Winter Park Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Winter Park vacation rentals

Interior

River View Studio Near Winter Park Ski Resort

River View Studio Near Winter Park Ski Resort
Fraser
9.6 out of 10, Exceptional, (4 reviews)
"Very good communication through the entirety of the stay. room is all you really need for one person and it is well maintained. view is great, would stay again. "
United States
Carson
$186 nightly
The price is $193
Jan 22 - Jan 23
Total with taxes and fees
River View Studio Near Winter Park Ski Resort
Property grounds

Inviting ski-in/ski-out condo hot tub, gas fireplace, and firepit

Inviting ski-in/ski-out condo hot tub, gas fireplace, and firepit
Winter Park Village
8.8 out of 10, Excellent, (29 reviews)
"Clean, PLENTY of everything you need + backups, perfect location (village / slopes), and more! "
United States
David
$250 nightly
The price is $280
Jan 25 - Jan 26
Total with taxes and fees
Inviting ski-in/ski-out condo hot tub, gas fireplace, and firepit
Apartment (0 Bedroom) | Interior

Walk to Dtwn: Winter Park Studio w/ Hot Tub Access

Walk to Dtwn: Winter Park Studio w/ Hot Tub Access
3.0 star property
Winter Park
$247 nightly
The price is $280
Jan 19 - Jan 20
Total with taxes and fees
Walk to Dtwn: Winter Park Studio w/ Hot Tub Access
Terrace/patio

Modern Downtown Home w/ Private Sauna

Modern Downtown Home w/ Private Sauna
2.0 star property
Downtown
10.0 out of 10, Exceptional, (11 reviews)
"Excellent Property. Upgraded amenities, close to restaurants, grocery store, and Amtrak Station. ."
United States
Ronnie S.
$234 nightly
The price is $260
Jan 19 - Jan 20
Total with taxes and fees
Modern Downtown Home w/ Private Sauna
Exterior

Peaks + Pines + Playtime | Your Iconic Retreat

Peaks + Pines + Playtime | Your Iconic Retreat
2.0 star property
Rendezvous
9.6 out of 10, Exceptional, (4 reviews)
"Girls weekend for a 50th- perfect for hiking, easy into town, so much space for storage, sleep, and cooking. Definitely the perfect place for our group "
United States
Elizabeth M.
$547 nightly
The price is $566
Jan 20 - Jan 21
Total with taxes and fees
Peaks + Pines + Playtime | Your Iconic Retreat
Exterior

Cozy Pet & Family-Friendly Condo Near Winter Park•Heated Garage•Trails•Sleeps 6

Cozy Pet & Family-Friendly Condo Near Winter Park•Heated Garage•Trails•Sleeps 6
Fraser
9.8 out of 10, Exceptional, (49 reviews)
"Everything was as expected, would stay again!"
United States
Andres E.
$320 nightly
The price is $339
Jan 20 - Jan 21
Total with taxes and fees
Cozy Pet & Family-Friendly Condo Near Winter Park•Heated Garage•Trails•Sleeps 6
Terrace/patio

Fraser Condo Near Tubing Hill!

Fraser Condo Near Tubing Hill!
Fraser
9.6 out of 10, Exceptional, (42 reviews)
"Great location for all snow activities"
United States
Kayla S.
$316 nightly
The price is $351
Jan 19 - Jan 20
Total with taxes and fees
Fraser Condo Near Tubing Hill!
Exterior

Madge’s Studio - Pets Welcome

Madge’s Studio - Pets Welcome
Fraser
10.0 out of 10, Exceptional, (104 reviews)
"I was actually not able to make it but did appreciate a quick response from owner, "
United States
Scott
$147 nightly
The price is $163
Jan 25 - Jan 26
Total with taxes and fees
Madge’s Studio - Pets Welcome
Fridge, microwave, oven, stovetop

2 bedroom with new flooring & kitchen, private deck

2 bedroom with new flooring & kitchen, private deck
Winter Park
9.8 out of 10, Exceptional, (7 reviews)
"Everything was nice and clean. Great location with lots of amenities near by. "
United States
Seung L.
$320 nightly
The price is $359
Jan 19 - Jan 20
Total with taxes and fees
2 bedroom with new flooring & kitchen, private deck
TV, fireplace, computer monitors

Beautifully renovated 2 bedroom with clubhouse amenities

Beautifully renovated 2 bedroom with clubhouse amenities
2.0 star property
Fraser
10.0 out of 10, Exceptional, (4 reviews)
"Updated 2 bedroom with mountain view. Everything was great! Recommend to anyone!"
United States
Brian B.
$336 nightly
The price is $356
Jan 20 - Jan 21
Total with taxes and fees
Beautifully renovated 2 bedroom with clubhouse amenities
Property entrance

Zephyr Mountain Lodge

Zephyr Mountain Lodge
3.5 star property
Winter Park Village
8.2 out of 10, Very Good, (678 reviews)
"Clean room and staff was outstanding. "
United States
Jessica
$552 nightly
The price is $625
Jan 19 - Jan 20
Total with taxes and fees
Zephyr Mountain Lodge
TV, fireplace

This beautiful and modern condo is the ideal getaway in Winter Park.

This beautiful and modern condo is the ideal getaway in Winter Park.
2.0 star property
Winter Park
9.0 out of 10, Wonderful, (20 reviews)
"Very nice condo in a great location to shopping and restaurants. We only stayed two nights but enjoyed our stay and would definitely stay here again. "
United States
Dana B.
$292 nightly
The price is $327
Jan 19 - Jan 20
Total with taxes and fees
This beautiful and modern condo is the ideal getaway in Winter Park.
Exterior

Fraser Crossing 3227 Ski In Ski Out Winter Park Resort

Fraser Crossing 3227 Ski In Ski Out Winter Park Resort
Winter Park Village
8.4 out of 10, Very Good, (15 reviews)
"Great stay! Loved the location. Easy to take a lunch break and get back out on the slopes quickly. Just a quick few steps to the Gondola. Enjoyed our stay!"
United States
Limin K.
$300 nightly
The price is $337
Jan 19 - Jan 20
Total with taxes and fees
Fraser Crossing 3227 Ski In Ski Out Winter Park Resort
1 bedroom, free WiFi, bed sheets

Micro Guest Suite Downtown Winter Park GREAT LOCATION

Micro Guest Suite Downtown Winter Park GREAT LOCATION
Winter Park
9.8 out of 10, Exceptional, (14 reviews)
"Perfect location to hop on a bus to go to the resort or walk down the street to grab a bite to eat. Trailheads are close by. Very functional, modern, efficient. Enjoyed the hot tub after a day on the slopes. Highly recommended, would stay there again in a heartbeat!"
United States
Sarah
$226 nightly
The price is $254
Jan 19 - Jan 20
Total with taxes and fees
Micro Guest Suite Downtown Winter Park GREAT LOCATION
Pool

Super modern interior, walk to downtown, clubhouse amenities

Super modern interior, walk to downtown, clubhouse amenities
WINTER PARK
8.2 out of 10, Very Good, (13 reviews)
"perfect for a small group look to ski"
United States
Mackenzie M.
$199 nightly
The price is $224
Jan 19 - Jan 20
Total with taxes and fees
Super modern interior, walk to downtown, clubhouse amenities
TV, fireplace, DVD player

Updated interior in this 1 bedroom, private patio

Updated interior in this 1 bedroom, private patio
Fraser
9.4 out of 10, Exceptional, (28 reviews)
"We enjoyed our stay"
United States
Caleb M.
$208 nightly
The price is $221
Jan 19 - Jan 20
Total with taxes and fees
Updated interior in this 1 bedroom, private patio
Property grounds

Ski Mountain Condo, located in Winter Park Resort's Founder's Pointe Building, I

Ski Mountain Condo, located in Winter Park Resort's Founder's Pointe Building, I
2.0 star property
Winter Park Village
9.6 out of 10, Exceptional, (27 reviews)
"Wonderfully convenient!"
United States
Brandonlee M.
$417 nightly
The price is $469
Jan 19 - Jan 20
Total with taxes and fees
Ski Mountain Condo, located in Winter Park Resort's Founder's Pointe Building, I
Exterior

Winterpark Cozy slope side condo

Winterpark Cozy slope side condo
Winter Park Village
8.8 out of 10, Excellent, (13 reviews)
"Enjoyed the stay quite a bit. Great location and just a 10 min walk to the base. Place was clean and well equipped. Only downsides for me was the bedding (strong chemical detergent smell on linens, and pillows could use a refresh), and had to pay for parking. Would probably stay here again."
United States
David R.
$231 nightly
The price is $259
Jan 19 - Jan 20
Total with taxes and fees
Winterpark Cozy slope side condo
TV, fireplace, DVD player

New Listing Remodeled 1 Bedroom vaulted ceiling & private deck

New Listing Remodeled 1 Bedroom vaulted ceiling & private deck
Winter Park
9.6 out of 10, Exceptional, (25 reviews)
"Very nice place to stay on our last minute trip."
United States
Katie W.
$209 nightly
The price is $234
Jan 19 - Jan 20
Total with taxes and fees
New Listing Remodeled 1 Bedroom vaulted ceiling & private deck
Smart TV, fireplace, DVD player, books

2BD Condo on the river, walk to town, free ski bus!

2BD Condo on the river, walk to town, free ski bus!
Winter Park
9.2 out of 10, Wonderful, (44 reviews)
"Quiet with babbling stream, walking trail right out front door, and walking distance into downtown Winter Park. Love this location every time!"
United States
Steve B.
$265 nightly
The price is $297
Feb 3 - Feb 4
Total with taxes and fees
2BD Condo on the river, walk to town, free ski bus!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Park Hotel Reviews

Ultimate Luxury Ski Chalet | Casa de Montana | Hot Tub, Vintage Video Games & More!

Ultimate Luxury Ski Chalet | Casa de Montana | Hot Tub, Vintage Video Games & More!

10/10 Excellent
"Best home ever!!!! "
Chiara C. 3-night trip
Posted 4 days ago
Ultimate Luxury Ski Chalet | Casa de Montana | Hot Tub, Vintage Video Games & More!

Price trends for vacation rentals in Winter Park

Less expensive
More expensive
Next month
November
March
$374
Month
Price
January
$297
February
$374
March
$432
April
$285
May
$278
June
$285
July
$343
August
$312
September
$319
October
$291
November
$267
December
$380
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Winter Park. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Winter Park

Everything you need to know about Winter Park vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter Park vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter Park vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter Park vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter Park. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter Park in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $280 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter Park rentals

At Expedia, we put the best Winter Park vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter Park vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winter Park?

Yes, we give you a choice of vacation rentals in Winter Park close to Amaze'n Maze Winter Park, or you can select a more remote option if you want a relaxing stay. Visitors like the ski slopes and majestic mountain landscape in Winter Park. You can also check out the live music while you're visiting.

What are some of the best vacation home rentals that Winter Park has to offer?

Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22: This highly rated vacation home rental in Winter Park is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Winter Park are Ski In Out Condo I Huge Hot Tub I Great Views I Heated Garage I Discounted Attractions and Ski In Out Chalet 277 I Hot Tub I Theatre I Views I Game Room I Discounted Attractions.

How many vacation rentals are there in Winter Park?

With 357 Expedia vacation rentals, you're sure to find just the right place for your Winter Park stay.

What’s there to see and do in Winter Park?

The Fraser River Trail and Arapaho National Recreation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Amaze'n Maze Winter Park. While here, Winter Park Ski Resort and Trestle Bike Park are other places worth a visit.

What’s a vacation rental in Winter Park like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winter Park. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.