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Pet Friendly Holiday Rentals in Winter Park

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    Travellers to Winter Park are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    $511
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    1 / 8
    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 4
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    $267
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    1 / 29
    5 of 5 stars (9) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 10
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    $167
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    4.5 of 5 stars (38) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    $243
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    1 / 28
    4.5 of 5 stars (27) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    **Summer Special** Save 20% on our summer stay if you book by April 30th, 2015. 3 Night minimum stay required. A modern and spacious retreat for family and friends, including your favorite furry friend, Trademark #70 is a pet-friendly town house located just 1/3 mile from the Winter Park Resort ski... View all property information
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    Location Information
    Winter Park, Grand County 80482
    5 of 5 stars Reviewed 10 August 2014
    This place was perfect for us - family with 4 young kids and a dog. It's walking distance to the mountain and the kids loved all the activities there (mt slide, bungee/trampoline...
    4 of 5 stars Reviewed 5 March 2014
    We enjoyed the place for the week-end and it made such a difference to be able to bring the family dog. Our kids ski, we snowshoe and the proximity of each of these was...
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    1 / 22
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 14
    travellers have booked this property
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    This beautiful mountain home is centrally located in the Fraser Valley. It is luxury in a rustic mountain setting. The home is situated on a large wooded lot giving you the peace and tranquility you are looking for in a mountain getaway. Yet, the home is just minutes away from world class downhill... View all property information
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    Winter Park, Grand County 80442
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    1 / 9
    4.5 of 5 stars (35) Very good
    Studio / 1 Bathroom / Sleeps 4
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    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    **Summer Special** Save 20% on our summer stay if you book by April 30th, 2015. 3 Night minimum stay required. Property Description: This quaint, yet spacious, studio is perfect for a small family, couple or a few friends wanting to be on the doorstep of the restaurants, shops & slopes of Winter... View all property information
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    Location Information
    Winter Park, Grand County 80482
    5 of 5 stars Reviewed 10 July 2014
    Loved the smell of pine trees through the open window. Questions we had were acted on very promptly.
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    $254
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    1 / 19
    4.5 of 5 stars (21) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    **Summer Special** Save 20% on our summer stay if you book by April 30th, 2015. 3 Night minimum stay required. Property Description: This exceptional Village condo is one of a kind, situated in the corner of the building and overlooking the Village and Ice Skating Pond. It has its own 120... View all property information
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    Location Information
    Winter Park, Grand County 80482
    5 of 5 stars Reviewed 13 July 2014
    Fabulous place for our family of four and two dogs. Plenty of space, great patio, wonderful views. We had a very relaxing stay and would choose this place again. Our favorite...
    4 of 5 stars Reviewed 23 October 2012
    Very comfortable two bedroom condo that slept our family of seven comfortably. Patio had a great view of slopes and village. Garage parking a plus in the winter. Hot tub outside...
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    $216
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    1 / 30
    4 of 5 stars (5) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    NOW THRU 11/26/2014- STAY 3 NIGHTS, GET THE 4th FREE!! (Valid for stays during 10/15/2014 thru 11/26/2014 only. Pricing will be adjusted upon booking.) This fully equipped log cabin in the town of Winter Park sleeps 6 and is right on the shuttle route. (Shuttle stops at end of driveway.) It offers... View all property information
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    Location Information
    Winter Park, Grand County 80482
    4 of 5 stars Reviewed 12 August 2014
    Bear Claw Cabin was what we expected based on pictures and information provided. We loved the true cabin feel and the hot tub and deck. The cabin had everything we needed. The...
    4 of 5 stars Reviewed 30 June 2014
    My family of 4 stayed here for 3 nights. There are two bedrooms, one bath. One bedroom has a full sized bed and two twins, the other has a full sized bed. With two teenagers we...
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    1 / 17
    4.5 of 5 stars (37) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (37) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    **Summer Special** Save 20% on our summer stay if you book by April 30th, 2015. 3 Night minimum stay required. Click Here For Interactive Floor Plan With PhotosProperty Description: With all-new, plush furniture and bedding, plus a full kitchen, this beautiful condo at the base of Winter Park... View all property information
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    Location Information
    Winter Park, Grand County 80482
    5 of 5 stars Reviewed 12 July 2014
    We stayed in a different unit in this complex last year and loved it, so when shopping for a good deal, we were ecstatic to discover Winter Park Lodging Company's rates were more...
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    $318
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    1 / 23
    3.5 of 5 stars (5) Average
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Come enjoy a beautiful home nestled in the aspens surrounded by open space. Pine Cone Cabin is a 5 bedroom, 3 bath home that can comfortably accommodate 10 people in 3,100 square feet of space with a 2 car garage and a large sunny deck to enjoy the scenery. The upper level has a Master bedroom with... View all property information
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    Location Information
    Winter Park, Grand County 80446
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    $637
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    1 / 25
    3.5 of 5 stars (16) Average
    9 Bedrooms / 9 Bathrooms / Sleeps 30
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Ski in...Shuttle out at this Winter Park, Colorado rental home. A 9 bedroom home that sleeps 30. With over 5,000 square feet, this private home located in Old Town Winter Park has character and atmosphere. Formerly a Bed and Breakfast, this 9 bedroom, 9 bath home has been converted to a private... View all property information
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    Location Information
    Winter Park, Grand County 80482
    5 of 5 stars Reviewed 19 February 2014
    After reading a few of the other reviews I was a little worried about the house but upon arrival I can say that I was extremely pleased with Pines Inn property. The house was...
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    $140
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    1 / 7
    4 of 5 stars (7) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    We only need three words to describe our small, but perfect retreat… 1. LOCATION! 2. LOCATION! 3. LOCATION! You’ve just found the perfect place to escape to in Winter Park. Aside from the beauty of the mountains and the unbelievable skiing, the town of Winter Park centers around a fun... View all property information
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    Location Information
    Winter Park, Grand County 80482
    5 of 5 stars Reviewed 29 December 2014
    This little cottage was so perfect for my husband and I. It's super cozy. Has everything you need. The owners are very nice. The satellite went out, so no TV for the first night...
    4 of 5 stars Reviewed 4 December 2014
    Clean, no frills cabin centrally located in downtown Winter Park. Perfect for a couple looking for a place to crash on a mountain getaway.
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    $114
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    1 / 13
    1 of 5 stars (1) Terrible
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Fireplace
    • Grill
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This 2 story vacation rental town home is located in Hide-A-Way Village, above downtown Winter Park, Colorado. This town home is adjacent to the Fraser River and surrounded by a pine forest. The home has two bedrooms, 1.5 bathrooms- and can sleep up to seven. This is a pet friendly unit. The lower... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $345
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    1 / 28
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    **Summer Special** Save 20% on our summer stay if you book by April 30th, 2015. 3 Night minimum stay required. Property Description: What a majestic setting! This private 2,745 square-foot home is situated above downtown Winter Park with gorgeous views of the Continental Divide and surrounding... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $267
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    1 / 20
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    **Summer Special** Save 20% on our summer stay if you book by April 30th, 2015. 3 Night minimum stay required. Property Description: Located above downtown Winter Park, the Bear Crossing Townhome has everything you want for an unforgettable mountain getaway. Boasting two living areas, this townhome... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $331
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    1 / 22
    4 Bedrooms / 3 Bathrooms / Sleeps 14
    traveller have booked this property
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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... View all property information
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    Location Information
    Winter Park, Grand County 80442
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    $292
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    1 / 16
    6 Bedrooms / 3 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Get the real mountain experience staying at the Mary Jane Chalet located on Forest Trail, 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 14 people. This property is pet friendly and has a spacious outside pen... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $255
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    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 9
    traveller have booked this property
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    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Welcome to Slopeside #203, the perfect all-season get-a-way. Located in the highly desirable ski base community of Slopeside Village, our luxury 4 bedroom, 3 full bath townhome condo is within walking distance of the resort, the ski lifts and the Fraser River Trail. The free resort ski shuttle... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $395
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    1 / 22
    6 Bedrooms / 4 Bathrooms / Sleeps 20
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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... View all property information
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    Location Information
    Winter Park, Grand County 80442
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    $395
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    6 Bedrooms / 4 Bathrooms / Sleeps 24
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Perfect setting in the Colorado Mountains, with a home that has 8 sleeping areas (5 dedicated bedrooms, private game room has futon and queen air mattress available, living room and family room both have a sleeper sofa). The game room also includes a ping pong table! Enjoy the company of others,... View all property information
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    Location Information
    Winter Park, Grand County 80442
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    $172
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Nicely updated two bedroom two bathroom Winter Park condo located in the downtown area and minutes from Winter Park Resort. Visitors will enjoy the mountain themed condo with wood furnishings and warm touches throughout. Condo is ideal for families, singles or couples looking for a mountain... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $147
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    1 / 15
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Balcony
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Basic two bedroom one bathroom condominium in cul de sac 15 - 20. Full kitchen, living room and dining room with queen bed in master bathroom Extra bedding with queen sofa sleeper in living room. On free shuttle route to Winter Park Resort and easy walking distance to town.'NO PETS ALLOWED.... View all property information
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    Location Information
    Winter Park, Grand County
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    1 / 13
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Whether you are traveling for a weekend or a longer period of time, this two-bedroom condo is a great base for exploring town and hitting the ski slopes. Just minutes from the Winter Park Ski Resort and town, this vacation home is sure to please. The suite is situated on the second floor of... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $147
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    1 / 10
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Make the most of your Winter Park getaway by renting this one-bedroom condo located on the second floor of building 16. Winter Park Ski Resort is just a shuttle ride away, and town is within walking distance. There are plenty of spots to relax inside this lovely abode, including the living... View all property information
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    Location Information
    Winter Park, Grand County 80482
    5 of 5 stars Reviewed 16 December 2014
    Condo was very nice for our family ski weekend. Unit was updated and had exactly what we needed for 2 great days of Winterpark skiing. Only complaint is the distance to the hot...
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    1 / 13
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    If you're seeking fun and relaxation during your upcoming Winter Park stay, you might want to rent this one-bedroom unit. It is close to skiing and town, and situated in an amenity-laden condo resort. Beaver Village Condominiums offers guests use of its heated indoor pool, sauna, hot tubs, and... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $172
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    After a challenging day on the slopes, return to your condo resort's clubhouse and relax your weary muscles in the hot tub or heated indoor pool. A sauna is also provided for supreme tranquility. This unit is situated on the third floor of building 20, close to skiing, shops and restaurants. At... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $172
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    1 / 11
    4 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    For an unforgettable mountain getaway, consider renting this two-bedroom condo just minutes from skiing, shops and restaurants. It's bursting with excellent amenities, including a gas fireplace, full kitchen, and wireless Internet. Show off your barbecuing skills with the grill on the deck. Your... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $147
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    1 / 10
    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    If you're in a need of a vacation rental for your next trip to Winter Park, think about staying here. Not only is this two-bedroom unit tucked away in a beautiful setting, but it's close to skiing and town. Perfect for two couples, this second-floor suite has a queen bed in the master bedroom and... View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $223
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    1 / 14
    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy the incredible views of Winter Park Resort and Mary Jane from this three bedroom, two and a half bath town-home located in the beautiful Lakota subdivision - Built in 2005, this three story town home has all you need for a family ski trip or summer vacation. After a day of adventure skiing at... View all property information
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    Location Information
    Winter Park, Grand County 80482
    From
    $147
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    1 / 11
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Building 6, 1st floor, queen in master bedroom, sofa sleeper in living area, located in circle 5-9. View all property information
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    Location Information
    Winter Park, Grand County 80482
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    $172
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    1 / 13
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Building 6, 1st floor, queen in master bedroom, 2 twins in second bedroom, sofa sleeper in living area. Located circle 5-9. View all property information
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    Location Information
    Winter Park, Grand County 80482