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Winter Park Vacation Rentals

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In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Winter Park

Exterior
A Frame Club

Cabin in Old Town Winter Park

3.5 star property
9.0 out of 10, Wonderful, (103)
"Unfortunately, our cabin looked directly into another cabin. River view was a very big stretch. There were no other rooms available so we were stuck with it. To make it worse, there are very bright lights on the building next door that were on all night, and since you cannot close the window due to the open design, we had a terrible nights sleep. A good idea in theory, but reality was a big miss. "
United States
Hannah
$229 nightly
The price is $259
Dec 4 - Dec 5
Total with taxes and fees
A Frame Club
Property entrance
Zephyr Mountain Lodge

Aparthotel in Winter Park Village

3.5 star property
8.2 out of 10, Very Good, (669)
"Zephyr is always a great choice! Located right in the square, this property is close to everything "
United States
Michelle
$342 nightly
The price is $387
Dec 4 - Dec 5
Total with taxes and fees
Zephyr Mountain Lodge
Exterior
Beautifully renovated 2 bedroom with clubhouse amenities

Condo in Fraser

2.0 star property
10.0 out of 10, Exceptional, (4)
"Updated 2 bedroom with mountain view. Everything was great! Recommend to anyone!"
United States
Brian B.
$285 nightly
The price is $303
Dec 4 - Dec 5
Total with taxes and fees
Beautifully renovated 2 bedroom with clubhouse amenities
Interior
River View Studio Near Winter Park Ski Resort

Condo in Fraser

9.6 out of 10, Exceptional, (4)
"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
$182 nightly
The price is $189
Dec 4 - Dec 5
Total with taxes and fees
River View Studio Near Winter Park Ski Resort
Property grounds
2 bedroom with new flooring & kitchen, private deck

Condo in Winter Park

9.8 out of 10, Exceptional, (7)
"Everything was nice and clean. Great location with lots of amenities near by. "
United States
Seung L.
$276 nightly
The price is $310
Dec 4 - Dec 5
Total with taxes and fees
2 bedroom with new flooring & kitchen, private deck
Flat-screen TV, fireplace
Updated 2 bedroom at Beaver Village with clubhouse amenities

Condo in Winter Park

10.0 out of 10, Exceptional, (3)
"Convenient to the slopes and town"
United States
Bradley H.
$250 nightly
The price is $281
Dec 7 - Dec 8
Total with taxes and fees
Updated 2 bedroom at Beaver Village with clubhouse amenities
Dining
This beautiful and modern condo is the ideal getaway in Winter Park.

Condo in Winter Park

2.0 star property
9.0 out of 10, Wonderful, (18)
"Loved the stay. Everything was great. "
United States
Shivali W.
$250 nightly
The price is $281
Dec 4 - Dec 5
Total with taxes and fees
This beautiful and modern condo is the ideal getaway in Winter Park.
Exterior
Fraser condo rental - 3 queens, full kitchen, private patio

Condo in Fraser

8.4 out of 10, Very Good, (12)
"Cute pics! Outside images of the building would have been helpful in finding the exact location.Overall clean and tidy... would be helpful to have a few basic cooking spices.Things that will help improve the quality and comfort would be a some better quality pillows and comforters or additional cozy blankets/throws. A bean bag in the main area would allow for additional comfort for anyone sitting on the floorBurners on the range need some additional attention or maintenance they seem to be...
United States
Ann Marie R.
$244 nightly
The price is $259
Dec 4 - Dec 5
Total with taxes and fees
Fraser condo rental - 3 queens, full kitchen, private patio
Fridge, microwave, oven, stovetop
Ideal and modern 1 bedroom - open floor plan and mt views

Condo in Fraser

9.4 out of 10, Exceptional, (13)
"Great property and location!"
United States
Sarah S.
$169 nightly
The price is $179
Dec 7 - Dec 8
Total with taxes and fees
Ideal and modern 1 bedroom - open floor plan and mt views
Terrace/patio
Modern Downtown Home w/ Private Sauna

Apartment in Downtown

2.0 star property
10.0 out of 10, Exceptional, (10)
"Excellent Property. Upgraded amenities, close to restaurants, grocery store, and Amtrak Station. ."
United States
Ronnie S.
$247 nightly
The price is $275
Dec 7 - Dec 8
Total with taxes and fees
Modern Downtown Home w/ Private Sauna
Property grounds
Spacious 2 bedroom condo remodeled kitchen, vaulted ceilings

Condo in Winter Park

9.6 out of 10, Exceptional, (9)
"This is a perfect spot for a summer mountain getaway. Close to downtown Fraser and the bike path is right across the highway. Highly recommended!"
United States
Heather
$250 nightly
The price is $281
Dec 4 - Dec 5
Total with taxes and fees
Spacious 2 bedroom condo remodeled kitchen, vaulted ceilings
Property grounds
Recently remodeled for top notch comfort!

Condo in Winter Park

10.0 out of 10, Exceptional, (12)
"This is a nice property to stay for a couple of nights. It has all your basic needs for a stay."
United States
Diane H.
$278 nightly
The price is $311
Dec 4 - Dec 5
Total with taxes and fees
Recently remodeled for top notch comfort!
Dining
Fraser Condo Near Tubing Hill!

Condo in Fraser

9.6 out of 10, Exceptional, (41)
"Great location for all snow activities"
United States
Kayla S.
$307 nightly
The price is $341
Dec 4 - Dec 5
Total with taxes and fees
Fraser Condo Near Tubing Hill!
Terrace/patio
Renovated Condo near the Slopes and Trails

Condo in Winter Park

9.4 out of 10, Exceptional, (171)
"It was a great pace for our family to stay, the pool access was great"
United States
Natasha M.
$324 nightly
The price is $364
Dec 5 - Dec 6
Total with taxes and fees
Renovated Condo near the Slopes and Trails
Fridge, microwave, oven, stovetop
New 1 Bedroom, downtown location & lots of amenities!

Condo in Winter Park

9.6 out of 10, Exceptional, (12)
"Beautiful little place, updated and great view of the mountains from the living room, close to everything in town. Would definitely stay again."
United States
Denver C.
$189 nightly
The price is $212
Dec 4 - Dec 5
Total with taxes and fees
New 1 Bedroom, downtown location & lots of amenities!
Exterior
Updated interior in this 1 bedroom, private patio

Condo in Fraser

9.4 out of 10, Exceptional, (28)
"We enjoyed our stay"
United States
Caleb M.
$171 nightly
The price is $182
Dec 4 - Dec 5
Total with taxes and fees
Updated interior in this 1 bedroom, private patio
Iron/ironing board, free WiFi, bed sheets
Modern slopeside out studio with access to hot tub, fire pit & fire place

Condo in Winter Park Village

9.4 out of 10, Exceptional, (24)
"All we needed for a great time at WP"
United States
Frank M.
$267 nightly
The price is $298
Dec 6 - Dec 7
Total with taxes and fees
Modern slopeside out studio with access to hot tub, fire pit & fire place
Fridge, microwave, stovetop, dishwasher
Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort

Condo in Winter Park Village

9.8 out of 10, Exceptional, (86)
"Great views and very clean. "
United States
Gregory
$251 nightly
The price is $282
Dec 4 - Dec 5
Total with taxes and fees
Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort
Outdoor pool, a heated pool
Cozy Retreat Across from the Clubhouse - 2bd/2ba Condo (Sleeps 6)

Condo in Fraser

10.0 out of 10, Exceptional, (111)
"Thanks for an easy, lovely stay!"
United States
Samantha L.
$307 nightly
The price is $326
Dec 4 - Dec 5
Total with taxes and fees
Cozy Retreat Across from the Clubhouse - 2bd/2ba Condo (Sleeps 6)
Exterior detail
Pet friendly 2 bedroom, walk to Main Street, forest view

Condo in Winter Park

9.8 out of 10, Exceptional, (24)
"We had a great stay, enjoyed the property and location."
United States
Kathleen C.
$325 nightly
The price is $365
Dec 4 - Dec 5
Total with taxes and fees
Pet friendly 2 bedroom, walk to Main Street, forest view
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

Zephyr Mountain Lodge

Zephyr Mountain Lodge

10/10 Excellent
"Clean, convenient and easy. All staff members are very friendly. We'll see"
jay 15-night trip
Posted 2 days ago
Zephyr Mountain Lodge

Price trends for vacation rentals in Winter Park

Less expensive
More expensive
This month
Next month
November
March
$377
$372
Month
Price
January
$372
February
$427
March
$465
April
$264
May
$262
June
$281
July
$336
August
$291
September
$246
October
$207
November
$205
December
$377
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 $209 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?

7 BR home in central Winter Park with great views on bus route: This highly rated vacation home rental in Winter Park is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 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 Beautiful Ski-In Home, with Hot Tub! and Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus....

How many vacation rentals are there in Winter Park?

With 322 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.