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Winter Park Pet Friendly Vacation Rentals

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    Travellers to Winter Park are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    30 Matching Rentals in Winter ParkView all 425 rentals
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    Beautiful Mountain House - Luxury in a Rustic Mountain Setting1 / 27
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    6 Bedrooms, 4 Bathrooms, Sleeps 24 Quick View
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    6 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxation at its best in the Colorado Mountains, with a home that has 6 bedrooms separated into four distinct and private areas. It also has three separate living areas. Enjoy the company of others, but you can always retreat to your own space. We love this house when hosting large groups of...
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    Winter Park, Grand County 80442
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 20
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    Mary Jane Chalet1 / 29
    (3)Average
    6 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 3, 2016
    We all loved our stay at the Chalet! The picture depicting the front doesn't really do it justice. It is very ample inside with comfortable furniture, cute decor and ample...
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    About this property
    Get the real mountain experience staying at the Mary Jane Chalet located just 1.5 miles from downtown Winter Park, Colorado! For a group of friends or for the perfect family getaway this residence sleeps up to 10 people. This property is pet-friendly and has a spacious outside pen for fido! It has...
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    Winter Park, Grand County 80482
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming Log Cabin w/Hot Tub, Deck, Ping Pong,Wifi1 / 30
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Patio
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 11, 2016
    Cabin was nice, perfect for two, we had a minor issue with the shower door but is was corrected the same day.The only thing that bothered me was having to walk down the stairs...
    Reviewed July 20, 2016
    My family and I stayed at Bear Claw Cabin and had a great time! The deck out back was my favorite as it was perfect for an afternoon reading in the sun. The teenagers loved...
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    About this property
    This cozy yet spacious Log Cabin is located right in the town of Winter Park. It sits on the mountain side, and there is a ski shuttle pickup at the end of the driveway! Bear Claw Cabin is fully furnished, cozy and inviting. The wood logs are all original (cabin was built in 1974) and it's very...
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    Winter Park, Grand County 80482
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Trailhead Lodges 3231 / 37
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 29, 2016
    The condo is very nice, new, clean, well equipped with a very lovely view. There are no other structures in sight so from the interior of the condo you feel are in a home alone...
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    About this property
    Be one of the first guests to stay in this brand new building, in one of the most sought after locations in downtown Winter Park. With high-end touches throughout and a unique location that affords a rare wrap around deck and forest views, this well appointed property is the perfect year round...
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Patio
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>Location: Timbers 6-1; Ground floor Bedding Configuration: King in the Master bedroom, Queen in the second bedroom, 2 Twin Bunk beds with a trundle bed in the third bedroom. Amenities in unit: PET-FRIENDLY (non-refundable pet deposit will apply), Free Wi-Fi access,...
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Central Heating
    • Mountain Views
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to beautiful Winter Park in comfort and style when you stay at this 2-bedroom, 2-bathroom vacation rental condo that sleeps up to 7 lucky travelers. You'll be within a 5-minute walk of the complimentary ski shuttle to Winter Park Ski Resort and close to a variety of local shops and...
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We take vacations to pause from everyday life. The most memorable vacations are when everything comes together just right and time becomes obsolete. Selah Vista Lodge provides the perfect setting to forget what's unimportant and live in the moment. Overlooking the town of Winter Park, this six...
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    Winter Park, Grand County 80482
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Lakota Antlers townhome is designed for family fun. Enjoy one of the five flatscreen TVs, theater room, and air hockey table that converts into a ping-pong table. The center level of this tri-level townhome has an open floor plan centered around a 55' flatscreen smart TV and gas fireplace...
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    Winter Park, Grand County 80482
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Luxurious Cabin: Two Master Suites, Hot tub, Views1 / 21
    (2)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 14, 2016
    The home was lovely, very spacious, beautiful bathrooms as part of the 2 master suites. Great, timely communications with the property manager Lacey.
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    About this property
    This warm and cozy house will offer you a perfect combination for small or large groups based on this perfect configuration. The family room will offer you the comfort you would expect in a mountain retreat with large vaulted ceilings, beautiful log finishes, a gas fireplace, a large 3D TV with...
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    Location Information
    Winter Park, Grand County 80442
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Bear Crossing 13901 / 33
    (10)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Bear Crossing townhome is located above downtown Winter Park in a family and pet friendly (for one dog $75 fee) neighborhood that backs right onto hiking and biking trails. Enjoy the private hot tub on the back deck, two decks in front with stunning views of surrounding mountains, a heated...
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    2BR Ground-Floor w/ Granite Kitchen, Pool, & Hot Tub - Shuttle to Slopes1 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 2018
    Great location in downtown Winter Park and great access to local hiking hills. Enjoyed the space. Noisy when upstairs come residents down the stairs.
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    About this property
    Bring the whole family to this vacation rental in the Trailhead Lodge complex, complete with two master bedrooms, two en-suite bathrooms, and a sleeper sofa for seven guests. It is in the heart of downtown Winter Park and just steps from Hideaway Park and Ampitheater, bars, restaurants, shopping,...
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxurious 3 bedroom/3 bathroom + bunk room, sleeps 10, steps from downtown, pet-friendly (for one dog $75 fee), community clubhouse and more! Just built in November 2016, be one of the first guests to stay in this brand new, penthouse property in Building 1 at Trailhead Lodges. With high-end...
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Bear Crossing 7451 / 31
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated above downtown Winter Park in a quiet area, Bear Crossing has everything you need! 3 master suites, 2 living areas, and a game room all spread out on 2 levels. Enjoy mountain views from your private deck! This pet friendly (for one dog $75 fee) Bear Crossing Townhome has everything you...
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    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 11
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This pet friendly (for one dog $75 fee) home has a large central living space, three levels of downtown living with three masters, two private decks and one private hot tub, this sawmill station condo is the perfect vacation destination. The centerpiece of the open floor plan is the 58' flat screen...
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    Winter Park, Grand County 80482
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this newly built condo and the centralized location of downtown Winter Park. Trailhead Lodge 133 is right next to Hideaway Park which is home to a concert venue, kids play park, and skate park. Out the back door, you step right onto the Fraser River and endless trail access for hiking and...
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Downtown Location with a hint of seclusion, the pet friendly Whistlestop 110 has the best of both worlds. The three bedroom townhome is split over three levels with two lounge areas, a vast, fully equipped kitchen, open floor plan and lots of natural light. The main level lounge is situated in...
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    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Mountain Views
    • DVD Player
    • Central Heating
    • Cable/satellite TV
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to a Rocky Mountain paradise when you book this 1-bedroom, 1-bath vacation rental condo in Winter Park, which sleeps 4. Boasting all the comforts of home, access to community amenities and an unbeatable location only minutes from the slopes, this unit is ideal for friends, couples or small...
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Patio
    • Grill
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    • Balcony
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>Location! Location! Location! This one bedroom, one bath unit is ideally situated in Fraser Crossing, just across the street from Winter Park Village, which allows for super easy access to all of the amenities located at the base such as: the Zephyr lift (currently being...
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    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Indoor Pool
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful one bedroom remodel on second floor near plenty of parking. Winter ski resort with free shuttle to ski/boarding area, summer close to mountain biking and the best summer weather in the nation. Hunting season in fall is another popular time. It's cozy and classic, well-appointed remodel...
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that if you check-in/out on a major holiday - the reservation may be subject to a double cleaning fee.* For your next alpine retreat, escape to this spacious 2-bedroom, 2-bathroom Winter Park vacation rental cabin that comfortably sleeps 10. Offering all the necessary comforts of...
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    Winter Park, Grand County 80482
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Mountain Views
    • Balcony
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>Location: Snowshoe House; Ground floor. Bedding Configuration: Queen in the Master bedroom, and Queen bed and a Captain's Bunk (Queen bed on the bottom and Twin bed on the top) in the second bedroom. Amenities in unit: Free Wi-Fi access, flat screen TV, private hot...
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    Winter Park, Grand County 80468
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful Mountain Lodge-Ski, Hike, Bike, Relax..1 / 23
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 19 Quick View
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    • Hot Tub
    • Mountain Views
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Central Heating
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful large custom home nestled on 2.5 acres. Built in 2000 and is in like new condition. This home can easily accommodate up to 3 families with 3 levels, 5 bedrooms and 3 bathrooms. This home has 3 living levels, each having a separate sleeping and bathroom area. In addition to the...
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    Location Information
    Winter Park, Grand County 80446
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 19
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Wi-Fi
    • Grill
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the picturesque Rocky Mountains when you book this updated 1-bedroom, 1-bathroom Winter Park vacation rental condo, which sleeps 4 guests comfortably! This property boasts numerous amenities - both shared and private - and a top-notch setting beside a peaceful mountain stream. Just...
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    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect retreat for an outdoor adventure, this spacious 2BR/1.5BA Winter Park townhome backs onto the vast Arapaho National Forest. The property has a convenient location on the free bus route, and it’s less than a 10-minute drive to downtown for skiing, dining, shopping, and year-round...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Mountain Views
    • Central Heating
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Grill
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the Rocky Mountains when you stay at this 1-bedroom, 1-bathroom vacation rental condo in Winter Park. With the capacity to accommodate 4 guests, this condo will ensure the ultimate outdoor retreat, offering a top-notch setting beside a peaceful mountain stream, just minutes from skiing...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Waterfront
    • Mountain Views
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated in the Hi Country Haus Condominium, this ultimate Winter Park getaway lies just steps from Main Street shops, 1 mile to Hideaway Park, and 4 miles from the slopes and trails of Winter Park Resort. This recently remodeled 3-bedroom, 2-bath vacation rental condo sleeps 8 guests with nearly...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Washer
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk or catch the bus, either way; you'll be just minutes from Winter Park Resort when you stay at this spacious 3-bedroom, 2-bath vacation rental home. The 1,900-square-foot interior accommodates up to 8 guests with a fully equipped kitchen, private hot tub and 2 large decks ideal for cookouts on...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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