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2026-11-14
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Hotels in Pioneer Express Winter Park area of Winter Park

Trailside Mountain Retreat With Private Hot Tub

395 Arapahoe Road Winter Park, Co 80482, Winter Park, United States Show map

Offering access to entertainment venues such as Winter Park Resort, situated nearly a 10-minute drive away, the 4-bedroom Trailside Mountain Retreat With Private Hot Tub Villa Winter Park can host up… More

From US$ 592 Book Now

Viking Alpine Haven

62 E Viking Dr #C202, Winter Park, United States Show map

The spacious 3-bedroom Viking Alpine Haven Apartment Winter Park is located 4.7 km from Eagle Wind and around 10 minutes' drive from Looking Glass. This 118 m² apartment capacity is based on up to 10… More

From US$ 342 Book Now

Downtown Wp Timber Top Home I Hot Tub I Views I Game Room I Bunks I Discounted Attractions

29 Timber Circle, Winter Park, United States Show map

Offering a Jacuzzi for a relaxing experience, Timber Top Villa: Luxury Retreat with Hot Tub and Stunning Views Winter Park is located 4 km from Coca Cola Tubing Hill At Winter Park. Providing guests… More

From US$ 732 Book Now

53 East Viking Drive

53 East Viking Drive, Winter Park, United States Show map

During the stay at the 3-bedroom 53 East Viking Drive Villa Winter Park, guests can indulge in snow skiing, hiking, and fisheries or visit the outdoor sports store "Colorado Adventure Park", located… More

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'The Mountain Chalet' - Free Ski Shuttle To Lifts!

900 Vasquez Rd Unit 3, Winter Park, United States Show map

Offering a location 4.8 km from Eagle Wind, 'The Mountain Chalet' - Free Ski Shuttle To Lifts! Winter Park gives access to various tourist spots in the area. More

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Hideaway Village Lenado 4

900 Vasquez Road #4, Winter Park, United States Show map

The 2-bedroom Hideaway Village Lenado 4 Winter Park villa offers proximity to nearby tourist spots, such as Cooper Creek Square, situated a mere 1.3 km away. The accommodation hosts up to 6 guests… More

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New Creek Side Chateau Guest Suite! Booking For Ski Season Now! With Hot Tub!

39 Alpine Way, Winter Park, United States Show map

Located 4.2 km from Safeway, New Creek Side Chateau Guest Suite! Booking For Ski Season Now! With Hot Tub! Winter Park villa gives access to various tourist sites in the vicinity. With a maximum… More

From US$ 673 Book Now

Luxury 4 Bedroom Cabin: 2 King Suites On Shuttle Route

Winter Park, Co, 80452, Winter Park, United States Show map

Situated about 10 minutes by car from Cozens Ranch House Museum, Luxury 4 Bedroom Cabin: 2 King Suites On Shuttle Route Winter Park offers guests to enjoy playground and a dining table. Featuring a… More

From US$ 704 Book Now

1 Mi To Main St! Winter Park Gem W/ On-Site Hiking

96 Hideaway Dr Unit 6, Winter Park, United States Show map

Situated about a 10-minute drive from Winter Park Resort, the 2-bedroom 1 Mi To Main St! Winter Park Gem W/ On-Site Hiking Villa offers guests to enjoy a terrace, a patio, and a dining table. This… More

From US$ 167 Book Now

Winter Park Condo With Fireplace And Mountain Views

100 Hideaway Dr, Winter Park, Co 80482, Usa, Winter Park, United States Show map

To enjoy your vacation in Winter Park, stay at the 50 m² Winter Park Condo With Fireplace And Mountain Views, which is about 10 minutes' drive from Prospector Express and 3.8 km from Main Street. More

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Winter Park Ski Haus

148 Fir Drive, Winter Park, United States Show map

Featuring balloon tours to make your visit more entertaining, the 6-bedroom Winter Park Ski Haus is in the immediate vicinity of Endeavour Lift. Guests can enjoy snow skiing, hiking, and billiard at… More

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Mountain View Retreat, Walk To Winter Park Gondola

Winter Park, United States Show map

Offering a hot tub, the 3-bedroom Mountain View Retreat, Walk To Winter Park Gondola Villa is located around a 10-minute walk from Prospector Express. Suitable for up to 8 guests, this property… More

From US$ 985 Book Now

Slopeside Chalet 113D I Hot Tub I Great Views I Activity Program

113 D Clover Lane, Winter Park, United States Show map

The 2-bedroom Slopeside Luxury Chalet: Mountain Views & Hot Tub Retreat Winter Park, located just around the corner from Endeavour Lift, can host up to 8 guests. Offering a Jacuzzi, the Winter Park… More

From US$ 445 Book Now

Slopeside Chalet 97A I Hot Tub I Great Views I Bunk Room I Work Space I Discounted Attractions

97 Clover Ln #A, Winter Park, United States Show map

Boasting a hot tub, the 2-bedroom Luxury Slopeside Condo: Ski-In/Ski-Out with Hot Tub & Activity Perks Winter Park villa is located about a 10-minute walk from Main Street and can accommodate 8… More

From US$ 395 Book Now

Slopeside Sanctuary - Penthouse < 1 Mi To Lifts!

97 Kinney Way Unit C, Winter Park, United States Show map

Featuring a hot tub, the 3-bedroom Slopeside Sanctuary - Penthouse 1 Mi To Lifts! Villa Winter Park is located around 10 minutes' walk from Main Street and can host up to 12 guests. Providing guests… More

From US$ 1295 Book Now

Zephyr Mountain Lodge Unit 1407

401 Nystrom Ln #1407, Winter Park, United States Show map

The spacious Zephyr Mountain Lodge Unit 1407 Winter Park is located a 6-minute walk from Endeavour Lift and looks out onto the mountain. 3.2 km from Cabriolet, the apartment welcomes guests with spa… More

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Zephyr Mountain Lodge Unit 1306

401 Nystrom Ln #1306, Winter Park, United States Show map

The 50 m² Zephyr Mountain Lodge Unit 1306 Winter Park offers easy access to such tourist sites as Alpine Slide, located about 5 minutes' walk away. Boasting a Jacuzzi, this 1-bedroom apartment… More

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Creekside Unit 403

145 Arapahoe Road #403, Winter Park, United States Show map

Creekside Unit 403 Apartment Winter Park is located about 3 km from Discovery and 10 minutes by car from Winter Park Resort. The maximum occupancy at this spacious 118 m² apartment is 7 guests. More

From US$ 463 Book Now

Hideaway Village Alpine 4

155 Van Anderson Dr., Winter Park, United States Show map

Staying at the 2-bedroom Hideaway Village Alpine 4 Winter Park villa, guests can easily reach Endeavour Lift, located about a 10-minute drive away. Guests can enjoy snow skiing, hiking, and fisheries… More

From US$ 249 Book Now

Cozy Condo On Vasquez Creek W/ Free Shuttle Access

145 Arapahoe Road, Winter Park, Co 80482, Us, Winter Park, United States Show map

The 2-bedroom Cozy Condo On Vasquez Creek W/ Free Shuttle Access Winter Park villa is located 3.5 km from Fraser Tubing Hill and provides hiking for active guests. Offering a wellness facility, this… More

From US$ 517 Book Now

Skiing Sanctuary

19 Cedar Drive, Winter Park, United States Show map

Up to 6 guests can stay at the 2-bedroom Skiing Sanctuary Winter Park villa and enjoy Endeavour Lift, located approximately 5 minutes' walk away. Guests can enjoy snow skiing and fisheries at this… More

From US$ 706 Book Now

Winter Park Condo W/ Sleeping Loft - Near Main St

145 Arapahoe Rd Unit 203, Winter Park, United States Show map

The welcoming Winter Park Condo W/ Sleeping Loft - Near Main St villa is located 3.5 km from Main Street and welcomes its guests to enjoy hiking. Offering balloon rides, this 2-bedroom holiday home… More

From US$ 207 Book Now

Hot Tub Mountain Views Steps To Trails

815 Bear Trail, Winter Park Co 80482, Winter Park, United States Show map

The spacious Hot Tub Mountain Views Steps To Trails Apartment Winter Park features a convenient location 10 minutes' drive from Cabriolet and hosts up to 8 guests. Providing a Jacuzzi, this apartment… More

From US$ 478 Book Now

Luxury Villa 835 I Hot Tub I Great Views I Best Price I Free Adventures Daily

835 Bear Trail, Winter Park, United States Show map

The 4-bedroom Luxury Villa 835 I Hot Tub I Great Views I Best Price I Free Adventures Daily Winter Park is located approximately a 10-minute ride from Winter Park Resort and provides a Jacuzzi. The… More

From US$ 779 Book Now

Slopeside Villa 126 I Ski Views I Private Hot Tub I Bunks I Steam Shower I Discounted Attractions

126 Cedar Drive, Winter Park, United States Show map

Situated within 10 minutes' walk of Main Street, the 3-bedroom Slopeside Luxury Villa: Resort-Adjacent with Steam Shower & Activity Perks Winter Park entices guests with snow skiing and mini golf in… More

From US$ 652 Book Now

Slopeside Chalet 136 I Great Views I Steam Shower I Bunk Room I Discounted Attractions

136 Cedar Dr., Winter Park, United States Show map

The 3-bedroom Slopeside Luxury Villa: Ski Views & Activity Perks Winter Park entices guests to enjoy snow skiing and mini golf and offers proximity to Main Street, located about a 10-minute stroll… More

From US$ 1517 Book Now

Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I Free Adventures Daily

71 Balsam Dr., Winter Park, United States Show map

Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I Free Adventures Daily Winter Park is located about a 20-minute walk from Coca Cola Tubing Hill At Winter Park and provides… More

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Luxury Villa 745I Hot Tub I Great Views I Best Price I Free Adventures Daily

745 Bear Trail, Winter Park, United States Show map

During the stay at the 2-bedroom Luxury Villa 745I Hot Tub I Great Views I Best Price I Free Adventures Daily Winter Park, guests can indulge in snow skiing, mini golf, and cycling or visit the… More

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New Slopeside Luxury Villa 125 Hot Tub And Ski Views Best Price 500 Dollars Free Activities Daily

125 Balsam Drive, Winter Park, United States Show map

Featuring a Jacuzzi, the 3-bedroom New Slopeside Luxury Villa 125 Hot Tub And Ski Views Best Price 500 Dollars Free Activities Daily Winter Park is located approximately 10 minutes' walk from Main… More

From US$ 626 Book Now

Ski-In/Ski-Out Gemini Lift Access! Home W/ Hot Tub

145 Balsam Dr, Winter Park, United States Show map

Ski-In/Ski-Out Gemini Lift Access! Home W/ Hot Tub Winter Park enjoys a convenient location, a 12-minute walk from Winter Park Resort, and offers guests to unwind in a Jacuzzi. Guests can enjoy snow… More

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Bear Crossing 995

995 Bear Trail, Winter Park, United States Show map

Bear Crossing 995 Villa Winter Park is located 3.4 km from the outdoor sports store "Colorado Adventure Park" and provides snow skiing, hiking, and fisheries for active guests. More

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Mountainside Winter Park Ski Home W/ Hot Tub

105 Balsam Dr, Winter Park, United States Show map

The 4-bedroom Mountainside Winter Park Ski Home W/ Hot Tub is nestled approximately 5 minutes' walk from Amaze'n Mazes and entices guests with a Jacuzzi. Located 2.6 km from Discovery, this Winter… More

From US$ 558 Book Now

Slopeside Villa 135 I Private Hot Tub I Great Views I Activity Program

135 Balsam Dr., Winter Park, United States Show map

Suitable for 10 guests, the 3-bedroom Slopeside Luxury Villa: Hot Tub & Mountain Views Winter Park is located merely 10 minutes' walk from Main Street and provides a Jacuzzi for a relaxing stay. More

From US$ 393 Book Now

Walk To Winter Park Resort: Condo W/ Hot Tub!

1080 Winter Park Dr Unit 3, Winter Park, United States Show map

The 1-bedroom Walk To Winter Park Resort: Condo W/ Hot Tub! villa is nestled in close proximity to Main Street and can accommodate up to 2 guests. Featuring a Jacuzzi and a sauna, the holiday home is… More

From US$ 410 Book Now

Winter Park Place #18

1080 Winter Park Dr #18, Winter Park, United States Show map

Winter Park Place #18 apartment is located an 18-minute walk from Cabriolet and entices guests with a Jacuzzi and a sauna. At the spacious apartment, Wi-Fi and parking are also provided. More

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Winter Park Place #1

1080 Winter Park Dr #1, Winter Park, United States Show map

The spacious 150 m² Winter Park Place #1 apartment is just 600 metres from Main Street and can accommodate up to 8 guests. Winter Park Resort is only 0.8 km away, while Olympia Express is within 25… More

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Slopeside River Front Condo 15 I Hot Tub I Views I Bunk Room I Office I Discounted Attractions

1080 Winter Park Dr. #15, Winter Park, United States Show map

During the stay at Riverfront Ski Retreat: Luxury Condo with Hot Tub & Activity Perks Winter Park villa, guests can indulge in a hot tub or visit Coca Cola Tubing Hill At Winter Park, located an 18… More

From US$ 228 Book Now

Slopeside River Front Chalet I Hottub I Firepit I Views I Game Room I Bunks I Discounted Attractions

130 Balsam Dr., Winter Park, United States Show map

Situated merely a 7-minute walk from Main Street, Slopeside Luxury Chalet: Riverside Resort with Hot Tub & Activity Perks Winter Park offers a Jacuzzi and can accommodate up to 10 guests. Located… More

From US$ 907 Book Now

Winter Park Cabin - Walk To Main Street & Downtown

Winter Park, Co, 80482, Winter Park, United States Show map

Accommodating up to 8 guests, the 2-bedroom Winter Park Cabin - Walk To Main Street & Downtown is situated within 5 minutes' drive of renowned cultural sites such as Cozens Ranch House Museum. The… More

From US$ 359 Book Now

Slopeside Villa 90 I Hot Tub I Great Views I Bunk Room I Gas Firepit I Discounted Attractions

90 Trademark Dr. #90, Winter Park, United States Show map

Situated a mere 6 minutes' walk from Main Street, the 3-bedroom Slopeside Luxury Villa: Hot Tub, Views & Free Activities Winter Park offers a hot tub and can accommodate up to 8 guests. This 3… More

From US$ 394 Book Now

Beaver Village Unit #2032R

220 Village Drive Cr 702, Winter Park, United States Show map

Located 4 km from Coca Cola Tubing Hill At Winter Park, the 57 m² Beaver Village Unit #2032R Winter Park apartment overlooks the mountain. The apartment offers a Jacuzzi and a sauna for guests to… More

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Beaver Village Unit #2031

220 Village Drive, Building 20 Unit 2031, Winter Park, United States Show map

The 94 m² Beaver Village Unit #2031 Winter Park apartment is located in Winter Park, about 4 km from Coca Cola Tubing Hill At Winter Park, and boasts a Jacuzzi and a sauna. This 2-bedroom apartment… More

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Ski-In Ski-Out Condo At Zephyr Mountain Lodge 1518

401 Nystrom Lane, Winter Park, United States Show map

The excellent Ski-In Ski-Out Condo At Zephyr Mountain Lodge 1518 Winter Park hotel, located right near Main Street, is proud to feature a private art gallery. Facing mountain views, this 4-star… More

From US$ 546 Book Now

Winter Park Condo W/ Mountain Views + Hot Tub

401 Nystrom Ln #1424, Winter Park, United States Show map

Featuring a Jacuzzi, the 3-bedroom Winter Park Condo W/ Mountain Views + Hot Tub villa is located around a 10-minute walk from Winter Park Resort and can host up to 10 guests. Providing guests with… More

From US$ 573 Book Now

Zephyr Mountain Lodge 1420 Ski-In And Ski-Out

401 Nystrom Lane, Winter Park, United States Show map

Zephyr Mountain Lodge 1420 Ski-In And Ski-Out Winter Park offers proximity to nearby tourist spots, such as Main Street, situated 1.6 km away. More

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Slopeside Luxury Villa 82 I Hot Tub I Great Views I Best Price I Free Adventures Daily

82 Trademark Dr., Winter Park, United States Show map

Situated a mere 6 minutes' walk from Main Street, the 3-bedroom Slopeside Luxury Villa 82 I Hot Tub I Great Views I Best Price I Free Adventures Daily Winter Park offers a Jacuzzi and can accommodate… More

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Luxe Home Minutes To Skiing Hot Tub

20 Trademark Drive Unit 1, Winter Park, United States Show map

Located 8 minutes' walk from Main Street, the spacious Luxe Home Minutes To Skiing Hot Tub Winter Park apartment accommodates up to 8 guests. Set only a few steps from Amaze'n Mazes, this apartment… More

From US$ 839 Book Now

Silverado II Resort & Event Center

490 Kings Crossing Road, Winter Park, United States Show map

Silverado II Resort & Event Center Winter Park is located in Winter Park, 25 minutes' walk from Galloping Goose, and offers a heated pool. Wi-Fi in the rooms, a vending machine and a lift are… More

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4Br Mountain Escape Family Friendly Sleeps 10

387 Bear Trail, Winter Park, United States Show map

During the stay at the 4-bedroom 4Br Mountain Escape Family Friendly Sleeps 10 Villa Winter Park, guests can indulge in fisheries or visit Main Street, located around 4 km away. Featuring a hot tub… More

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Slopeside Chalet 100 I Hot Tub I Great Views I Bunk Room I Work Space I Discounted Attractions

100 Clover Lane (Kinney Way), Winter Park, United States Show map

Suitable for 10 guests, the 3-bedroom Slopeside Chalet 100 I Hot Tub I Great Views I Bunk Room I Work Space I Discounted Attractions Winter Park is located in close proximity to Main Street and… More

From US$ 787 Book Now