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

Vacation rentals in Winter Park

Find 5,348 available house rentals from 14 partners
Anytime
Guests
Anytime
Guests

  • 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 $77 per night!

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
$1,465$351
per night
Excellent(17 ratings)
$1,465$351
per night
View deal
House Winter Park
-19%
Jun 22 - Jun 29
House ∙ 16 guests ∙ 6 bedrooms

Children-friendly charming house with barbecue, pool & terrace | Mountain view | Dogs allowed

Winter Park, Grand County, Colorado, United States
$1,050$848
per night
$1,050$848
per night
View deal
Apartment Winter Park
-80%
Apr 26 - May 3
Apartment ∙ 10 guests ∙ 4 bedrooms

Children-friendly big rental apartment with BBQ, pool & hot tub | Mountain view

Winter Park, Grand County, Colorado, United States
$1,594$326
per night
Outstanding(3 ratings)
$1,594$326
per night
View deal
House Winter Park
-82%
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
$505$89
per night
Excellent(29 ratings)
$505$89
per night
View deal
Cabin Winter Park
-74%
Apr 25 - May 2
Cabin ∙ 16 guests ∙ 6 bedrooms

Cabin with patio, barbecue & hot tub

Winter Park, Grand County, Colorado, United States
$2,077$542
per night
Excellent(101 ratings)
$2,077$542
per night
View deal
Condo Winter Park
-65%
Sep 23 - Sep 30
Condo ∙ 8 guests ∙ 3 bedrooms

Child-friendly condo with pool, patio & barbecue | Mountain view

Winter Park, Grand County, Colorado, United States
$500$175
per night
Outstanding(39 ratings)
$500$175
per night
View deal
House Winter Park
-64%
Jul 26 - Aug 2
House ∙ 16 guests ∙ 5 bedrooms

Vacation home with hot tub, barbecue & yard

Winter Park, Grand County, Colorado, United States
$1,184$421
per night
Outstanding(88 ratings)
$1,184$421
per night
View deal
Condo Winter Park
May 17 - May 24
Condo ∙ 8 guests ∙ 3 bedrooms

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

Winter Park, Grand County, Colorado, United States
$130
per night
Outstanding(29 ratings)
$130
per night
View deal
Condo Winter Park
Dec 27 - Jan 3
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped wonderful condo with terrace | Mountain view

Winter Park, Grand County, Colorado, United States
$400
per night
Excellent(54 ratings)
$400
per night
View deal
House Winter Park
-63%
Jun 22 - Jun 29
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
$1,530$567
per night
Excellent(27 ratings)
$1,530$567
per night
View deal
House Winter Park
Feb 14 - Feb 21
House ∙ 11 guests ∙ 4 bedrooms

House with BBQ & jacuzzi | Mountain view

Winter Park, Grand County, Colorado, United States
$686
per night
Outstanding(13 ratings)
$686
per night
View deal
Apartment Winter Park
-83%
May 3 - May 10
Apartment ∙ 4 guests ∙ 1 bedroom

Apartment with hot tub & heated pool | Mountain view

Winter Park, Grand County, Colorado, United States
$537$89
per night
Outstanding(1 rating)
$537$89
per night
View deal
Condo Winter Park
-73%
May 10 - May 17
Condo ∙ 6 guests ∙ 2 bedrooms

Child-friendly condo with heated pool, patio & jacuzzi | Pet-friendly

Winter Park, Grand County, Colorado, United States
$449$120
per night
Outstanding(67 ratings)
$449$120
per night
View deal
Condo Winter Park
-26%
Feb 14 - Feb 21
Condo ∙ 4 guests ∙ 1 bedroom

Child-friendly condo with pool & jacuzzi | Pets allowed

Winter Park, Grand County, Colorado, United States
$202$150
per night
Very good(35 ratings)
$202$150
per night
View deal
House Winter Park
-57%
Jul 2 - Jul 9
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly vacation home with jacuzzi | Mountain view

Winter Park, Grand County, Colorado, United States
$488$209
per night
Outstanding(15 ratings)
$488$209
per night
View deal

Vacation Rentals With Fireplaces

House Winter Park
Apr 23 - Apr 30
-85%
$587
$89
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
Apartment Winter Park
May 3 - May 10
-86%
$1,270
$178
per night
Apartment ∙ 10 guests ∙ 3 bedrooms

Family-friendly apartment with patio, BBQ & jacuzzi | Mountain view | Pets are welcome

4.8
Outstanding(55 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
House Winter Park
Apr 26 - May 3
-74%
$2,306
$591
per night
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with barbecue, terrace & jacuzzi | Mountain view

4.6
Excellent(101 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
See all offers

Vacation houses with Balconies or Patios

House Winter Park
Sep 23 - Sep 30
-69%
$783
$245
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
Sep 23 - Sep 30
-56%
$764
$336
per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation home with patio, grill & hot tub

4.9
Outstanding(30 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House Winter Park
Apr 26 - May 3
-79%
$1,185
$255
per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with BBQ & terrace | Mountain view

4.5
Excellent(161 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
See all offers

Vacation Rentals With Saunas

Apartment Winter Park
Apr 26 - May 3
-90%
$736
$77
per night
Apartment ∙ 7 guests ∙ 2 bedrooms

Apartment with pool, jacuzzi & BBQ | Mountain view

5.0
Outstanding(1 rating)
Winter Park, Grand County, Colorado, United States
Sauna
View deal
House Winter Park
Apr 26 - May 3
-78%
$1,992
$439
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with hot tub, barbecue & heated pool | River view

5.0
Outstanding(2 ratings)
Winter Park, Grand County, Colorado, United States
Sauna
View deal
Apartment Winter Park
May 10 - May 17
-84%
$725
$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
See all offers

Best Vacation Home Deals in Winter Park

Save up to 91%

Apartment Winter Park
May 10 - May 17
-90%
$780
$82
per night
Apartment ∙ 7 guests ∙ 2 bedrooms

Holiday apartment with pool, barbeque & hot tub

5.0
Outstanding(1 rating)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
Jun 28 - Jul 5
-59%
$388
$161
per night
House ∙ 11 guests ∙ 2 bedrooms

Children-friendly vacation home | Pet-friendly

3.8
Good(13 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Apartment Winter Park
Apr 26 - May 3
-91%
$955
$89
per night
Apartment ∙ 4 guests ∙ 1 bedroom

Rental apartment with pool & jacuzzi

4.6
Excellent(87 ratings)
Winter Park, Grand County, Colorado, United States
View deal

5,348 unique rentals from 13 partner websites can be compared in Winter Park, with prices starting at $77 a night. Every one of the properties from the different providers are directly compared by our algorithm so you can save up to 84%.

Budget-friendly Vacation Rentals in Winter Park

Find Fantastic yet Inexpensive Offers

House Winter Park
Sep 1 - Sep 8
-62%
$503
$191
per night
House ∙ 8 guests ∙ 2 bedrooms

Vacation home with 2 rooms for 8 persons

4.9
Outstanding(32 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
Oct 13 - Oct 20
-57%
$505
$219
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
View deal
Studio flat Winter Park
Jun 14 - Jun 21
-74%
$277
$71
per night
Studio flat ∙ 4 guests ∙ 1 bedroom

Family-friendly nice studio with hot tub | Close to the ski

4.5
Excellent(36 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
Sep 23 - Sep 30
-89%
$850
$97
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Condo with hot tub | Mountain view

4.9
Outstanding(166 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
Sep 23 - Sep 30
-74%
$614
$159
per night
House ∙ 9 guests ∙ 4 bedrooms

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

4.7
Excellent(82 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Apartment Winter Park
Apr 26 - May 3
-82%
$1,976
$356
per night
Apartment ∙ 8 guests ∙ 3 bedrooms

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

4.9
Outstanding(54 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 $303
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(49 ratings)
Winter Park, Grand County, Colorado, United States
View deal

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Find your dream stay

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

Popular Rental Amenities in Winter Park

  • Pet-friendly (776)
  • Pool (1,831)
  • Hot tub (2,890)
  • WiFi (5,048)
  • Fireplace (4,451)
  • Kitchen (4,908)
  • Washing machine (2,929)
  • TV (4,676)
  • Balcony/patio (1,463)
  • Parking (1,543)
  • No smoking (4,774)
  • Grill (2,082)

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 $472 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 $602 (1/31 – 2/7) in Winter Park. Winter Park is most affordable in May (5/10 – 5/17), when average accommodation prices are $485 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 32% 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 5,348 rentals
💳 Possible discounts up to 84%
🌙 Nightly prices starting at $77
⭐ Popular amenities Pets allowed, Pool and Hot tub
🐾 Pet friendly homes 789 homes
🏊 Vacation rentals with pools 1,852 homes
70,986 reviews
Winter Park vacation rentals have an average rating of 4.6/5 on 70,986 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 $77. Nightly prices for condos are $424 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 5,348 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 1,852 vacation rentals available in Winter Park.

Are dogs allowed in vacation rentals in Winter Park?

Sure, there are 789 rentals in Winter Park that allow pets , with an average price of $499 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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