Killington, VT

Winding Way Chalet

3 bedrooms 5 beds 3 baths 8 guests New

About the property

Welcome to Winding Way Chalet: Your Ultimate Killington Retreat

Nestled amidst the rolling landscapes of Killington, Vermont, the Winding Way Chalet offers an enchanting mountain escape that embodies comfort and fun. This grand 3-level rental home, located off Route 100 in Killington, Vermont, is designed for groups and families seeking an unforgettable experience in the heart of ski country. Pet friendly too! (Fee applies, see below.

Sleeping Arrangements:
The chalet comfortably accommodates up to 8 guests with three large bedrooms, ensuring everyone has a peaceful retreat after a day of mountain adventures. Soft linens and warm, inviting decor create a haven of relaxation in each room.

Living Spaces:
The heart of the chalet is the stunning cathedral ceiling living room. This enormous space is bathed in natural light and features a majestic propane fireplace to gather around during chilly evenings. It's equipped with many bar amenities, perfect for crafting evening cocktails, and a smart cable TV to keep everyone entertained. There is a sitting area with a second smaller propane stove to enjoy. Challenge your companions to a game of pool on the billiards table, or simply sink into the plush sofas and enjoy the ambiance. Downstairs is a second cable TV with a PlayStation 4 (bring games to enjoy).

Kitchens and Dining:
Culinary enthusiasts will revel in not one, but two fully equipped kitchens – each adorned with modern appliances, cookware, and ample space to create sumptuous meals. Whether you're preparing a hearty breakfast before hitting the slopes or a festive dinner, our kitchens are set up to handle your needs with ease. Gather for meals in the spacious dining room, where memories are just waiting to be made.

Amenities:

  • Laundry Room: A convenient in-home laundry room means you can pack light and keep your favorite gear fresh throughout your stay.
  • Bathrooms: With three full bathrooms, morning routines and post-adventure clean-ups are hassle-free.
  • Generator: No worries if the power goes out!
  • Air Conditioning: Fully air-conditioned for summer
  • Garage: Protect your vehicle from the elements with access to a garage, providing security and warmth for your car.
  • Bathrooms: With three full bathrooms, morning routines and post-adventure clean-ups are hassle-free.

Outdoor Living:
Step out onto the deck and embrace the crisp mountain air while taking in the sweeping views. A grill awaits your BBQ cravings, and as the sun sets, gather around the propane fire pit to roast marshmallows and stargaze. It's the perfect ending to any day in Vermont.

Indoor Hot Tub Room:
After skiing or hiking, soothe your muscles in the privacy of your indoor hot tub room. It's a therapeutic experience no matter the season. (Hot tub included from mid-December to mid-March. Setup fee applies other times. See below.)

Explore Killington:
Located just a stone's throw from the best skiing, snowboarding, and mountain biking that Vermont has to offer, Winding Way Chalet is your gateway to outdoor adventure. In the warmer months, Killington's lush landscapes come alive with hikers, golfers, and those who simply wish to bask in the natural beauty of the region.

Book Your Stay:
Winding Way Chalet is more than just a place to stay – it's a destination that will host your laughter, adventures, and tranquil moments. Secure your dates now and step into a world where mountain charm meets luxury, and where your every comfort has been considered. This is not just a vacation; it's an experience that will linger in your heart long after you've departed. Welcome to your home away from home in Killington.

Bedding is as follows:

LOWER LEVEL
Room 1 - (1) full bed, (3) bunk beds.

MAIN FLOOR
Room 2 - (1) king bed.
Room 3 - (1) twin over full bunk bed.

• The hot tub is included for the peak ski season (late-December to mid-March). For other periods, there is an optional $195 set up fee. You understand use of hot tub is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless.
• Please be sure that you have entered the correct number of guests as we may have a per-person per-night surcharge to cover expenses. You can contact us for a custom quote before booking.
• Our minimum rental age is 25.
• We will provide you with door codes for our smart locks to come and go as you please and for contactless check in and out.
• We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge.
• Our entire home is non-smoking (e-cigs included). You may only smoke on the outdoor deck. There is a $500 fine for smoking in the house.
• You must e-sign and return our written rental agreement after you complete your booking.
• For your safety and ours, we have a camera on the house pointed at the driveway which records all the time. Cameras are not in any of the living areas.
• Quiet hours are from 10pm - 8am. We use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. Minut is 100% privacy compliant and is required on this property. If you have any questions, please ask. We are committed to your comfort so please let us know if we can do anything during your stay to make it more enjoyable.
• Fireworks are not permitted.
• Pets are considered. A $155 pet fee would apply.
• Please be advised that this property utilizes a ladder to access the bunk beds. By renting this property, you are agreeing to hold the owner and property manager harmless for any injury or death that is resulting from the use of the ladder.
• Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended.

SKI RESORTS: Killington Snowshed Base (6.9 miles), Killington K1 Base (7.3 miles), Pico Mountain (5.1 miles), Mountain Meadows Cross Country Skiing ( 3.7 miles)
GOLF: Killington Golf Course (6.8 miles), Green Mountain National Golf Course (1.8 miles)
NIGHTLIFE: Pickle Barrel (4.7 miles), Wobbly Barn (5.2 miles), Mary Lou's (5.8 miles), The Foundry at Summit Pond (4.3 miles), Rivershed (3.7 miles)
WEDDINGS: Killington Grand Resort (6.9 miles), The Birch Ridge (5.3 miles), Mountain Top Inn & Resort (16.1 miles)
AIRPORT: Rutland Regional Airport (19.9 miles), Burlington International Airport (76.3 miles), Albany International Airport (105 miles), Manchester-Boston Regional Airport (124 miles), Boston Logan (170 miles)

Welcome to Winding Way Chalet: Your Ultimate Killington Retreat

Nestled amidst the rolling landscapes of Killington, Vermont, the Winding Way Chalet offers an enchanting mountain escape that embodies comfort and fun. This grand 3-level rental home, located off Route 100 in Killington, Vermont, is designed for groups and families seeking an unforgettable experience in the heart of ski country. Pet friendly too! (Fee applies, see below.

Sleeping Arrangements:
The chalet comfortably accommodates up to 8 guests with three large bedrooms, ensuring everyone has a peaceful retreat after a day of mountain adventures. Soft linens and warm, inviting decor create a haven of relaxation in each room.

Living Spaces:
The heart of the chalet is the stunning cathedral ceiling living room. This enormous space is bathed in natural light and features a majestic propane fireplace to gather around during chilly evenings. It's equipped with many bar amenities, perfect for crafting evening cocktails, and a smart cable TV to keep everyone entertained. There is a sitting area with a second smaller propane stove to enjoy. Challenge your companions to a game of pool on the billiards table, or simply sink into the plush sofas and enjoy the ambiance. Downstairs is a second cable TV with a PlayStation 4 (bring games to enjoy).

Kitchens and Dining:
Culinary enthusiasts will revel in not one, but two fully equipped kitchens – each adorned with modern appliances, cookware, and ample space to create sumptuous meals. Whether you're preparing a hearty breakfast before hitting the slopes or a festive dinner, our kitchens are set up to handle your needs with ease. Gather for meals in the spacious dining room, where memories are just waiting to be made.

Amenities:

  • Laundry Room: A convenient in-home laundry room means you can pack light and keep your favorite gear fresh throughout your stay.
  • Bathrooms: With three full bathrooms, morning routines and post-adventure clean-ups are hassle-free.
  • Generator: No worries if the power goes out!
  • Air Conditioning: Fully air-conditioned for summer
  • Garage: Protect your vehicle from the elements with access to a garage, providing security and warmth for your car.
  • Bathrooms: With three full bathrooms, morning routines and post-adventure clean-ups are hassle-free.

Outdoor Living:
Step out onto the deck and embrace the crisp mountain air while taking in the sweeping views. A grill awaits your BBQ cravings, and as the sun sets, gather around the propane fire pit to roast marshmallows and stargaze. It's the perfect ending to any day in Vermont.

Indoor Hot Tub Room:
After skiing or hiking, soothe your muscles in the privacy of your indoor hot tub room. It's a therapeutic experience no matter the season. (Hot tub included from mid-December to mid-March. Setup fee applies other times. See below.)

Explore Killington:
Located just a stone's throw from the best skiing, snowboarding, and mountain biking that Vermont has to offer, Winding Way Chalet is your gateway to outdoor adventure. In the warmer months, Killington's lush landscapes come alive with hikers, golfers, and those who simply wish to bask in the natural beauty of the region.

Book Your Stay:
Winding Way Chalet is more than just a place to stay – it's a destination that will host your laughter, adventures, and tranquil moments. Secure your dates now and step into a world where mountain charm meets luxury, and where your every comfort has been considered. This is not just a vacation; it's an experience that will linger in your heart long after you've departed. Welcome to your home away from home in Killington.

Bedding is as follows:

LOWER LEVEL
Room 1 - (1) full bed, (3) bunk beds.

MAIN FLOOR
Room 2 - (1) king bed.
Room 3 - (1) twin over full bunk bed.

• The hot tub is included for the peak ski season (late-December to mid-March). For other periods, there is an optional $195 set up fee. You understand use of hot tub is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless.
• Please be sure that you have entered the correct number of guests as we may have a per-person per-night surcharge to cover expenses. You can contact us for a custom quote before booking.
• Our minimum rental age is 25.
• We will provide you with door codes for our smart locks to come and go as you please and for contactless check in and out.
• We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge.
• Our entire home is non-smoking (e-cigs included). You may only smoke on the outdoor deck. There is a $500 fine for smoking in the house.
• You must e-sign and return our written rental agreement after you complete your booking.
• For your safety and ours, we have a camera on the house pointed at the driveway which records all the time. Cameras are not in any of the living areas.
• Quiet hours are from 10pm - 8am. We use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. Minut is 100% privacy compliant and is required on this property. If you have any questions, please ask. We are committed to your comfort so please let us know if we can do anything during your stay to make it more enjoyable.
• Fireworks are not permitted.
• Pets are considered. A $155 pet fee would apply.
• Please be advised that this property utilizes a ladder to access the bunk beds. By renting this property, you are agreeing to hold the owner and property manager harmless for any injury or death that is resulting from the use of the ladder.
• Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended.

SKI RESORTS: Killington Snowshed Base (6.9 miles), Killington K1 Base (7.3 miles), Pico Mountain (5.1 miles), Mountain Meadows Cross Country Skiing ( 3.7 miles)
GOLF: Killington Golf Course (6.8 miles), Green Mountain National Golf Course (1.8 miles)
NIGHTLIFE: Pickle Barrel (4.7 miles), Wobbly Barn (5.2 miles), Mary Lou's (5.8 miles), The Foundry at Summit Pond (4.3 miles), Rivershed (3.7 miles)
WEDDINGS: Killington Grand Resort (6.9 miles), The Birch Ridge (5.3 miles), Mountain Top Inn & Resort (16.1 miles)
AIRPORT: Rutland Regional Airport (19.9 miles), Burlington International Airport (76.3 miles), Albany International Airport (105 miles), Manchester-Boston Regional Airport (124 miles), Boston Logan (170 miles)

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jun 19, 2026$327Available2
Jun 20, 2026$327Available2
Jun 21, 2026$327Available2
Jun 22, 2026$327Available2
Jun 23, 2026$327Available2
Jun 24, 2026$327Available2
Jun 25, 2026$327Available2
Jun 26, 2026$327Available2
Jun 27, 2026$327Available2
Jun 28, 2026$327Available2
Jun 29, 2026$327Available2
Jun 30, 2026$327Available2
Jul 1, 2026$327Available2
Jul 2, 2026$327Available2
Jul 3, 2026$327Available2
Jul 4, 2026$327Available2
Jul 5, 2026$327Available2
Jul 6, 2026$327Available2
Jul 7, 2026$327Available2
Jul 8, 2026$327Available2
Jul 9, 2026$327Available2
Jul 10, 2026$327Available2
Jul 11, 2026$327Available2
Jul 12, 2026$327Available2
Jul 13, 2026$327Available2
Jul 14, 2026$327Available2
Jul 15, 2026$327Available2
Jul 16, 2026$327Available2
Jul 17, 2026$327Available2
Jul 18, 2026$327Available2
Jul 19, 2026$327Available2
Jul 20, 2026$327Available2
Jul 21, 2026$327Available2
Jul 22, 2026$327Available2
Jul 23, 2026$327Available2
Jul 24, 2026$356Available2
Jul 25, 2026$352Available2
Jul 26, 2026$327Available2
Jul 27, 2026$327Available2
Jul 28, 2026$327Available2
Jul 29, 2026$327Available2
Jul 30, 2026$327Available2
Jul 31, 2026$348Available2
Aug 1, 2026$338Available2
Aug 2, 2026$327Available2
Aug 3, 2026$327Available2
Aug 4, 2026$327Available2
Aug 5, 2026$327Available2
Aug 6, 2026$327Available2
Aug 7, 2026$351Available2
Aug 8, 2026$342Available2
Aug 9, 2026$327Available2
Aug 10, 2026$327Available2
Aug 11, 2026$327Available2
Aug 12, 2026$327Available2
Aug 13, 2026$327Available2
Aug 14, 2026$343Available2
Aug 15, 2026$336Available2
Aug 16, 2026$327Available2
Aug 17, 2026$327Available2
Aug 18, 2026$327Available2
Aug 19, 2026$327Available2
Aug 20, 2026$327Available2
Aug 21, 2026$334Available2
Aug 22, 2026$340Available2
Aug 23, 2026$327Available2
Aug 24, 2026$327Available2
Aug 25, 2026$327Available2
Aug 26, 2026$327Available2
Aug 27, 2026$327Available2
Aug 28, 2026$334Available2
Aug 29, 2026$327Available2
Aug 30, 2026$327Available2
Aug 31, 2026$327Available2
Sep 1, 2026$327Available2
Sep 2, 2026$327Available2
Sep 3, 2026$347Available2
Sep 4, 2026$477Available2
Sep 5, 2026$488Available2
Sep 6, 2026$451Available2
Sep 7, 2026$351Available2
Sep 8, 2026$327Available2
Sep 9, 2026$327Available2
Sep 10, 2026$375Available2
Sep 11, 2026$447Available2
Sep 12, 2026$425Available2
Sep 13, 2026$329Available2
Sep 14, 2026$327Available2
Sep 15, 2026$327Available2
Sep 16, 2026$334Available2
Sep 17, 2026$548Available2

Amenities

Gym
Game Room
Fire place
Mountain view
Air conditioning
Dryer
Washer
Laundromat nearby

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Where you'll be

Killington, VT, 5751, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 5:00 PM.
Check-out before 10:00 AM.
Maximum 8 guests.