2024 Cyber Monday Lodging Deals

2024 Cyber  Monday Lodging Deals are here!

Book your Winter Park Lodging today for the rest of the 2024-2025 ski season.

Use promo code CM for a 10% discount off 2 nights or more

Use promo code BF for Black Friday deals or SBS for Small Business Saturday

This offer is valid for new reservations only and cannot be combined with any other offers.  All reservations must be made by midnight on 12/2.  Certain nightly minimums may apply.

If you have specific questions or need personalize assistance with your booking, call us at 1-800-215-6535book online or email us at info@staywinterpark.com.


Properties Available 196 properties available
This luxurious Arrow townhome unit is an ideal choice for couples (and Pets!) seeking a relaxing getaway in downtown Winter Park. With 3 bedrooms, it can accommodate up to 10 guests, providing stunning views and a private hot tub for a truly memorable vacation experience.The lower level features a private garage with space for 2 cars parked in tand
Hot HOT 14
Arrow at Winter Park Unit 276
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.7 4
Experience the luxury of this spacious and stunning home that is pet friendly and has so much to offer! Homer’s Hideaway is a newly constructed, 3 bedroom plus loft, 3.5 bath private residence that can comfortably sleep 10 people. Located in the desirable Grand Park neighborhood, it is perfect for a large family or two families vacationing togethe
Hot HOT 11
71 Alder Brook Homer’s Hideaway
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 17
This townhome in Fraser boasts a spacious backyard, perfect for pets, and is ideal for families looking for a rental property. It offers ample space and excellent amenities. Situated conveniently close to downtown Fraser, with its restaurants, breweries and summer hiking and biking trails, residents can easily access all the area has to offer. Add
Hot HOT 14
701B Quail
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.8 25
This exquisitely renovated two bedroom residence serves as an ideal destination for a mountain retreat. It is characterized by its bright and welcoming atmosphere, offering breathtaking mountain views from three private decks. Conveniently situated just minutes from downtown Winter Park and roughly three miles from the Winter Park Resort, the pro
Hot HOT 11
Silverado I Building B Unit 204
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 9
This recently built 5-bedroom corner unit at the Arrow townhome development provides unique amenities such as stunning views from the private hot tub overlooking the Continental Divide and hillside scenery of the Rendezvous Event Center for music festivals in downtown Winter Park, as well as partial views of Winter Park Resort from the spacious roo
Hot HOT 14
Arrow at Winter Park Unit 284
Townhome -
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.6 13
The expansive kitchen features newly installed countertops, wooden cabinetry and modern appliances, complemented by a breakfast bar. The dining area provides additional seating for up to four individuals. In the living room, comfortable sofas create an inviting atmosphere for relaxation, allowing guests to enjoy the flat screen TV, gas fireplace a
Beaver Village Unit #1923R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.7 7
The living room features new furnishings that enhance the recently renovated unit, creating an ideal space for relaxation and enjoyment of the serene atmosphere during your mountain getaway. It includes a gas fireplace, flat screen television, a sofa sleeper and access to the a private deck. Situated on the second floor of the building, the unit o
Beaver Village Unit #0922R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 1
A vintage one-bedroom condominium provides a cozy rental option, featuring a private balcony and situated on the ground floor of the building allowing for convenient access to parking and the complimentary town shuttle service.In the primary living area, unwind by the gas fireplace, enjoy the television equipped with a VCR, and make use of the quee
Hot HOT 15
Hi Country Haus Unit 2501
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.4 7
A first floor unit with 1,200 square feet of living space that offer 2 bedrooms and 2 bathrooms. The open living room with a wood paneled accent wall to compliment the lovely furnishings, gas fireplace, TV, VCR, queen sofa sleeper and no air conditioning.In the center of the main room, the dining area overlooks the private balcony and will seat 6
Timber Run Dogwood Unit 7
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 1
This exceptionally spacious condominium is situated just off Main Street in downtown Winter Park, offering stunning mountain views and convenient access to shops, restaurants, outdoor activities and various events.The Moose Haven, aptly named for its mountain-themed décor, has undergone a comprehensive renovation, making it an exceptional vacation
Snowblaze Condos Building C unit 24
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 43
The attractive furniture in the primary living space provides an excellent area to unwind, appreciate the gas fireplace, flat screen TV and entrance to the secluded patio. A modernized dining space accommodates seating for four individuals.The renovated kitchen features hardwood flooring, granite countertops, stainless steel appliances and wooden c
Hot HOT 19
Beaver Village Unit #0412R
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
The residence accommodates up to 12 guests and boasts a charming cabin ambiance, situated on a secluded, wooded acre with stunning views of the continental divide. It is common to spot deer, elk, and even moose in the area. The property is conveniently located just five miles from the base of Winter Park Ski Resort, two miles from downtown Winter P
Hot HOT 6092
61 Jabberwocky
Private Vacation Home - Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
Rating 4.6 10

Tell us what you're looking for and someone will contact you with available options.

By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.
I agree