
Photo by Kayla Templin
Old Town Winter Park vacation rentals
We found 582 vacation rentals — enter your dates for availability
Select from 30 houses, 31 condos, and other vacation rentals to find the perfect place for your stay in Old Town Winter Park. Vacation rentals offer the amenities you expect for you and your friends, family, or even pets, such as WiFi and a hot tub. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Old Town Winter Park
Showing deals for:Aug 1 - Aug 8
Image gallery for Winter Park Ski in/out XXL ZML condo w/ views of ski hill, gondola, base, river

1010 out of 10 rating
Exceptional
(29 reviews)
Winter Park Ski in/out XXL ZML condo w/ views of ski hill, gondola, base, river
Winter Park, CO
10% off
Price is $315
$315
$2,662 total
$2,662 total
Image gallery for Base Camp-Play hard then rest extravagantly! Ski in/out 4 BR-secluded-Jane Creek

1010 out of 10 rating
Exceptional
(113 reviews)
Base Camp-Play hard then rest extravagantly! Ski in/out 4 BR-secluded-Jane Creek
Winter Park, CO
10% off
Price is $806
$806
$7,119 total
$7,119 total
Image gallery for Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort

9.89.8 out of 10 rating
Exceptional
(85 reviews)
Top Floor Ski-In / Ski-Out Studio Condo at the base of Winter Park Resort
Winter Park, CO
10% off
Price is $140
$140
$1,339 total
$1,339 total
Image gallery for 1 BR sleeps 5. Walk to the Gondola! Woods & Fraser River off the back deck.

1010 out of 10 rating
Exceptional
(48 reviews)
1 BR sleeps 5. Walk to the Gondola! Woods & Fraser River off the back deck.
Winter Park, CO
10% off
Price is $148
$148
$1,282 total
$1,282 total
Image gallery for 3 bed/3 ba Townhouse: hot tub, amazing view and on shuttle route

1010 out of 10 rating
Exceptional
(8 reviews)
3 bed/3 ba Townhouse: hot tub, amazing view and on shuttle route
Winter Park, CO
10% off
Price is $360
$360
$3,092 total
$3,092 total
Image gallery for Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Modern Condo at Iron Horse - Ski In / Ski Out, Sleeps 4
Winter Park, CO
10% off
Price is $315
$315
$2,617 total
$2,617 total
Image gallery for Ski-in Ski-Out Zephyr Mountain Lodge Condo with Hot Tub next to Gondola

9.69.6 out of 10 rating
Exceptional
(44 reviews)
Ski-in Ski-Out Zephyr Mountain Lodge Condo with Hot Tub next to Gondola
Winter Park, CO
10% off
Price is $250
$250
$2,071 total
$2,071 total
Image gallery for NEW! Luxury Penthouse 4BR/3BA Condo In Heart Of Downtown Winter Park

1010 out of 10 rating
Exceptional
(6 reviews)
NEW! Luxury Penthouse 4BR/3BA Condo In Heart Of Downtown Winter Park
Winter Park, CO
10% off
Price is $1,021
$1,021
$8,469 total
$8,469 total
Image gallery for Beautiful Ski In/Ski Out Studio Condo NO CLEANING FEES

9.89.8 out of 10 rating
Exceptional
(105 reviews)
Beautiful Ski In/Ski Out Studio Condo NO CLEANING FEES
Winter Park, CO
10% off
Price is $113
$113
$888 total
$888 total
Image gallery for New Listing Ski-In/Ski-Out Zephyr 1 Bedroom Condo at the base of Winter Park

1010 out of 10 rating
Exceptional
(85 reviews)
New Listing Ski-In/Ski-Out Zephyr 1 Bedroom Condo at the base of Winter Park
Winter Park, CO
10% off
Price is $160
$160
$1,497 total
$1,497 total
Image gallery for Ski-in ski-out, Modern Condo, Gourmet Kitchen, Great Amenities, Free Garage +EV!

1010 out of 10 rating
Exceptional
(34 reviews)
Ski-in ski-out, Modern Condo, Gourmet Kitchen, Great Amenities, Free Garage +EV!
Winter Park, CO
10% off
Price is $330
$330
$2,780 total
$2,780 total
Image gallery for Platinum Top Floor | Ski-in/Ski-out | WP Resort

9.89.8 out of 10 rating
Exceptional
(13 reviews)
Platinum Top Floor | Ski-in/Ski-out | WP Resort
Winter Park, CO
10% off
Price is $155
$155
$1,491 total
$1,491 total
Image gallery for Walk to the base! Inside the WP gates! Complete Remodel w/private hot tub

1010 out of 10 rating
Exceptional
(52 reviews)
Walk to the base! Inside the WP gates! Complete Remodel w/private hot tub
Winter Park, CO
10% off
Price is $315
$315
$2,701 total
$2,701 total
Image gallery for Completely Updated Condo in Great Location only steps to the Gondola

9.89.8 out of 10 rating
Exceptional
(142 reviews)
Completely Updated Condo in Great Location only steps to the Gondola
Winter Park, CO
10% off
Price is $107
$107
$998 total
$998 total
Image gallery for Private Hot Tub, Fire Pit, outdoor grill & views of the ski runs! >STR#008934

1010 out of 10 rating
Exceptional
(55 reviews)
Private Hot Tub, Fire Pit, outdoor grill & views of the ski runs! >STR#008934
Winter Park, CO
10% off
Price is $405
$405
$3,474 total
$3,474 total
Image gallery for MODERN NEW BUILD IN WINTER PARK-steps from trail.beautiful ski in out.1 br+den.

1010 out of 10 rating
Exceptional
(10 reviews)
MODERN NEW BUILD IN WINTER PARK-steps from trail.beautiful ski in out.1 br+den.
Winter Park, CO
5% off
Price is $88
$88
$841 total
$841 total
Image gallery for WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH & CARPET

1010 out of 10 rating
Exceptional
(129 reviews)
WP Base! Zephyr Mtn Ldge 1BR Ski In/Out, Smart TVs, solo WiFi, NEW BATH & CARPET
Winter Park, CO
10% off
Price is $95
$95
$968 total
$968 total
Image gallery for Winter Park Townhome w/ Stunning Slope Views!

1010 out of 10 rating
Exceptional
(34 reviews)
Winter Park Townhome w/ Stunning Slope Views!
Winter Park, CO
10% off
Price is $360
$360
$3,134 total
$3,134 total
Image gallery for Spectacular Mountain Retreat

1010 out of 10 rating
Exceptional
(5 reviews)
Spectacular Mountain Retreat
Winter Park, CO
10% off
Price is $225
$225
$1,950 total
$1,950 total
Image gallery for True ski in out. -do not hit request to book without asking please

1010 out of 10 rating
Exceptional
(122 reviews)
True ski in out. -do not hit request to book without asking please
Winter Park, CO
10% off
Price is $199
$199
$1,868 total
$1,868 total
Image gallery for Amenities Deck Level | Walk to Gondola | WP Resort

9.89.8 out of 10 rating
Exceptional
(58 reviews)
Amenities Deck Level | Walk to Gondola | WP Resort
Winter Park, Colorado
10% off
Price is $175
$175
$1,680 total
$1,680 total
Image gallery for Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark

9.89.8 out of 10 rating
Exceptional
(44 reviews)
Spectacular Views! Luxury 3BR/2BA in Base Area Location - Trademark
Winter Park, CO
14% off
Price is $300
$300
$2,696 total
$2,696 total
Image gallery for WP Resort Village | Amenity Deck Level | Fireplace
![[The Condo] Beautifully appointed 1 king bed / 1 bath with full kitchen](https://images.trvl-media.com/lodging/73000000/72600000/72594800/72594788/w600h397x0y3-ef97122b.jpg?impolicy=fcrop&w=600&h=400&p=1&q=high)
9.69.6 out of 10 rating
Exceptional
(15 reviews)
WP Resort Village | Amenity Deck Level | Fireplace
Winter Park, CO
10% off
Price is $178
$178
$1,679 total
$1,679 total
Image gallery for 3 BR with Private Hot Tub and views of the slopes in prestigious Lakota!!

1010 out of 10 rating
Exceptional
(97 reviews)
3 BR with Private Hot Tub and views of the slopes in prestigious Lakota!!
Winter Park, CO
15% off
Price is $225
$225
$1,936 total
$1,936 total
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Old Town Winter Park
Beautiful Condo - Riverfront-Slopeside-Walk to Resort-On Bus Route
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
113 reviews(113 reviews)
Spacious condo just moments from Winter Park Ski Resort w/shared hot tub
Sleeps 10 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
Slope side Single Family Home at the base of Winter Park!
Sleeps 14 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Dog-friendly retreat with private hot tub & mountain view - near skiing/hiking
Sleeps 6 · 1 bedroom · 1 bathroom
6.06.0 out of 10
3 reviews(3 reviews)
♥ Slopeside Retreat | Large & Built For Families | Sleeps 17! | Ski Hill Views
Sleeps 17 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
New Ground Level Riverfront Suite - Walk to Village!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
135 reviews(135 reviews)
Top rated rentals - Old Town Winter Park
A Wonderful Place to Stay
1010 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
As always, amazing.
1010 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
Spring Break
1010 out of 10
Exceptionalexceptional
162 reviews(162 reviews)
Spring Break Family Fun
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Great Location and Excellent Hosts
1010 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Convenient Stay
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Beautiful condo close to the slopes
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Excellent Property
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental accommodation in Old Town Winter Park?
Condos are the most popular kind of vacation rental in Old Town Winter Park, according to our data. Even if you’ve got something else in mind, Vrbo has vacation homes in loads of sizes and shapes. Filter our options to find your perfect Old Town Winter Park pad.
How much does it cost to rent a vacation rental in Old Town Winter Park?
Season, property type and length of stay are some of the conditions that can determine the price of a vacation home. Simply click on your travel dates to find the ultimate escape. From cozy cabins to sprawling villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Old Town Winter Park?
Prices for beach houses in Old Town Winter Park vary depending on the style and size of the property and time of year you’re traveling. Simply enter your dates of travel into Vrbo and how many guests to see available options and prices. From there you can use our filter tool to refine your search results by ratings, amenities and more.
Are there pet-friendly vacation rentals in Old Town Winter Park?
Pack a suitcase and a bone for your beloved pooch because Old Town Winter Park has 48 properties that roll out the welcome mat to pets. Let your happy hound join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check our “Pets allowed” filter box.
Can I rent a house with a pool in Old Town Winter Park?
Pack your swimsuit and pool noodle, because there are 18 houses with a private pool in Old Town Winter Park. Book a stay at one of these superb vacation homes and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Old Town Winter Park?
When it comes to rental amenities that guests are on the lookout for in Old Town Winter Park, ski-in/ski-out facilities, tennis and a firepit rank highest. With Vrbo vacation rentals, there are choices to suit your taste and style, whether you’re planning to get away with relatives, friends or even pets.
Are there large group vacation rentals in Old Town Winter Park?
Old Town Winter Park has 25 vacation properties that can fit 10 or more people. These stays come with all the space you need to enjoy good times with friends and family.
Are there vacation rentals in Old Town Winter Park that welcome kids?
With 48 family-friendly vacation properties available in Old Town Winter Park, now is an awesome time to introduce your kids to the magic of travel. Simply check our “Properties good for families” filter box to discover stays packed with conveniences perfect for traveling families, like dining rooms, yards, entertainment units and bunk beds.
Are there one-bedroom vacation rentals in Old Town Winter Park?
Old Town Winter Park has four one-bedroom rentals on offer. Often positioned in prime areas due to their compact size, a one-bedroom vacation rental is perfect if you’re getting away with a buddy or your partner. And with home comforts such as laundry facilities and more privacy than a standard hotel, you’ll be able to chill out while enjoying this fantastic destination.
Can I find two-bedroom vacation rentals in Old Town Winter Park?
Old Town Winter Park has seven two-bedroom vacation properties to choose from. Book a vacation home with all the privacy and space you’re looking for at a price that won’t break the bank on Vrbo.
Are there vacation rentals with WiFi in Old Town Winter Park?
You’ll have a choice of 17 vacation rentals with WiFi in Old Town Winter Park. If you’d like to disconnect from the world on your escape, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Old Town Winter Park?
Select your dates and then use our filters to search for vacation rentals with ac in Old Town Winter Park on Vrbo. With five air-conditioned properties to choose from here, you can look forward to a cool and comfortable break.
How old do you have to be to rent a vacation rental in Old Town Winter Park?
The minimum required age is usually 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your chosen Old Town Winter Park vacation rental before booking your escape.
How long can I rent a vacation rental in Old Town Winter Park for?
The length of time you can book a vacation rental in Old Town Winter Park varies according to the property. Simply enter your preferred travel dates to display a list of options offering extended stays. With many creature comforts like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to get the perfect place to call your home away from home in Old Town Winter Park.
Does Vrbo offer discounts for vacation homes in Old Town Winter Park?
In Old Town Winter Park, you’ll find some fabulous bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re after a weekend getaway or a longer stay, we’ve got plenty of options that’ll suit your style.