winter Park, Grand County, Colorado, United States
$3,289$702
per night
Outstanding(78 ratings)
$3,289$702
per night
View deal
House Winter Park
-82%
Apr 12 - Apr 19
House ∙ 8 guests ∙ 3 bedrooms

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

Winter Park, Grand County, Colorado, United States
$705$607
per night
Outstanding(19 ratings)
$705$607
per night
View deal
House Winter Park
-80%
May 24 - May 31
House ∙ 9 guests ∙ 3 bedrooms

Family-oriented wonderful vacation home with BBQ & patio | Pet-friendly

Winter Park, Grand County, Colorado, United States
$681$160
per night
Excellent(29 ratings)
$681$160
per night
View deal
House Winter Park
May 4 - May 11
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with terrace & jacuzzi | Mountain view

Winter Park, Grand County, Colorado, United States
$363
per night
Outstanding(92 ratings)
$363
per night
View deal
House Winter Park
-52%
Oct 11 - Oct 18
Free cancellation
House ∙ 16 guests ∙ 5 bedrooms

Family-friendly vacation home with jacuzzi, sauna & heated pool | River view | Perfect for remote work

Winter Park, Grand County, Colorado, United States
$1,776$881
per night
Outstanding(3 ratings)
$1,776$881
per night
View deal
House Winter Park
-77%
Apr 12 - Apr 19
House ∙ 8 guests ∙ 4 bedrooms

House with jacuzzi, patio & barbecue

Winter Park, Grand County, Colorado, United States
$1,730$464
per night
Outstanding(237 ratings)
$1,730$464
per night
View deal
House Winter Park
-84%
May 24 - May 31
House ∙ 12 guests ∙ 3 bedrooms

Family-oriented house with grill & terrace | Mountain view

Winter Park, Grand County, Colorado, United States
$990$290
per night
Outstanding(107 ratings)
$990$290
per night
View deal

Vacation Rentals With Fireplaces

House  Winter Park
May 3 - May 10
-81%
$3,182
$650
per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with hot tub & barbeque | Mountain view | Good for workation

Winter Park, Grand County, Colorado, United States
Fireplace
View deal
House  Winter Park
Apr 5 - Apr 12
-71%
$2,305
$677
per night
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with barbecue, terrace & jacuzzi | Mountain view

4.6
Excellent(97 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
House  Winter Park
Apr 15 - Apr 22
-40%
$990
$290
per night
House ∙ 12 guests ∙ 3 bedrooms

Family-oriented house with grill & terrace | Mountain view

5.0
Outstanding(107 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
See all offers

Apartments With Balconies or Patios

Apartment  Winter Park
Apr 5 - Apr 12
-70%
$1,137
$158
per night
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment with sauna & jacuzzi | Mountain view

Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House  Winter Park
Oct 4 - Oct 11
-56%
$1,776
$881
per night
House ∙ 16 guests ∙ 5 bedrooms

Family-friendly vacation home with jacuzzi, sauna & heated pool | River view | Perfect for remote work

5.0
Outstanding(3 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Balcony/Patio
View deal
House  Winter Park
Apr 15 - Apr 22
$604
per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with yard, BBQ & terrace | Mountain view

5.0
Outstanding(246 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
See all offers

Vacation rentals and apartments with air conditioning

Apartment  Winter Park
Nov 1 - Nov 8
-53%
$820
$138
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%
$794
$224
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%
$1,344
$374
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%

House Winter Park
May 3 - May 10
-46%
$2,851
$678
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%
$1,046
$207
per night
Apartment ∙ 9 guests ∙ 4 bedrooms

Apartment with Barbeque | Mountain View

Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
Apartment Winter Park
Nov 8 - Nov 15
-85%
$1,000
$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

5,179 unique rentals from 12 partner websites can be compared in Winter Park, with prices starting at $138 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
Mar 31 - Apr 7
$647
per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with grill, jacuzzi & patio | Nature view

5.0
Outstanding(122 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
Apr 26 - May 3
-25%
$937
$342
per night
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped big house with jacuzzi, patio & BBQ | Mountain view

4.9
Outstanding(59 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
Jun 14 - Jun 21
$468
per night
House ∙ 10 guests ∙ 5 bedrooms

House with patio, grill & jacuzzi | Mountain view

4.9
Outstanding(54 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
Jun 6 - Jun 13
-39%
$1,061
$382
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%
$1,970
$420
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
Jun 14 - Jun 21
-38%
$1,116
$269
per night
House ∙ 10 guests ∙ 4 bedrooms

House with Barbeque & Jacuzzi

5.0
Outstanding
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 $327
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 $127
per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.4
Very good(50 ratings)
Winter Park, Grand County, Colorado, United States
View deal

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Winter Park

  • Pet-friendly (749)
  • Pool (1,722)
  • Hot tub (3,148)
  • WiFi (4,921)
  • Fireplace (4,377)
  • Kitchen (4,813)
  • Washing machine (2,781)
  • TV (4,608)
  • Balcony/patio (1,431)
  • Parking (1,343)
  • No smoking (4,535)
  • Grill (1,953)

Winter Park is a good vacation spot if you want an accommodation with a pool, as 36% 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 $446 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 $1,158 (12/20 – 12/27) in Winter Park. Winter Park is most affordable in May (5/10 – 5/17), when average accommodation prices are $346 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 (1/10 – 1/17). It is easier to find a rental in a week of April (4/19 – 4/26), as only 29% 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 5,403 rentals
💳 Possible discounts up to 85%
🌙 Nightly prices starting at $127
⭐ Popular amenities Pets allowed, Pool and Hot tub
🐾 Pet friendly homes 808 homes
🏊 Vacation rentals with pools 1,946 homes
69,788 reviews
Winter Park vacation rentals have an average rating of 4.6/5 on 69,788 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 $127. Nightly prices for condos are $389 on average. House rentals in Winter Park cost on average $610 per night.

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

There are currently 5,403 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 1,946 vacation rentals available in Winter Park.

Are dogs allowed in vacation rentals in Winter Park?

Sure, there are 808 rentals in Winter Park that allow pets , with an average price of $497 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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