See all properties
Entire apartment·Private host

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Choose dates to view prices

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

Outdoor dining
Outdoor dining
Fridge, microwave, oven, stovetop
Interior
Interior

Reviews

10 out of 10
Exceptional

Entire apartment

2 bedrooms2 bathroomsSleeps 6110 sq m

Popular amenities

  • Hot tub
  • Parking available
  • Pet-friendly
  • Dryer
  • Pool
  • Gym

Explore the area

View in a map
Winter Park, CO
  • Winter Park Visitor Center
    ‪3 min walk‬
  • Trestle Bike Park
    ‪5 min drive‬
  • Winter Park Ski Resort
    ‪6 min drive‬

Room options

Similar properties

Terrace/patio

NEW pet friendly 1 bedroom - great location and amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
4.9 out of 5, Exceptional, 16 reviews
The price is €204
includes taxes & fees
19 Sept - 20 Sept
NEW pet friendly 1 bedroom - great location and amenities

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.
Our customers tell us they can't get enough of this apartment's great location. During your stay, you're just a quick walk from Hideaway Park. Enjoy features like a gym, a hot tub, and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the apartment.
  • The apartment offers a kitchen, a washing machine, and 2 bathrooms
  • Free WiFi (speed: 250+ Mbps (good for 3–5 people or up to 10 devices))
  • Amenities include laundry facilities and an elevator
  • Onsite recreation includes a gym
  • Steps from Hideaway Park and Winter Park Visitor Center
This apartment offers its guests a hot tub and a fitness center. This apartment also features barbecue grills, laundry facilities, and an elevator.

This Winter Park apartment is smoke free.

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Hot tub

Internet

  • Available in the apartment: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

  • Lift
  • Smoke-free property

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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 pets
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

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

Reviews

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

10

Exceptional

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

8.0/10

Eco-friendliness
Rating 10 - Excellent. 207 out of 218 reviews
Rating 8 - Good. 10 out of 218 reviews
Rating 6 - Okay. 1 out of 218 reviews
Rating 4 - Poor. 0 out of 218 reviews
Rating 2 - Terrible. 0 out of 218 reviews

Reviews

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

10/10 Excellent

Graham H.

Liked: Cleanliness

Well stocked and supplied.

Very clean, clear and responsive communication from the owner. Condo was stocked with everything we needed for Presidents' day weekend, even with birthday candles to help celebrate our friend's birthday! The floors we heated also, and the included ski locker came in clutch for our stay. Loved every aspect of the visit, and would love to come back again.
Stayed 3 nights in Feb 2025

10/10 Excellent

Shawn H.

Liked: Cleanliness

Excellent location

Excellent location for skiing and entertainment. Located right off of the main drive with plenty of parking. Outdoor hottub and heated pool were a bonus.
Stayed 4 nights in Jan 2025

10/10 Excellent

Debra F.

Liked: Cleanliness

Beautiful, well appointed property!

This condo is in terrific condition with a well appointed kitchen. The heated flooring was great and easy to maintain. For our purposes, it was in a handy location and we enjoyed the well-groomed trail adjacent to the property. We would definitely book this property again!
Stayed 2 nights in Jan 2025

10/10 Excellent

Steven N.

Liked: Cleanliness

Condo

Condo is very clean and modern. Very comfortable beds and easy access to hot tub across the street. Walking distance to great restaurants. Highly recommend staying here. We will be back .!
Stayed 2 nights in Jan 2025

8/10 Good

Laurie B.

Liked: Cleanliness

Great location wrt river & river ski/dog walk trail but noisy!

This Trailhead condo is in a great outdoor location - also spacious for two people, very suitable for dog, clean & nice. It was quiet & peaceful Mon-Thurs afternoon but as the weekend crowds rolled in, the traffic on the external metal stairs (elevator was broken) became extremely loud & renters in unit above (this is a 2nd floor unit in three-floor building) made sleep & relaxing pretty tough. Great if you can be there mid-week.
Stayed 4 nights in Jan 2025

10/10 Excellent

Allison H.

Liked: Cleanliness

Great accommodations and location

The condo had everything we needed to feel right at home. After a long day of skiing it was great to come back and relax. The location made it easy to hop on bus lines and access restaurants and groceries. Everything was in a short walking distance. The nearby park was also a bonus for our kids.
Stayed 4 nights in Dec 2024

10/10 Excellent

Matt w.

Liked: Cleanliness

Great spot

Stayed here with my friend and his 13 year old for a couple days of skiing. It's a great place and close to town/winter park shuttle. Nice hot tub and pool area as well. I would definitely stay here again.
Stayed 2 nights in Jan 2025