Luxury Rental Homes

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ThreeBears – Views, Location

ThreeBears is a wonderful property boasting fantastic mountain views. Great location on the mountain with skiing to the left (Bear) and right (Snowshed, K1) of the home. This fantastic home is equipped with an outdoor hot tub, Tesla EV charger, giant TV, fully stocked kitchen and views from all three floors.

Living Room

TreeTops – Ski-Off Condo

This beautiful 4 bedroom (plus loft) ski-off unit was just renovated in 2021. Right next to the Killington Golf Course, and less than 1/2 mile from Killington’s popular Snowshed base area and learn-to-ski trails, the location is prime for accessing everything the area has to offer. Go from your private ski locker to the shuttle stop at the end of the driveway to access any base area without parking, and follow the Whiffletree trail off of Snowshed to come straight home at the end of the day.

livingroom

RoyalBear – Lux Chalet Retreat 

Stay at our grand skiing chalet right in the heart of Killington. Surround your family and friends with timeless style, while enjoying all the modern amenities, including gigabit internet and RokuTV. This house is well-positioned, nestled in the woods a few minutes from the slope, and right around the corner from The Garlic restaurant, The Pickle Barrel night spot, and the market.

BearVaria! – Close to it all!

Welcome to Bear-varia! A Bavarian themed chalet in the heart of Killington. Close to everything with a great location off the access road by the market. Perfect for friends and families with plenty of space to spread out. Inside there’s a fireplace, TV with Roku and fast fiber internet. Also a separate area for gaming and hanging out with a second TV with Nintendo, a PacMan arcade game and plenty of board games to make memories and connect. Outside, there is a large yard and outdoor dining.

livingroom

Happy Cub – In the heart of Killington

Beautiful location in the heart of Killington, just behind the Market and by Casey’s Caboose. Minutes to the slopes and walking distance to the restaurants, market and shuttle. Relax and connect with friends and family in this lovely 4BR, 2 Bath home. There are 2 floors for people to spread out, enjoy an eat in kitchen and open concept living room with huge Roku TV and Alexa. Downstairs, have fun in the game room, with arcade games, Nintendo, board games, foosball and air hockey. Fun for all!

DoubleDen – Entire House!

Fantastic location on Killington Road! This duplex, offered as the entire house with 6 bedrooms, 4 baths is directly across from the shuttle stop, and a few minutes from the main resort base. Walk to some of the best restaurants and night clubs. Relax in large outdoor hot tub, or play with the arcade games, foosball, or pool table. Enjoy streaming over the gigabit internet connection on the 75″ TV (or one of several others), or go retro with the 80’s VHS and console game areas downstairs.

SunBear – Ski on Ski off!

A perfect perch on the mountain for families & friends to gather and enjoy the outdoors. Enjoy ski-on, ski-off during the snow season as part of the Sunrise Village next to Killington Resort’s Bear Mountain base area. Quiet & relaxing during the summer – an ideal base for hiking, canoeing, apple picking, and taking in fall foliage. During the winter, ski down to the Sunrise Village lift, and ski off again straight to the condo. Enjoy streaming over the gigabit wifi while while the kids play.

CountryBear – Gorgeous Home

Enjoy a true Vermont experience in this home that is one of the original homes to the area. Built in 1850, this charming and gorgeous home is filled with antique touches that will make you feel relaxed and at ease. Set on almost 4 acres in the heart of Killington, this unique property has something for everyone. Enjoy the pool, the hot tub, the screened in porch, the front deck with Adirondack chairs, the fire pit in the backyard, and a wonderful sledding hill. Tesla EV Charger included.

The Big Lebearski

The Big Lebearski is a modern Killington home located just off the main road and close to everything. While you relax at our home after a day on the slopes, you can catch a movie on one of our smart TVs, relax in the outdoor hot tub, enjoy a drink by the cool motorcycle bar, shoot hoops in the game room or sit by the wood burning fire. This home is perfect for groups and families with lots of room to spread out and enjoy all that Killington has to offer.

two cabins

Dancing Bears – 2 Home Compound

Dancing Bears is a two home compound in the heart of Killington. Great location just off the access road, minutes to the slopes, walking distance to the market, restaurants and shuttle. Enjoy 2 homes on 2.7 gorgeous acres. Plenty of space for friends and family to connect and relax. Two hot tubs, 2 game rooms, 4 TVs, tons of indoor and outdoor space to make wonderful memories with friends and family. Enjoy 8 bedrooms with new luxurious linens, 4 baths and fully stocked kitchens.

FirBear – Newly Renovated

Revel in this bright, fully renovated (Nov 2021) modern ski condo just off Killington’s main road and close to everything. Relax after a day on the mountain streaming on one of your 3 smart TVs. Indulge with the fabulous condo amenities including the pool, hot tubs, spa, gym, and tennis courts, or settle in by the wood-burning fire. Spread out in this spacious condo and enjoy all that Killington has to offer.

CozyCub – Cheerful Mountain Haven

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington’s popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65″ TV. Enjoy the Whiffletree condo association’s outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

BearAll – Duplex on Killington Road

Reunite with friends and family in the heart of the Green Mountains with this rare opportunity to use both units of a duplex located on the main Killington access road, minutes from the resort base areas and everything the area has to offer!
With a patio as well as an upper deck with 2 grills in addition to a fire pit, you will have plenty of options to enjoy time with your group. Inside, you will have 6 smart Roku TVs and blazing-fast wifi!

BearLeft – 3BR Renovated by the Shuttle

Your group will be minutes from the slopes and everything else along the main Killington access road. This is the left unit of a duplex which has been lovingly renovated in a modern farmhouse style in 2022 to provide a wonderful stay and enhance your Vermont experience.
This house is perfect for a family or friends get-together for skiing, downhill mountain biking, Spartan racing, summer hiking leaf-peeping or even working remotely.

BearRight – Modern, Fire Pit, 3BR, Location

You will enjoy this beautiful, newly refreshed spot on the main access road in Killington, minutes from the slopes and everything the Heart of the Green Mountains has to offer. With a patio as well as an upper deck with grill in addition to a fire pit, you will have plenty of options to enjoy time with your group. Inside, you will have 3 smart Roku TVs and blazing-fast wifi!
You will have access to the right-hand unit of this beautiful duplex.

SugarBear – 2 BR / 2.5 Baths – Spacious, Airy

Forget your worries in this spacious and serene space. Close to everything Killington has to offer with all of the amenities of the Woods – Spa, Pool, Tennis, Hot Tub, Grill.

You’ll have exclusive access to the entire condo unit. You’ll walk in to the entrance with ample storage and into the soaring main living room with 2 story ceilings and loads of light. To the left is one King bedroom with a full en suite bath. Up the stairs to a second king bedroom with full en suite bath.

BearTrax – 3BR, Shuttle/Walk to Ski/Bike/Golf/Pool

You will be close to everything when you stay at this centrally-located place. Modern details and amenities combine with a classic alpine feel to create the perfect stay for your vacation. In the warmer months, enjoy the nearby Killington golf course or spend time with the family in the community pool. Located along the shuttle route, skiers and riders can arrive at base areas in minutes. At the end of a long day of adventures, curl up in front of the fireplace and enjoy the sunset views.

TheGrizz – 2BR Bike & shuttle on / off, on golf course

Mountain Green! Enjoy easy access to everything from this perfectly located home base right on the golf course. Located just off the Snowshed parking lot, Mountain Green Resort offers views, hiking, biking, relaxing and swimming at the pool.
This is a 2 bedroom condo with 1 full bath with tub / shower combo and one half bath. Stream your own channels on our Roku TV, play board games or try for a high score on the PacMan arcade system.

SnowCub – 2 BR + Loft | Fireplace, Pool, Hot Tub

Your group will be close to everything when you stay at this centrally-located condo. Enjoy two bedrooms plus a loft for a variety of sleeping options. Condo amenities include pool, gym, spa, tennis and hot tub. You will be close to the bars, restaurants, market and coffee shops and just minutes to the Killington resort base areas.

BearHaus – NEW 6BR, Huge Hot Tub

Nestled in the heart of Killington, this fully renovated and stylish home will welcome and delight your group. With two new kitchens, one focused on coffee and hot chocolate, the second a large kitchen with gorgeous table that can seat 16, your crew can enjoy time together or spread out and hang in the hot tub / bar area with a giant TV.

Killington Mountain Homes

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