Town Of Winter Park Lodging

The Town of Winter Park is located just two miles from Winter Park Resort and is a wonderful choice for families and groups who want to enjoy an equal share of on and off-slope activities during their Winter Park vacation. Offering the largest variety of both uptown and downtown Winter Park lodging options in the area, our Town Of Winter Park vacation rentals range from one bedroom condos to seven bedroom vacation homes.  


Properties Available 43 properties available
Trout Creek Lodge is your group's premier getaway nestled in the mountains of Winter Park. Boasting six large bedrooms, three lounge areas, a high-end kitchen, wrap around panoramic deck, private hot tub (and more!) this home is sure to please everyone in your group.Enter Trout Creek Lodge and take in the thoughtful lay
Hot HOT 44
Private Hot Tub
Valley Views
Trout Creek Lodge
Home
Bedrooms 6 bedroom
Bathrooms 7
Guests 19 guests
Rating 4.9 (141)
Step into Two Brothers Lodge and you'll immediately feel at home amongst the open layout and the fresh and clean updated decor and design. The main level living room boasts an oversized couch and warm gas fireplace that is the perfect place to come together after a fun day adventuring around Winter Park, or relax and watch a movie on
Hot HOT 122
Private Hot Tub
Valley Views
Two Brothers Lodge
Home
Bedrooms 6 bedroom
Bathrooms 4
Guests 19 guests
Rating 4.9 (127)
Welcome to Arrow on the Creek, a new & modern, colorful & eclectic, large five bedroom townhome that's perfectly located just steps from shopping, dining & the fun activities on Vasquez Creek near Hideaway Park. This Arrow townhome is a brand new bookend property that features four levels of modern construction and stylish deco
Hot HOT 38
Private Hot Tub
Downtown
Arrow on the Creek
Townhome
Bedrooms 5 bedroom
Bathrooms 5
Guests 14 guests
Rating 4.8 (47)
Welcome home to Creekside Retreat, a spacious 5-bedroom, 4.5-bathroom home overlooking Vasquez Creek in Winter Park. With room for up to 18 guests, this three-level home is a great fit for families and larger groups looking for plenty of space to spread out while still being close to everything Winter Park has to offer. You can walk to downtown Win
Hot HOT 31
Private Hot Tub
Creekside
Creekside Retreat
Home
Bedrooms 5 bedroom
Bathrooms 4
Guests 18 guests
Welcome home to Dilly Dally Chalet, a spacious 5-bedroom, 3.5-bathroom home in Winter Park’s Roam neighborhood. With room for up to 17 guests, this three-level home offers plenty of space for families and larger groups, with multiple living areas, a private hot tub, chef’s kitchen, dedicated workspace and easy access to downtown Winter
Hot HOT 20
Downtown
Private Hot Tub
Dilly Dally Chalet
Home
Bedrooms 5 bedroom
Bathrooms 3
Guests 17 guests
Imagine pulling into the garage and the kids hopping out of the car to run through the house, exploring all the rooms and treasures inside. It's this excitement that we hope you experience throughout your stay at Eagle Wind Lodge and in Winter Park. Cooks will love the large kitchen with tons of counter space, a wall of windows looking into the
Hot HOT 41
Private Hot Tub
Valley Views
Eagle Wind Lodge
Home
Bedrooms 5 bedroom
Bathrooms 4
Guests 16 guests
Rating 4.9 (138)
Wrap yourself in mountain style at Elk Lodge, a spacious mountain chalet situated in Winter Park, just minutes from world-class golf and skiing that sleeps up to 19 guests. This mountain getaway combines the perfect blend of amenities, spacious layout, and thoughtful design. Featuring high-end finishes and a touch of luxury thro
Hot HOT 23
Private Hot Tub
Elk Lodge
Home
Bedrooms 5 bedroom
Bathrooms 5
Guests 19 guests
Rating 4.9 (114)
Welcome to Alpine Proper, a beautiful four bedroom, six bathroom townhome perfectly located in the heart of downtown Winter Park. Just steps from shopping, dining, the free shuttle, and all the fun activities Winter Park has to offer, this spacious home is the perfect home base for your next mountain getaway.Head up to the main level and you'll
Hot HOT 32
Downtown
Private Hot Tub
Alpine Proper
Townhome
Bedrooms 4 bedroom
Bathrooms 4
Guests 9 guests
Welcome home to Après Chalet, a modern four-bedroom chalet that's perfectly located in the heart of Winter Park, just a short walk from downtown dining, shopping, Hideaway Park and the free shuttle to Winter Park Resort. This spacious home sleeps up to 12 guests and features modern mountain design, a private rooftop patio with a bubbling
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Pet Friendly
Private Hot Tub
Après Chalet
Home Pet Friendly
Bedrooms 4 bedroom
Bathrooms 4
Guests 12 guests
Welcome home to Arrow 264, a modern, colorful & eclectic, large four-bedroom townhome that's perfectly located just steps from shopping, dining & the fun activities at Hideaway Park. This large Arrow townhome features four levels of modern construction, luxury furniture, a huge rooftop patio with an outdoor hot tub that's bubbl
Hot HOT 45
Rooftop Hot Tub
Downtown
Arrow 264
Townhome
Bedrooms 4 bedroom
Bathrooms 3
Guests 8 guests
Rating 4.8 (42)
Gather & Glow is where your Colorado adventure dreams await, right in the heart of Downtown Winter Park! This luxurious four-bedroom mountain townhome combines high-end finishes, thoughtful design, and playful spaces with an unbeatable location just steps from Winter Park's best restaurants, shops, and activities. The main level offers a co
Hot HOT 15
Downtown
Rooftop Hot Tub
Gather & Glow
Home
Bedrooms 4 bedroom
Bathrooms 3.5
Guests 10 guests
Hygge Hideaway is tucked into the hillside of Winter Park's serene Bear Trail neighborhood, offering a cozy mountain escape surrounded by nature. With rustic-chic finishes, warm touches, and plenty of space for your group to relax, this spacious four-bedroom cabin is designed for slowing down and reconnecting. Hygge (noun) | hyoo-guh: a cozy qu
Hot HOT 20
Private Hot Tub
Valley Views
Hygge Hideaway
Home
Bedrooms 4 bedroom
Bathrooms 3.5
Guests 10 guests

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Info About the Town of Winter Park

Located just two miles north of Winter Park Resort, the Town Of Winter Park offers a large variety of shops and restaurants, a bowling alley & movie theater, recreation center and vibrant event scene at the highly acclaimed Rendezvous Event Center at Hideaway Park. Summer visitors enjoy extensive mountain biking and hiking trails, free outdoor yoga and fitness classes, town parks, hot air balloon rides and a lively line-up of music festivals, art fairs and family-friendly events.  Winter activities include sledding at Hideaway Park, cross-country skiing & snowshoeing, plenty of retail therapy, and family fun at Grand Park recreation center.


Downtown Winter Park Lodging

Want to stay in the heart of the action in the Town of Winter Park? The following neighborhoods are within a three minute stroll of the shops and restaurants of the Town of Winter Park.  

Trailhead Lodges Vacation Rentals

The Trailhead Lodges community is a modern, attractive collection of high-end condos, centrally located in the Town Of Winter Park. The #1 spot for music festival lodging, many of the Trailhead Lodges buildings overlook the Rendezvous Event Center at Hideaway Park.   Winter guests love the free sledding hill at Hideaway Park and easy access to the free shuttle service to Winter Park Resort. All of our 1-3 bedroom Trailhead Lodges condo rentals enjoy free access to the complex clubhouse with outdoor pool, hot tub, fire pit and workout room.

Sawmill Station Vacation Rentals

Sawmill Station claims an enviable location in the Town Of Winter Park, just off Hideaway Park and the Rendezvous Event Center, and right by the Fraser River. An easy stroll will find you at your pick of restaurants and the free shuttle service to Winter Park Resort. All of our 3 & 4 bedroom Sawmill Station townhomes offer three levels of living space, plus a private garage and private balcony with gas grill.  

Arrow Townhomes Vacation Rentals

Built in 2018, the attractive Arrow complex sits just off of the main street, within a three minute walk of Hideaway Park and the many retail stores and restaurants at Cooper Creek Square. Built over three levels, our three and four bedroom Arrow vacation rentals feature feature a rooftop patio (many with a private hot tub), a private garage and a modern mountain living design.

Uptown Winter Park Lodging 

Lodging in the Town of Winter Park extends beyond the main downtown area, into many attractive neighborhoods of townhomes and private homes that border National Forest and public spaces.

Bear Crossing Vacation Rentals

Bear Crossing is a newer townhome development, set in a peaceful neighborhood above the Town Of Winter Park.  Ideal for families and small groups, this lovely community of townhomes backs onto hiking and biking trails in the National Forest and enjoy beautiful views of the Continental Divide. All of our Bear Crossing vacation rentals are high-end, 3 bedroom/3 bathroom homes, with either a private hot tub or jetted bathtub, heated one car garage and modern mountain furnishings and decor.

Luxury Homes & Cabins Rentals

Looking for the quintessential Rocky Mountain Retreat?  Look no further.   Our mountain homes offer the perfect base camp for larger groups and families. Ranging from 3-7 bedrooms in size, all of our stand alone homes offer multiple social spaces, luxurious decor and high-end amenities. If you've ever dreamed of taking the family to a big cabin in the woods, or are seeking the perfect executive retreat, our Winter Park luxury vacation homes might be just what you are looking for.