See all properties
Entire apartment

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Apartment in Winter Park with a hot tub and a fitness center

Choose dates to view prices

Photo gallery for The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Outdoor dining
Interior
Smart TV, fireplace, stereo
Outdoor dining
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire apartment

2 bedrooms2 bathroomsSleeps 61184 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer

Explore the area

View in a map
Winter Park, CO
  • Place, Winter Park Visitor Center
    ‪3 min walk‬
  • Place, Bella Vita
    ‪5 min walk‬
  • Place, Blue Sky Massage
    ‪7 min walk‬

Room options

About the neighborhood

Winter Park

This apartment places you next to Hideaway Park and Winter Park Visitor Center. The apartment includes a kitchen, a fireplace, and a balcony.
View more Apartments in Winter ParkOpens in a new window

What's nearby

  • Hideaway Park - 1 min walk - 0.1 miles
  • Winter Park Visitor Center - 3 min walk - 0.2 miles
  • Bella Vita - 5 min walk - 0.3 miles
  • Blue Sky Massage - 7 min walk - 0.4 miles
  • Grand Park Community Recreation Center - 16 min walk - 0.9 miles

Getting around

  • Fraser/Winter Park Station - 9 min drive
  • Broomfield, CO (BJC-Rocky Mountain Metropolitan) - 102 min drive

Restaurants

  • ‪Wake N’ Bacon - ‬12 min walk
  • ‪The Noble Buck - ‬10 min walk
  • ‪McDonald's - ‬4 min walk
  • ‪Wendy's - ‬5 min drive
  • ‪Ullr's Tavern - ‬12 min walk

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

In floor radiant heat, fireplace. Three comfortable beds to sleep 6 people. We also supply a Pack and Play crib and High chair.

Our condo is a modern mountain retreat. Modern art in all rooms. High definition Tv's in each room for your enjoyment.

Guests have use of the entire apartment, along with clubhouse pool table and fitness room. Year round heated swimming pool and hot tub also available for guest use.

Roger@innisfreehotels.com
Cell 850-393-0063

Within walking distance to all restaurants, night life, shopping, liquor store and grocery store..
Hideaway Park is right next door and has incredible concert venues almost every weekend throughout the summer season. Sledding in the winter time.
The best restaurants are;
Deno's for Steaks and American food (one block on the left).
The Ditch for Burritos and Awesome Hamburgers (one block on the left).
Hernando's for Pizza and Italian food (four blocks to the right on the main street).
Azteca for Mexican food (six blocks to the right on the main street).

Ski area bus runs every 15 minutes to and from the ski area and is located one block from us.

We are located one block from shopping, dining and nightlife. Directly across the street from Hideaway Park where summer concerts take place and sledding in the winter.
There is a $45.00 one time pet fee. There is no smoking allowed in the condo but smoking is allowed on the balcony.
The apartment is heated and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fireplace, and a sofa bed.

Similar properties

TV, fireplace
Wonderful Fraser 2 bedroom, pet friendly, large yard
  • Kitchen
  • Pet friendly
  • Laundry
  • Outdoor Space
8.8 out of 10, Excellent, 6 reviews
$402 nightly
The price is $447
Feb 8 - Feb 9
Total with taxes and fees
Wonderful Fraser 2 bedroom, pet friendly, large yard

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Ceiling fan
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Things to do

  • Billiards/pool table
  • Gym
  • Heated pool

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Property located in a resort
  • Unit size: 1,184 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • This property welcomes pets
  • Dogs only
  • 2 total pets
  • Restrictions apply
  • For more information, guests can reach out to the property at the number on the booking confirmation
  • Service animals exempt from fees

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Property is also known as

Beautifully Furnished 2 Bedroom 2 Bathroom Condo Heart
Beautifully Furnished 2 Bedroom 2 Bathroom Heart Winter Park
Beautifully Furnished 2 Bedroom 2 Bathroom Heart
Beautifully Furnished 2 Bedroom 2 Bathroom Condo Heart
Beautifully Furnished 2 Bedroom 2 Bathroom Heart Winter Park
Beautifully Furnished 2 Bedroom 2 Bathroom Condo Heart
Beautifully Furnished 2 Bedroom 2 Bathroom Heart Winter Park
Beautifully Furnished 2 Bedroom 2 Bathroom Heart
One Block From all Restaurans Shopping Nightlife
One block from all restaurans shopping nightlife.
One block from all restaurans, shopping and nightlife. Condo

Frequently asked questions

What's there to do around this apartment?

This apartment is located in Winter Park, just steps from Hideaway Park and Bella Vita, and within a short walk of Blue Sky Massage. You'll also find Winter Park Ski Resort and Cozens Ranch House Museum within a short drive.

Is there parking available at this apartment?

No, there isn't parking at this apartment.

Is this apartment adjacent to a casino?

No, this apartment is not connected to a casino.

Is there an indoor pool at this apartment?

No, this apartment doesn't have an indoor pool; however, there is a hot tub.

Is The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park a good place to stay for couples?

Amenities that appeal to couples at this apartment include a fireplace, a kitchen, and a smart TV.

Does The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park have a hot tub?

Yes, this apartment has a spa tub.

Does this apartment provide breakfast?

No, this apartment doesn't offer breakfast.

Does this apartment allow pets to stay for free?

Although dogs can't stay for free, they are welcome at this apartment.

Are there rooms with balconies at The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park?

Yes, every apartment at The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park comes with a balcony.

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 214 out of 225 reviews
Rating 8 - Good. 10 out of 225 reviews
Rating 6 - Okay. 1 out of 225 reviews
Rating 4 - Poor. 0 out of 225 reviews
Rating 2 - Terrible. 0 out of 225 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

Valerie K.

Liked: Cleanliness
The most well appointed VRBO we have stayed in over the last 20 years
Stayed 14 nights in Jan 2026

10/10 Excellent

Doug H.

Liked: Cleanliness
We had a great time, the host is friendly, quick to respond and the place is great! Really clean, exactly as advertised. We will definitely be back. Thanks!
Stayed 2 nights in Jan 2026

10/10 Excellent

Wendy M.

Liked: Cleanliness
Very nice balcony and fireplace. Plenty of space for a family of 4. Close to town, the resort, skiing and tubing!
Stayed 4 nights in Dec 2025

10/10 Excellent

Brian P.

Liked: Cleanliness
The condo was perfect for my family's ski vacation at Winter Park. A Short drive or free shuttle away. Very close to downtown Winter Park's shopping and restaurants. The two bedroom two bath unit had room for everyone and all of our gear. Living room and kitchen felt like it had extra room for a traditional condo as well. Roger was very helpful and quick to communicate. Looking forward to staying with him and his condo again.
Stayed 8 nights in Nov 2025

10/10 Excellent

Cindy R.

Liked: Cleanliness
Very clean home. Host was great. The kitchen was very well equipped and I appreciated the full size washer and dryer that were in the condo.
Stayed 3 nights in Oct 2025

10/10 Excellent

Jim F.

Liked: Cleanliness
Great accommodation! Every thing you needed was there!
Stayed 3 nights in Sep 2025

10/10 Excellent

alan P.

Liked: Cleanliness
Stayed 3 nights in Aug 2025

10/10 Excellent

Cynthia W.

Liked: Cleanliness
Roger’s spacious, well-maintained condo was extremely clean and smelled great. It had lovely decor and was very thoughtfully stocked with everything you would need during your stay: spices and cooking ingredients, utensils, pots and pans, paper towels, bathroom supplies, towels for the pool and hot tub, dog bowls, dishwasher and laundry pods and much more. Roger was very responsive and helpful. The location is perfect for walking to restaurants, coffee shops, entertainment, a park, and stores, with easy and close access to hiking trails and the ski resort. We had a wonderful stay with our 2 dogs and hope to book his condo again when we return to WP.
Stayed 9 nights in Aug 2025

10/10 Excellent

Christy C.

Liked: Cleanliness
The condo at Trailhead is fantastic! The inside is exactly as pictured and very clean. The hot tub & heated pool are only steps away. It's right behind the park & very convenient to walk to bars & restaurants in the town. Highly recommend as a place to stay!
Stayed 4 nights in Aug 2025

10/10 Excellent

Macaela S.

Liked: Cleanliness
Everything was great! Well equipped condo walking to distance to so many things! So many things for kids to do in the area as well as adults! The host was very helpful! Would definitely stay again.
Stayed 5 nights in Aug 2025

10/10 Excellent

Jason S.

Liked: Cleanliness
Great property in the best location. Right in the heart of Downtown Winter Park.
Stayed 4 nights in Aug 2025

10/10 Excellent

Willie S.

Liked: Cleanliness
The stay was perfect, Roger was transparent with communication. The unit was very clean, kitchen was perfectly organized a definite 5 stars and will recommend to anyone staying at winter park
Stayed 3 nights in Jul 2025

10/10 Excellent

Allison P.

Liked: Cleanliness

Winter Park

A lovely condo that is clean, well appointed, and comfy. It was better than described, and Roger was a great host. I’d recommend 10/10!
Stayed 3 nights in Jul 2025

10/10 Excellent

Drew C.

Liked: Cleanliness
Great place
Stayed 3 nights in Jul 2025

10/10 Excellent

Shelly C.

Liked: Cleanliness

Condo was great!

The condo was in geat condition, very clean, well stocked and perfect location. The communication with our host, Roger, was timely and helpful. We would definitely stay here again.
Stayed 2 nights in Jun 2025

10/10 Excellent

Catherine W.

Liked: Cleanliness

Three day getaway in Winter Park

We enjoyed staying at this property recently. It was clean, quiet, spacious, comfortable and in a great location. Everything we needed was there. We would choose this spot again. Thank you so much.
Stayed 3 nights in Jun 2025

10/10 Excellent

Andrea H.

Liked: Cleanliness

Beautiful condo in a perfect location

My husband and I stayed in Winter Park with our two dogs and absolutely loved our time. Check in was easy, the apartment was more spacious than we expected, and Roger was very communicative and helpful. The condo was very clean, cute, and well-stocked with everything you could need. Beds were comfortable. Walking distance to restaurants. We especially enjoyed sitting out on the deck on crisp evenings. We will absolutely be back!
Stayed 4 nights in Jun 2025

10/10 Excellent

Courtney H.

Liked: Cleanliness

Close to town

Loved walking from the Condo into town for dinners. Enjoyed the hot tub most nights. The pool was too cold for me but saw plenty of kids swimming in it. The condo had a well appointed kitchen. It was perfect for the two of us. The second bedroom seemed small for two adults and the second bathroom was not very private overall. Luckily the one by the entrance allows for more privacy. Overall a wonderful experience. Roger was excellent at communicating.
Stayed 8 nights in Apr 2025

10/10 Excellent

Jessica R.

Liked: Cleanliness

Great place

The place was a great place and great location
Stayed 3 nights in Apr 2025

10/10 Excellent

Anna P.

Liked: Cleanliness

Spring skiing family getaway

Clean and cozy condo in a nice location!
Stayed 2 nights in Apr 2025

10/10 Excellent

Ashlea M.

Liked: Cleanliness

Great stay for family ski with pets

Plenty of space for 2 adults 2 kids 2 pets. Very well stocked with kitchen essentials and other fun items like games and dog bowls and mats. The host was great and responsive. We loved being able to walk to the playground and sled hill that is just steps away. For skiing we opted not to use the free Lift shuttle, though it did look convenient. Instead we parked in free lot G at winter park and used the free shuttle from there to the Gondola.
Stayed 5 nights in Mar 2025

10/10 Excellent

Lauran T., Springfield VA

Liked: Cleanliness

Race Weekend Getaway

We travel all over the mountains for ski races and stay in many different types of lodging. This location was wonderful, easy to access and the amenities were wonderful. We will for sure join you again!
Stayed 2 nights in Mar 2025

10/10 Excellent

Nate F., Ballwin, MO, USA

Liked: Cleanliness

Great as Always

This is our second stay at Roger’s place. The condo is as described, has everything you need (well stocked kitchen, grill, laundry, etc.), and is close to restaurants and the shuttle. Roger is a great host and is very responsive. We always try to book Roger’s place when we are in WP.
Stayed 6 nights in Mar 2025

10/10 Excellent

Robin H., Longview

Liked: Cleanliness

Great spot

Awesome location great condo- condo was extremely well stocked had everything we needed and Roger was qick ro ŕ
Stayed 3 nights in Mar 2025

10/10 Excellent

amelia b.

Liked: Cleanliness

very comfortable

love the shuttle busses! never moved the car!
Stayed 3 nights in Feb 2025

Hotels