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Pet Friendly Holiday Rentals in Winter Park

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    $193 Average
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    Travellers to Winter Park are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in Winter ParkView all 392 rentals
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    Ski In/Out Resort Village #4646 - Free Activities/No Deposit/Resort Discounts1 / 24
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Ski In/Out Resort Village #4475 - Free Activities/Resort Discounts/Great Views1 / 24
    (37)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Ski In/Out Resort Village #3313 - Free Activities/Resort Discounts/Great Views1 / 24
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Ski In/Out Resort Village #3301 - Free Activities/Resort Discounts/Great Views1 / 24
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Central Heating
    • Housekeeping Included
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Shared Indoor Pool
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We had a wonderful stay at Frazier Crossing. The accommodations were fabulous! The condo was exceptionally clean and well appointed. We had absolutely everything we needed. The...
    Reviewed 19 July 2017
    In Winter Park for the 35th Winter Park Jazz Festival. Had a great time. Stayed at Fraser Crossing - 2 Bedroom Condo 3rd floor. Unit was beautifully decorated - clean...
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ski In/Out Resort Village #4474 - Free Activities/Resort Discounts/Great Views1 / 24
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • Housekeeping Included
    • Mountain Views
    • Wi-Fi
    • Sauna
    • Satellite TV
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    My sister, niece, and I enjoyed our time in Winter Park immensely. The condo's location was perfect to enjoy hiking and activities at the resort. The hot tub was amazing!
    Reviewed 6 June 2017
    We have had a lovely stay in this lovely 2bedroom with patron condo. Would definitely return and might have to permanently move here!
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ski In/Out Resort Village #3133 - Free Activities/Resort Discounts/Great Views1 / 24
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Sauna
    • Shared Indoor Pool
    • Mountain Views
    • Satellite TV
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    Great place to stay during the summer for the Winter Park Jazz festival, location to the base of the mountain. This is a little distance from Hideaway Park, but transportation...
    Reviewed 30 June 2017
    Our condo at Winter Park Village was awesome. It had everything we needed for our stay. Would definitely come back again.
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ski In/Out Resort Village #3129 - Free Activities/Resort Discounts/Great Views1 / 24
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Indoor Pool
    • Housekeeping Included
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Sauna
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Our family of 6 had a great time in Winter Park staying at this condo. It was across the street from all the action of the resort. Logan was helpful on the day of check in.
    Reviewed 2 weeks ago
    Everything at winter park was awesome! The condo was beautiful and clean, the amenities were great, and the area was outstanding! We would love to come back and stay again!
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    About this property
    Have the quintessential Rocky Mountain experience when you stay at this amazing ski-in/ski-out Winter Park Resort vacation rental. Outfitted with all the modern comforts of home, this marvelous unit is perfect for your Colorado mountain retreat. The newly built luxury 2 bedroom/2 bath condo sleeps...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Mountain Cottage1 / 7
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2016
    What a wonderful little cabin! Truly a block from the center of town. Everything we needed was in the cabin, really perfect for the two of us. We only had two problems staying...
    Reviewed 29 December 2015
    Just what you need for a weekend of skiing and exploring the town. Right on the shuttle route with access to all the town has to offer, this is the place to get. Cozy and...
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    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...
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    Location Information
    Winter Park, Grand County 80482
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Charming Log Cabin w/Hot Tub, Deck, Ping Pong,Wifi1 / 30
    (11)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Patio
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 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 20 July 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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    Location Information
    Winter Park, Grand County 80482
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Pines1 / 16
    (16)Average
    9 Bedrooms, 9 Bathrooms, Sleeps 30 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 30
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    Fraser Crossing 33261 / 28
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Fraser Crossing is a 'corner' unit with a good sized porch overlooking Winter Park. We loved watching the slackliners, hearing the music and other festivities over the Labor Day...
    Reviewed 22 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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    About this property
    This peaceful corner unit condo overlooks the Village and ice skating pond- with a private 659-square foot balcony with outdoor furniture, perfect for people-watching. A perfect relaxation spot after an action-packed day, and you're only a short walk to restaurants and activities if you'd rather...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Fraser Crossing 34181 / 21
    (35)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ↵This charming studio has everything you need to regroup after a full day. A complete kitchenette for dinner at home, a gas fireplace, and a private ski locker make for an amazingly convenient getaway. Enjoy access to the amenity deck with oversized hot tub, outdoor fireplace, and barbecues- all...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    Mary Jane Chalet1 / 24
    (3)Average
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 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 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...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    Bear Crossing 13901 / 27
    (10)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Satellite TV
    • Hot Tub
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located above downtown Winter Park, the Bear Crossing Townhome has breathtaking views of the Rocky Mountains. You will never want to leave the incredible comfort that this townhome has to offer: brand new private hot tub on the back deck, two decks in front with stunning views of the Resort and...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Amenities & Details
    • Hot Tub
    • Mountain Views
    • Patio
    • 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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    Trailhead Lodges 3231 / 29
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 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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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Bear Crossing 7451 / 30
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located above downtown Winter Park in a quiet residential area, this pet friendly Bear Crossing Townhome has everything you want in your Rocky Mountain retreat. With three master suites, two separate living areas, and a game room spread out on two levels, this property is ideal for groups wanting...
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    Location Information
    Winter Park, Grand County 80482
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 11
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Waterfront
    • Mountain Views
    • Satellite TV
    • Hot Tub
    • Internet Access
    • Central Heating
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to beautiful Winter Park in comfort when you stay at this cozy 2-bedroom, 2-bathroom condo that sleeps 7, right across the street from world-class ski slopes! Situated only a short walk from Winter Park Ski Resort, this condo is perfect for friends, families, and couples seeking a ski and...
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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Waterfront
    • Central Heating
    • Patio
    • Grill
    • DVD Player
    • Satellite TV
    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-bath Winter Park vacation rental cabin that comfortably sleeps 10. Offering all the necessary comforts of home,...
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    Location Information
    Winter Park, Grand County 80482
    Cabin Holiday Rental - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Outdoor Pool (Heated)
    • Central Heating
    • Mountain Views
    • Internet Access
    • Waterfront
    • Hot Tub
    • Satellite TV
    • DVD Player
    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 3. 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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    Location Information
    Winter Park, Grand County 80482
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Mountain Views
    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Indoor Pool
    • Wi-Fi
    • 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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