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Winter Park Rentals

From $302 per night (USD)
VRBO
Luxury Winter Park Condo |Downtown| Private Hot Tub!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: This wonderful cabin inspired getaway is a brand-new condo just outside of downtown Winter Park. The kitchen i ...
From $302 per night (USD)
VRBO
From $1131 per night (USD)
Expedia
The Summit Lodge: Views, Hot Tub & Bike Trails
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Winter Park Short Term Rental Registration NO. 022462 Welcome to Lakota Townhomes, where ski-town vibes meet modern comf ...
From $1131 per night (USD)
Expedia
From $288 per night (USD)
VRBO
Paws & Relax in Downtown Winter Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to our tranquil 3rd-floor condo nestled at the rear of the Hi Country Haus complex, offering serene wooded mount ...
From $288 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Come experience The Antelope Room at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Oh, deer! The views may make it hard to get out of the cozy, yet luxurious queen bed. The steam shower makes for a refr ...
From $234 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Bike Park Paradise with Epic Resort Views
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Winter Park Short Term Rental Registration NO. 019190 Experience the epitome of mountain luxury at our Lakota neighborh ...
From $417 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Beautiful Condo at Winter Park!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Beautiful one bedroom condo that sleeps up to 6 and situated at one of the best locations at Iron Horse Condominiums. A ...
From $147 per night (USD)
Expedia
$Bike Trails | Hot Tub w\/ Mountain Views!$
From $408 per night (USD)
VRBO
Bike Trails | Hot Tub w\/ Mountain Views!
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Winter Park Short Term Rental Registration NO. 022458 Welcome to our luxurious mountain retreat, where indulgence meets ...
From $408 per night (USD)
VRBO
From $632 per night (USD)
Expedia
New Luxury Villa 85 I Hot Tub I Rooftop Lounge I Views I Best Price I FREE Adventures Daily
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $632 per night (USD)
Expedia
From $316 per night (USD)
VRBO
Come experience The Goat Room at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
G.O.A.T. + Llama Loft This room may be one of the greatest hotel rooms because of the very special llama loft. Extra sp ...
From $316 per night (USD)
VRBO
From $333 per night (USD)
Expedia
Get cozy in The Bear Suite at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Un-bearable views! The king size retreat has it all, space to lounge, a walk-in closet, mini-fridge, coffee station, do ...
From $333 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Get cozy in The Bighorn Sheep Room at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Made for ewe! A luxurious king and queen bed makes this room great for a group up to 4. Room features a mini-fridge, co ...
From $308 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Come experience The Elk Room at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Buck wild! The vaulted ceilings, picture perfect views of town and secret cub cave make this room un-herd of. Also feat ...
From $325 per night (USD)
Expedia
From $464 per night (USD)
VRBO
Get cozy in The Bison Suite at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Bison, Buffalo, Tatanka A ton of fun! This is our premier one-bedroom suite with a fully equipped kitchen. The living a ...
From $464 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Come experience The Fox Room at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay foxy! A perfect room for one or two guests. We love the fireplace, the private entrance and cozy, yet luxurious ki ...
From $239 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Get cozy in The Moose Suite at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Duck, duck, moose! One of our largest rooms and the only one on the main level, Moose features two queen beds, a walk-i ...
From $355 per night (USD)
VRBO
From $195 per night (USD)
Expedia
Get cozy in The Snowshoe Hare Room at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Hopping good times! We love the fireplace, the private entrance and cozy, yet luxurious queen bed. Room features a mini ...
From $195 per night (USD)
Expedia
From $235 per night (USD)
VRBO
Come experience The Marmot Room at Winter Park's only luxury boutique hotel!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Small but mighty! Nothing clever here for our small, but mighty room. We love the private entrance and luxurious king b ...
From $235 per night (USD)
VRBO
From $209 per night (USD)
Expedia
Luxe Townhome | Private Hot Tub & Amazing Views
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Summary: Welcome to our exquisite newly listed luxury townhome, nestled less than 5 miles away from the world-renowned W ...
From $209 per night (USD)
Expedia
From $405 per night (USD)
VRBO
Bikes, Views, & Comfort: Winter Park Condo Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Winter Park Short Term Rental Registration NO. 008306 Luxury condo in the heart of Old Town Winter Park. Nestled amids ...
From $405 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Ski In Ski Out | Zephyr Mountain Lodge 2219 | Hot Tub | Base Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Zephyr Mountain Lodge 2219 is a serene condo located right at the slopes and base area village. This updated condo is pe ...
From $205 per night (USD)
Expedia
Click For Pricing
VRBO
Arapahoe Mountain Escape with Private Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Arapahoe Mountain Escape Welcome to your secluded mountain retreat! This expansive four-bedroom home promises breathtaki ...
Click For Pricing
VRBO
From $154 per night (USD)
Expedia
Modern slopeside out studio with access to hot tub, fire pit & fire place
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Additionally, at times there will be construction noise, possible Mondays-Saturdays (allowed work hours 7 am to 7 pm), w ...
From $154 per night (USD)
Expedia
From $818 per night (USD)
VRBO
Rock & Stars Chalet: Mountain Luxury, Ski Locker
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
STR# 022460 STR# 022460 Welcome to Rock and Stars Chalet—where mountain luxury intertwines with thrilling adventure! Wh ...
From $818 per night (USD)
VRBO
$Ski-In\/Ski-Out Winter Park Condo w\/ Mountain Views$
From $282 per night (USD)
Expedia
Ski-In\/Ski-Out Winter Park Condo w\/ Mountain Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Trade the typical hustle and bustle for alpine adventures on a stay at this Winter Park vacation rental! Boasting a prim ...
From $282 per night (USD)
Expedia
$Ski-In\/Ski-Out Winter Park Condo w\/ Balcony!$
From $178 per night (USD)
VRBO
Ski-In\/Ski-Out Winter Park Condo w\/ Balcony!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to the Rocky Mountains and experience the best of Winter Park at this inviting vacation rental! Boasting an updat ...
From $178 per night (USD)
VRBO
$Gorgeous all-season townhome with private hot tub, two decks, fireplace, & W\/D$
From $637 per night (USD)
Expedia
Gorgeous all-season townhome with private hot tub, two decks, fireplace, & W\/D
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Cabin Sweet Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $637 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Spacious 2 bedroom home with hot tub
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Rent our lovely 2 bedroom home, great amenities, spacious floor plan. Close to the main downtown area of Winter Park, q ...
From $290 per night (USD)
VRBO
From $272 per night (USD)
Expedia
Premium Unit 1301 - 1 Bedroom - Zephyr Mtn Lodge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just 110 feet from the gondola, for the closest stay to mountain adventure, this is a perfect property for you! ...
From $272 per night (USD)
Expedia
$Select Unit 3606 - Fraser Crossing\/Founders Pointe$
From $403 per night (USD)
VRBO
Select Unit 3606 - Fraser Crossing\/Founders Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located just 150 yards from the base of Winter Park Resort, so close you can see when the gondola opens. **The s ...
From $403 per night (USD)
VRBO
$Downtown Winter Park Condo w\/ Free Bus to Ski Base$
From $194 per night (USD)
Expedia
Downtown Winter Park Condo w\/ Free Bus to Ski Base
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Nestled in the heart of downtown Winter Park, this exquisite 2-bedroom, 1-bath vacation rental offers an unparalleled bl ...
From $194 per night (USD)
Expedia
From $406 per night (USD)
VRBO
Luxury Chalet 100 I Hot Tub I Great Views I Arcade I FREE Adventures Daily
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $406 per night (USD)
VRBO
$Ski-In\/Ski-Out Cozy Studio Retreat at Winter Park Resort$
Click For Pricing
Expedia
Ski-In\/Ski-Out Cozy Studio Retreat at Winter Park Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Wake up and make breakfast in the fully appointed kitchen. Walk out and enjoy your meal on the expansive shared patio wh ...
Click For Pricing
Expedia
From $159 per night (USD)
VRBO
3rdf-floor condo next to rec center with indoor pool, hot tubs, gym, fireplace
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hi Country Haus Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $159 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Cozy Winter Park Studio: Walk to Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Retreat to the Rockies when you stay at this 1-bathroom studio, situated within walking distance to après-ski breweries ...
From $172 per night (USD)
Expedia
From $264 per night (USD)
VRBO
✻ Ski In Ski Out | Base Area @ WP | Zephyr Mountain Lodge 1417 | Great Central Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This one-level condo located right in the Village at Winter Park is a perfect escape for those looking to get away from ...
From $264 per night (USD)
VRBO
From $1315 per night (USD)
Expedia
Luxury Villa 510 I Next To Resort I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $1315 per night (USD)
Expedia
$Downtown Winter Park Condo w\/ Community Hot Tub$
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VRBO
Downtown Winter Park Condo w\/ Community Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience Colorado like never before with a stay at this upscale 3-bedroom, 3-bathroom vacation rental in Winter Park. ...
Click For Pricing
VRBO
From $482 per night (USD)
Expedia
Rocky Revel! New! Luxury Condo DT Winter Park with FREE Shuttle to the Slopes!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Rocky Revel! Don't let the lack of reviews deter you! We recently bought this newly built condo and this is o ...
From $482 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Cozy Condo In Town - On Blue Bus Route to Resort - Walk to Restaurants & Grocery
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cute, cozy condo in Winter Park proper On the blue bus route - https://www.theliftwp.com/route-selector-page Walk to res ...
From $151 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Arrow 201 Downtown Winter Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Arrow 201 in Downtown Winter Park Experience the charm of this well-lit, spacious 2-bedroom, 2-bathroom condo nestled ...
From $306 per night (USD)
Expedia
From $178 per night (USD)
VRBO
90 Hideaway Unit 10 just steps to National Forest Trails
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Remodeled Condo just steps to National Forest Trails This charmingly renovated condominium, just a stone's th ...
From $178 per night (USD)
VRBO
Click For Pricing
Expedia
Family-sized Winter Park condo with heated pool, hot tub and game room!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located a block off Main Street in the beautiful mountain town of Winter Park, Colorado, Lions Gate is a short walk away ...
Click For Pricing
Expedia
From $502 per night (USD)
VRBO
Designer Condo | Hot Tub Access + Vista Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sanctuary of Silverado | Mountainside Elegance in the Heart of Winter Park Unwind in style at Sanctuary of Silverado, a ...
From $502 per night (USD)
VRBO
From $166 per night (USD)
Expedia
Winter Haus! 2 Bedroom Corner Unit in the heart of Winter Park, Colorado.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Winter Haus! This unique unit combines all the best that Winter Park has to offer. Nestled steps away from th ...
From $166 per night (USD)
Expedia
From $450 per night (USD)
VRBO
The Winter Baker. Near the slopes and Walk to Downtown Winter Park!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to your ideal Winter Park getaway situated in the heart of downtown. Telemark, the building housing this condo, ...
From $450 per night (USD)
VRBO
From $1031 per night (USD)
Expedia
Mary Jane's Dream Home | A True HGTV Dream Home | Private Luxe Lodge
Bedrooms:
5
Bathrooms:
5
Sleeps:
14
- Please note, this home does not have air conditioning, but there is a ceiling fan or portable fan in each room. Welco ...
From $1031 per night (USD)
Expedia
From $889 per night (USD)
VRBO
Walk to Winter Park Lifts - Private Hot Tub - Pet Friendly - Custom Duplex
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Nestled in the pines and surrounded by soaring peaks, Winter Walk is a vintage chalet with easy access to all of the act ...
From $889 per night (USD)
VRBO
$Ski-In\/Out Condo w\/ Trails, Pool & Hot Tub$
From $279 per night (USD)
Expedia
Ski-In\/Out Condo w\/ Trails, Pool & Hot Tub
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: Perfect summer escape in Winter Park! Ride or hike right from your door with access to mountain trails. Relax w ...
From $279 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Select Unit 1709 - 2BR - Zephyr Mountain Lodge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Just 110 feet from the gondola, for the closest stay to mountain adventure, this is a perfect property for you! ...
From $355 per night (USD)
VRBO
From $330 per night (USD)
Expedia
Upscale condo with full kitchen & shared hot tub - walk to gondola
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Zephyr Mountain Lodge #1511 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $330 per night (USD)
Expedia
From $844 per night (USD)
VRBO
New Luxury Villa 211 I Next To Resort I Hot Tub I Views I Best Price I FREE Adventures Daily
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $844 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Mountainview Retreat: Bikes, River & Hot Tub
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Winter Park Short Term Rental Registration No. 024026 Welcome to our alpine oasis overlooking the breathtaking Winter P ...
From $374 per night (USD)
Expedia
From $422 per night (USD)
VRBO
New Slopeside Luxury Villa 125 I Hot Tub I Ski Views I Best Price I FREE Adventures Daily
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $422 per night (USD)
VRBO
From $831 per night (USD)
Expedia
Trademark Views | Luxe Soaks & Mountain Views
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Trademark Views | Panoramic Luxury Near Winter Park Resort Soaring ceilings, majestic views, and the perfect après-hike ...
From $831 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Steps from Hideaway Park | Music & Mountain Vibes
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Winter Park Short Term Rental Registration NO. 024020 Discover Antlers Run at Trailhead lodge, ideal Location behind Hid ...
From $298 per night (USD)
VRBO
From $464 per night (USD)
Expedia
Cozy Winter Park Stay Perfect for Group Travelers | 2 Units | Hot Tubs Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $464 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Winter Park Getaway: Cozy Family-Friendly Room Available, Hotel with Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $230 per night (USD)
VRBO
From $515 per night (USD)
Expedia
King & Bunk, Gravity Haus, Near Downtown, 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $515 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Powder Hound, Gravity Haus Winter Park, Ideal Skier’s Retreat, Gym Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $207 per night (USD)
VRBO
From $196 per night (USD)
Expedia
Rambler Single King, Gravity Haus Winter Park, Gym Access, Downtown Ease
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $196 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Ski In Out Luxury Condo 2403 I Hot Tub I Gym I Ski Views I Best Price I FREE Adventures Daily
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $296 per night (USD)
VRBO
From $206 per night (USD)
Expedia
Modern Stay Near Downtown Winter Park with Hot Tubs & Gym Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $206 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Idlewild King + Twin Bunks, Gravity Haus Winter Park, Outdoor Hot Tub, Central
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $258 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Relaxing Mountain Retreat Ideal for Couple Stay | Skiing or Hike Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $282 per night (USD)
Expedia
From $254 per night (USD)
VRBO
Catwalk Double Queen + Bunks, Gravity Haus Winter Park, Mountain Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $254 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Winter Park Family Escape: Modern Room with Downtown Access | Outdoor Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover vibrant Winter Park! Immerse in lively downtown beats, epic skiing adventures, and serene mountain trails—all s ...
From $232 per night (USD)
Expedia
From $620 per night (USD)
VRBO
Luxury Condo | Near Gondola + Trail Access
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Ski & Chill | Your Mountain-View Escape Near Winter Park Resort Welcome to Ski & Chill, a luxury 3-bedroom retr ...
From $620 per night (USD)
VRBO
$Hike, Bike, Ski: Winter Park Condo w\/ Deck$
From $186 per night (USD)
Expedia
Hike, Bike, Ski: Winter Park Condo w\/ Deck
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Serene Views | Private Deck | In-Unit Laundry | Family Friendly Discover the perfect escape in Winter Park when you sta ...
From $186 per night (USD)
Expedia
From $593 per night (USD)
VRBO
New Luxury Chalet 411 I Hot Tub I Great Views I Best Price I FREE Adventures Daily
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $593 per night (USD)
VRBO
$Cozy Ski-In\/Ski-Out Winter Park Condo w\/ Pool!$
From $365 per night (USD)
Expedia
Cozy Ski-In\/Ski-Out Winter Park Condo w\/ Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Iron Horse Resort | Private Balcony | On-Site Bus Stop Look forward to long days on the slopes and cozy nights by the f ...
From $365 per night (USD)
Expedia
From $536 per night (USD)
VRBO
Luxury Mtn Retreat: Family Friendly, Sleeps 10
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Summary: Welcome to Bear Trail Luxury Retreat! This modern mountain home, 2 minutes from Downtown Winter Park, features ...
From $536 per night (USD)
VRBO
From $561 per night (USD)
Expedia
Mountain View Townhome with Private Hot Tub, 2 Gas Fireplaces - Near Skiing
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bear Trail Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $561 per night (USD)
Expedia
From $203 per night (USD)
VRBO
Cute, comfy, well-stocked condo with gorgeous views close to bus stop.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the powder pad! Our place has all the details to make your mountain getaway a fantastic trip. With 2 inviti ...
From $203 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Exclusive Summer Haven: Winter Park Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Winter Park Short Term Rental Registration NO. 024018 Experience the ultimate Rocky Mountain getaway at this exceptional ...
From $304 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Select Unit 1710 - 2BR - Zephyr Mountain Lodge
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Gorgeous top floor two bedroom two bathroom condominium at Zephyr Mountain Lodge. Custom cabinets, stainless steel appl ...
From $348 per night (USD)
VRBO
From $722 per night (USD)
Expedia
Hot Tub Soaks, Rooftop Views & Arcade Fun
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Basecamp Luxe | Where Mountain Style Meets Summer Adventure Welcome to Basecamp Luxe, a bold and beautifully reimagined ...
From $722 per night (USD)
Expedia
From $280 per night (USD)
VRBO
Hideaway Park Gem: Pool, Views, Music!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled beside Hideaway Park in downtown Winter Park, our condo provides the perfect blend of relaxation and adventure. ...
From $280 per night (USD)
VRBO
From $652 per night (USD)
Expedia
4BR Mountain Escape Family Friendly, Sleeps 10
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Summary: Escape to the mountains in a modern, upscale home 2 minutes from Downtown Winter Park that features 4BR/3.5BA, ...
From $652 per night (USD)
Expedia
$Luxury Modern Condo w\/ Hot Tub and Views!$
From $452 per night (USD)
VRBO
Luxury Modern Condo w\/ Hot Tub and Views!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Winter Park Short Term Rental Registration NO. 024870 Experience the perfect blend of luxury and convenience in this stu ...
From $452 per night (USD)
VRBO
From $356 per night (USD)
Expedia
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
***BRAND NEW LISTING***Discover your perfect mountain retreat in our beautifully furnished 3-bedroom, 3.5-bathroom townh ...
From $356 per night (USD)
Expedia
From $453 per night (USD)
VRBO
Lakota Lookout private hot tub
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Lakota Lookout Mountain View Townhome | Hot Tub Welcome to your ideal mountain retreat in Winter Park, Colorado! This ...
From $453 per night (USD)
VRBO
From $221 per night (USD)
Expedia
WinterPark*Ski*CoffeeBar*Pets+*CommunalHotTub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Cozy Winter Park Abode: Your ideal alpine retreat just 3 miles from Winter Park Ski Resort! This designer condo offers m ...
From $221 per night (USD)
Expedia
From $331 per night (USD)
VRBO
NEW LISTING! Value Unit 1422 - 2BR - Zephyr Mountain Lodge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay just 110 feet from the gondola for unbeatable access to mountain adventures! This cozy two-bedroom, two-bathroom c ...
From $331 per night (USD)
VRBO
From $1580 per night (USD)
Expedia
Canopy House | A Stunning Ski In Ski Out Masterpiece
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
Discover unparalleled mountain living at Canopy House, a mountain haven nestled amongst the trees in Winter Park. This l ...
From $1580 per night (USD)
Expedia
From $259 per night (USD)
VRBO
Cozy Rustic Condo with Scenic Views & Modern Amenities in Winter Park
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Viking Alpine Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $259 per night (USD)
VRBO
From $434 per night (USD)
Expedia
210 Sawyer with Private Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
No matter the season—winter, spring, summer, or fall—you'll love our newly renovated mountain retreat. In winter, you're ...
From $434 per night (USD)
Expedia
From $469 per night (USD)
VRBO
4-bedroom Modern Mtn Vacation
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A Stylish Escape w/ excellent location to all Winter Park and Fraser has to offer. 4 miles to Winter Park Resort, ~20 mi ...
From $469 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Comfy condo next to Gondola
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to your perfect mountain getaway! Nestled in the heart of the charming Winter Park Ski Resort, our comfy Condo o ...
From $342 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Peaceful 1-bedroom mountain condo in Winter Park
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Relax in this cozy and stylish retreat after enjoying a day in the mountains. The spacious and updated one-bedroom cond ...
From $149 per night (USD)
VRBO
$New 2BD\/2BA Condo - in Winter Park! Walk to restaurants & steps from bus line!$
From $379 per night (USD)
Expedia
New 2BD\/2BA Condo - in Winter Park! Walk to restaurants & steps from bus line!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Brand new build in Timber Fox/ROAM community with fully stocked gourmet kitchen that opens up to the living and dining a ...
From $379 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Trailhead 322 Shared Hot Tub, Pool, Private Balcony, and Grill
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Accommodating up to eight guests, the condo includes two bedrooms and a hallway sleeping nook. The master bedroom featur ...
From $230 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Comfortable 3 bedroom, private deck, close to downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This charming and welcoming townhome, featuring an in-home sauna, offers ample space and a retro aesthetic, making it an ...
From $283 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Luxury Villa 308 I Next To Resort I Hot Tub I Great Views I Best Price I FREE adventures Daily
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Exclusive Complimentary Adventures! Winter Park Escapes is the only management company to provide Free activities and eq ...
From $633 per night (USD)
VRBO
Click For Pricing
Expedia
Music-Themed Luxury 4BR Chalet w Deck, Winter Park
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This beautiful custom 4-bedroom, music-themed condo offers an unbeatable blend of style, comfort, and mountain adventure ...
Click For Pricing
Expedia
From $321 per night (USD)
VRBO
Downtown Winter Park Gem | Walk to Everything!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Winter Park Short Term Rental Registration NO. 024872 Escape to this serene and modern second-floor condo in the heart o ...
From $321 per night (USD)
VRBO
From $897 per night (USD)
Expedia
Rocky Mountain Retreat | Top-Notch Rooftop & Views
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This brand-new, custom-built 4-bedroom, 3.5-bathroom mountain home offers the perfect blend of upscale design and cozy m ...
From $897 per night (USD)
Expedia
$Newly Updated 3B\/2B, Walk to Restaurants, 50 Steps to Ski Shuttle.$
From $254 per night (USD)
VRBO
Newly Updated 3B\/2B, Walk to Restaurants, 50 Steps to Ski Shuttle.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Warm & newly-updated 3-bedroom condo. With a queen bed in two of the bedrooms and 2 bunk beds (one full, three twins) in ...
From $254 per night (USD)
VRBO
From $290 per night (USD)
Expedia
Winter Park Condo on the River: Walk to Downtown!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Riverview where you will enjoy privacy and beautiful views of the Fraser River from this stylish retreat. Th ...
From $290 per night (USD)
Expedia
From $782 per night (USD)
VRBO
Lakota Dreamcatcher South | Hot Tub | Across From Resort
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Escape to this stunning four bedroom home located in the exclusive Lakota neighborhood, just minutes from Winter Park Re ...
From $782 per night (USD)
VRBO
From $274 per night (USD)
Expedia
Winter Park Studio: On the River~ Walk Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Fireside Haven is a cozy studio located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downto ...
From $274 per night (USD)
Expedia

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