1+ Vacation Rentals Near Winding Trail |
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Luxury Home Villas - Vacation Rentals in Winding Trail

Resort Living: Pool, Hot-Tub, Game Room, near CU
New
From US $1,881
         

New
Villa
Resort Living: Pool, Hot-Tub, Game Room, near CU
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  • Parking
  • Pool

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Luxury Places to Stay in Winding Trail

Over 733+ Luxury Places to Stay in or Near Winding Trail
Outdoor Living! Hot Tub+Fire Pit+Gardens+GameRoom! Close to it ALL! From US $5,249
         

New
House
Outdoor Living! Hot Tub+Fire Pit+Gardens+GameRoom! Close to it ALL!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxurious, Renovated Craftsman in the Heart of Boulder From US $4,034
         

10.0 (7 Reviews)
House
Luxurious, Renovated Craftsman in the Heart of Boulder
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Desirable modern house, steps to Sanitas loop trail and walk to downtown Boulder From US $3,385
         

10.0 (7 Reviews)
House
Desirable modern house, steps to Sanitas loop trail and walk to downtown Boulder
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Modern, Art-filled, Downtown Oasis with Pool and Bocce - 3 blocks to Pearl St - From US $2,958
         

10.0 (2 Reviews)
House
Modern, Art-filled, Downtown Oasis with Pool and Bocce - 3 blocks to Pearl St -
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  • Pool

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Stylish Home with Outdoor Oasis, Steps to CU Campus From US $2,886
         

10.0 (2 Reviews)
House
Stylish Home with Outdoor Oasis, Steps to CU Campus
  • Parking
  • TV
  • Balcony/Terrace

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Your Perfect CU Graduation Headquarters: Walk to Folsom & Pearl St!
New
From US $2,868
         

New
House
Your Perfect CU Graduation Headquarters: Walk to Folsom & Pearl St!
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Chic Gem with Game Room, 5-Min Drive to Pearl St & CU
New
From US $2,864
         

New
House
Chic Gem with Game Room, 5-Min Drive to Pearl St & CU
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The Fantastic Classic Family Home in Boulder ⭐️ Great location, comfort & value! From US $2,706
         

10.0 (9 Reviews)
House
The Fantastic Classic Family Home in Boulder ⭐️ Great location, comfort & value!
  • Air Conditioner
  • Parking
  • TV

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Top-Rated Vacation Rentals with a Pool in Winding Trail

Over 127+ Top-Rated Vacation Rentals with a Pool in or Near Winding Trail
Walk to Pearl Street- With Great Backyard! From US $781
         

10.0 (95 Reviews)
House
Walk to Pearl Street- With Great Backyard!
  • Air Conditioner
  • Parking
  • Pet Friendly

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As Seen On TV: Boulder Mountain Retreat - 6 Bedroom, Walkable to Pearl, 2 acres From US $1,241
         

10.0 (59 Reviews)
House
As Seen On TV: Boulder Mountain Retreat - 6 Bedroom, Walkable to Pearl, 2 acres
  • Air Conditioner
  • Parking
  • Pet Friendly

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BEAUTIFUL 1 BEDROOM CONDO IN HISTORIC MAPLETON HILL 5 BLOCKS TO PEARL MALL From US $106
         

10.0 (23 Reviews)
Condo
BEAUTIFUL 1 BEDROOM CONDO IN HISTORIC MAPLETON HILL 5 BLOCKS TO PEARL MALL
  • Air Conditioner
  • Parking
  • Pet Friendly

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Warm, inviting home, close to CU, downtown and mountains From US $723
         

10.0 (16 Reviews)
House
Warm, inviting home, close to CU, downtown and mountains
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Rooftop Pool, Mountain Views! Exec Rental @ The Peloton West From US $213
         

10.0 (16 Reviews)
Condo
Rooftop Pool, Mountain Views! Exec Rental @ The Peloton West
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Dream House - Hot Tub, 3 blocks from Pearl Street, and 5 outdoor patios From US $1,088
         

10.0 (11 Reviews)
House
Luxury Dream House - Hot Tub, 3 blocks from Pearl Street, and 5 outdoor patios
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  • Pool

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Exceptional Boulder Stay! Perfect Executive Style Home, high spd int, amenities From US $166
         

10.0 (11 Reviews)
Condo
Exceptional Boulder Stay! Perfect Executive Style Home, high spd int, amenities
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  • Pool

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Peaceful Paradise w/Flatiron view, gas fireplace, 30 D min, perfect for RELOn From US $143
         

10.0 (11 Reviews)
House
Peaceful Paradise w/Flatiron view, gas fireplace, 30 D min, perfect for RELOn
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  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Winding Trail

Over 229+ Pet-Friendly Vacation Rentals in or Near Winding Trail
Pet friendly in Boulder! Minutes from CU & Pearl! From US $319
         

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10.0 (1 Review)
House
Pet friendly in Boulder! Minutes from CU & Pearl!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hotel Boulderado From US $160
         

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9.6 (1654 Reviews)
Hotel
Hotel Boulderado
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  • Pet Friendly

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❤️Walk to the Heart of Pearl Street from this Charming Historic Home From US $598
         

10.0 (228 Reviews)
House
❤️Walk to the Heart of Pearl Street from this Charming Historic Home
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stroll to Pearl Street from Large, Stunning Historic Home With Private Yard From US $997
         

10.0 (61 Reviews)
House
Stroll to Pearl Street from Large, Stunning Historic Home With Private Yard
  • Air Conditioner
  • Parking
  • Pet Friendly

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Boulder Artist Home Mountain Views Garden Pet-Friendly From US $531
         

10.0 (18 Reviews)
House
Boulder Artist Home Mountain Views Garden Pet-Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sunny & Spacious North Boulder Home From US $893
         

10.0 (108 Reviews)
House
Sunny & Spacious North Boulder Home
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  • Parking
  • Pet Friendly

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Downtown Boulder Oasis. 3 Blocks from Pearl St Mall. 4 bedrooms and 2 full baths From US $609
         

10.0 (32 Reviews)
House
Downtown Boulder Oasis. 3 Blocks from Pearl St Mall. 4 bedrooms and 2 full baths
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  • Pet Friendly

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Pet-Friendly! Stunning Home — Steps to Downtown, CU & Hiking Trails. From US $1,304
         

10.0 (18 Reviews)
House
Pet-Friendly! Stunning Home — Steps to Downtown, CU & Hiking Trails.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Winding Trail

Over 78+ Large Vacation Homes & Villas in or Near Winding Trail
4 Bedrooms and 5 Beds with Game Room Only 5 min Drive to College and Perfect for Family's From US $523
         

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8.9 (7 Reviews)
House
4 Bedrooms and 5 Beds with Game Room Only 5 min Drive to College and Perfect for Family's
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful spacious home in heart of Boulder From US $1,304
         

10.0 (115 Reviews)
House
Beautiful spacious home in heart of Boulder
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Luxurious 6 bedroom Residence, A+ Outdoor spaces Walk to Pearl St, Mt. Sanitas From US $1,212
         

10.0 (12 Reviews)
House
Luxurious 6 bedroom Residence, A+ Outdoor spaces Walk to Pearl St, Mt. Sanitas
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5 minutes from campus. Stunning large home in beautiful neighborhood. From US $1,146
         

10.0 (7 Reviews)
House
5 minutes from campus. Stunning large home in beautiful neighborhood.
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Boulder Indoor-Outdoor Oasis From US $883
         

10.0 (4 Reviews)
House
Boulder Indoor-Outdoor Oasis
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Family-Friendly Home with Lush Backyard, 5-min to Downtown Boulder From US $1,303
         

10.0 (2 Reviews)
House
Family-Friendly Home with Lush Backyard, 5-min to Downtown Boulder
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  • Parking
  • Pet Friendly

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Stunning Historic Home in Downtown Boulder From US $1,046
         

10.0 (2 Reviews)
House
Stunning Historic Home in Downtown Boulder
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  • Pet Friendly

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Modern Residence Panoramic Views From US $1,500
         

10.0 (1 Review)
House
Modern Residence Panoramic Views
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Wheelchair Accessible Vacation Homes in Winding Trail

Over 64+ Wheelchair Accessible Vacation Homes in or Near Winding Trail
Central Boulder Studio Condo - Quiet Space Close to Downtown! From US $122
         

10.0 (3 Reviews)
Apartment
Central Boulder Studio Condo - Quiet Space Close to Downtown!
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  • Pool

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The Bradley Boulder Inn From US $199
         

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9.5 (149 Reviews)
Hotel
The Bradley Boulder Inn
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  • View

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Limelight Boulder From US $230
         

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9.8 (102 Reviews)
Hotel
Limelight Boulder
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  • Parking
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Modern 1-bedroom condo on Pearl Street, WiFi, AC, parking From US $621
         

10.0 (1 Review)
Condo
Modern 1-bedroom condo on Pearl Street, WiFi, AC, parking
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  • Parking
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Modern & Unique Pearl street condo From US $489
         

9.8 (31 Reviews)
Condo
Modern & Unique Pearl street condo
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* New * Modern Chic Studio/soaking tub/bike path From US $512
         

9.8 (14 Reviews)
House
* New * Modern Chic Studio/soaking tub/bike path
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  • Parking
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Boulder Flatirons Mansion From US $1,283
         

New
House
Boulder Flatirons Mansion
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1 Mi to CU Boulder! Walkable Condo w/Indoor Pool From US $290
         

New
Condo
1 Mi to CU Boulder! Walkable Condo w/Indoor Pool
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Winding Trail Varoom and Airbnb Places to Stay Under $200

Over 266+ Winding Trail Varoom and Airbnb Places to Stay Under $200
Newly remodeled bright open floor plan located in the heart of Boulder From US $107
         

10.0 (16 Reviews)
Condo
Newly remodeled bright open floor plan located in the heart of Boulder
  • Parking
  • TV
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Like Home but Better! A Boulder Favorite! From US $187
         

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9.6 (14 Reviews)
Apartment
Like Home but Better! A Boulder Favorite!
  • Air Conditioner
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  • Pet Friendly

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Residence Inn by Marriott Boulder Canyon Boulevard From US $161
         

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9.4 (682 Reviews)
Hotel
Residence Inn by Marriott Boulder Canyon Boulevard
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Fabulous Downtown Kitchen! From US $155
         

9.6 (68 Reviews)
Apartment
Fabulous Downtown Kitchen!
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Entire 2-Story Townhome in Central Boulder From US $170
         

9.8 (11 Reviews)
House
Entire 2-Story Townhome in Central Boulder
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Downtown Delight off Pearl street From US $94
         

10.0 (17 Reviews)
Condo
Downtown Delight off Pearl street
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Cheerful 2 Bdrm/1.5 Bath Pearl St. Condo From US $111
         

10.0 (7 Reviews)
Condo
Cheerful 2 Bdrm/1.5 Bath Pearl St. Condo
  • Air Conditioner
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LOWER winter rates! 1BD 1,000sf Private Suite, 2 blocks from Pearl St. From US $150
         

10.0 (3 Reviews)
House
LOWER winter rates! 1BD 1,000sf Private Suite, 2 blocks from Pearl St.
  • Parking
  • TV
  • Security/Safety

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Instantly Bookable Vacation Homes in Winding Trail

Over 280+ Instantly Bookable Vacation Homes in or Near Winding Trail
Chautauqua Park 5 Bedroom Home Blocks from Boulder's Majestic Flatirons From US $1,182
         

10.0 (145 Reviews)
House
Chautauqua Park 5 Bedroom Home Blocks from Boulder's Majestic Flatirons
  • Air Conditioner
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Bright & Modern | King Suite | Creekside Trail From US $529
         

8.8 (10 Reviews)
Condo
Bright & Modern | King Suite | Creekside Trail
  • Air Conditioner
  • Parking
  • Pool

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Canyon Urban Oasis in Central Boulder From US $451
         

10.0 (137 Reviews)
House
Canyon Urban Oasis in Central Boulder
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Walnut Mews - Quiet Creekside townhome next to Pearl Street From US $445
         

10.0 (158 Reviews)
House
Walnut Mews - Quiet Creekside townhome next to Pearl Street
  • Air Conditioner
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Private & Modern in Central Boulder near Downtown, CU & Google From US $380
         

10.0 (61 Reviews)
House
Private & Modern in Central Boulder near Downtown, CU & Google
  • Air Conditioner
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Your own inner Boulder home! Go to Pearl Street and hike! From US $202
         

8.8 (20 Reviews)
House
Your own inner Boulder home! Go to Pearl Street and hike!
  • Air Conditioner
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DOWNTOWNS BEST LOCATION Pied-à-terre From US $253
         

10.0 (221 Reviews)
Condo
DOWNTOWNS BEST LOCATION Pied-à-terre
  • Air Conditioner
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Clean, Downtown Boulder Luxury. ⛰ From US $305
         

10.0 (143 Reviews)
House
Clean, Downtown Boulder Luxury. ⛰
  • Air Conditioner
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  • TV

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About Winding Trail Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Luxuryhomevilla Winding Trail, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winding Trail. Places to stay near Winding Trail with prices averaging $1,881 a night.

Luxuryhomevilla makes it easy and safe to find and compare vacation rentals in Winding Trail with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Winding Trail

Type Count
Villas 1

Use these Quick Filters to Find a Vacation Rental in Winding Trail

★ Pro Tip: Luxuryhomevilla makes it easy to compare the best listings on Luxuryhomevilla homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxuryhomevilla homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winding Trail.

Weather in Winding Trail

View the weather forecast for Winding Trail before booking your Winding Trail Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F