Chalet holiday rentals in Rutland County

4.84 out of 5 average rating, 264 reviews

Killington Chalet, Hot Tub, Sauna, Huge Boot Dryer

The Killington Chalet is your ideal vacation rental in the Green Mountains. It's the Right side of a duplex, perfect for families, couples, and groups. Located just off Killington Rd, it offers a secluded retreat near slopes, restaurants, and outdoor activities. Enjoy skiing, boarding, mountain biking, and more. Features include hot tub, sauna, boot dryer, wood stove, fire pit, and a fully equipped kitchen. Fresh linens, towels, and toiletries provided. Book for a memorable stay in every season!

FamilyLocationIndoor spaces

4.81 out of 5 average rating, 104 reviews

The exterior of a large chalet is showcased, featuring a steeply pitched roof and expansive windows. A wraparound deck provides access to the outdoors, surrounded by lush greenery. The structure exhibits a dark wood finish that contrasts with the clear blue sky.

Chalet in Granville

Hilltop Chalet | 360° Views · Theater · Gym · 6BR

Perched on a private hilltop on the NY/VT border with 360° views of rolling meadows. Sunsets and starry nights are spectacular. Soaring vaulted great room with catwalk, marble kitchen, master suite with jacuzzi, custom castle bunk beds, theater, game room (arcade, basketball, foosball), gym, central AC and fiber (250 Mbps). Outside enjoy a fire pit, bocce ball, and cornhole. Grocery store 5 minutes away. Lake George, Saratoga, Manchester VT and Killington all under an hour. 4WD req. in winter

LocationFamilyAccess

4.91 out of 5 average rating, 159 reviews

Chalet in Wells

Views! Entire Chalet, FAST Wi-Fi, All 18 Acres

June-August '26 special: 2 well-behaved pets stay for the rate of one - S'mores on us! Scenic, nearby lake, golf, hiking! Base rate includes up to 6 guests. Authentic Chalet is private, 3600 sqft, 18 acres, sleeps 13: 3 bedrooms, 1 King, 2 Queen, 3 Twin, 2 Queen sleeper-sofas, 3 full baths. Artisan fireplace, HVAC, oven, Induction cooktop, air fryer, ROKU HDTV, fast Wi-Fi, Fire Pit Patio. Linens/bath towels, soaps supplied. Add on: 5-star private studio/office. Events: reunions & weddings.

LocationFamilyCondition

5 out of 5 average rating, 63 reviews

Slippery Slope Chalet | 5 min to Base & Nightlife

Slippery Slope Chalet sits in the heart of Killington, just 5 minutes to the K1 Base Lodge and 2 minutes to the Access Road's restaurants, bars, and shops. Our rustic 4-bedroom, 2-bath retreat sleeps up to 8, ideal for families and groups: The house boasts a fully stocked gourmet farmhouse kitchen, open-concept living area, A covered hot tub, spa-like baths with rain showers and heated floors, an arcade room, and a 4-season sunroom for both lounging and gear storage with a boot and glove dryer.

FamilyLocationCondition

5 out of 5 average rating, 105 reviews

An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.

Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

🚲 15 MINUTES to KILLINGTON 🛀🏼 PRIVATE HOT TUB 🔥 OUTDOOR SAUNA 🎥 Outdoor MOVIE PROJECTOR 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🐕 PET FRIENDLY 🏌️‍♂️ 15 MINUTES to GOLF 🥾 Close to HIKING 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. See below! 👰🏻 < 20 minutes to MOUNTAINTOP 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens

ValueLocationTV

4.92 out of 5 average rating, 50 reviews

Chalet in Stockbridge

Private Mountain Sanctuary | 15 Min to Killington

This is not just a house. Welcome to your one-of-a-kind off-grid nature adventure! *NO Air conditioning. Most summer nights are cool and breezy, and we do have an industrial sized fan, but no AC due to off-grid solar set up. Wow: * Designer modern chalet on 150+ private acres of Vermont wilderness * Off-grid privacy with hiking trails, stargazing, complete seclusion * World-class mountain biking 5 minutes away. 360-degree panoramic views * Hike, Bike, Explore, Stargaze, Views Views Views!

LocationFamilyWi-Fi

A spacious wooden deck is featured, equipped with a large patio table and six chairs. A hot tub is positioned nearby, surrounded by trees. Large sliding doors offer access to the interior, allowing natural light to fill the space.

4.89 out of 5 average rating, 180 reviews

Kingsbrook: Chalet w Sauna, Hot Tub, AC!

Located off East Mountain Road, on a secluded dead end street, just minutes from your choice of the Killington base lodges. There is access to a ski/hiking trail at the end of our street (1/2 mile from the house), and we're surrounded by hiking and biking trails. The house is great for large groups and families, as there are 2 separate living areas (kids like to hang out in the lower family room with large screen TV and games). Very strong and fast internet. Now with AC for summer getaways!

ValueFamilyKitchen

4.98 out of 5 average rating, 124 reviews

The chalet is set against a backdrop of mountains and trees. The property features a large green lawn, and two dogs are seen resting on the grass in the foreground. The warm exterior of the home, complete with a deck, can be seen in the background.

Chalet in Wells

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

A beautiful chalet situated between mountains and Lake St Catherine. Whether on the deck or inside the house, you can enjoy the tranquil and serene view of the mountains and the lakes. At over 3000 sq ft, the house offers multiple gathering areas, including separate living room(s), a sociable kitchen, a pool table, and a bar. A perfect home for a retreat. Located less than 10 mins from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

LocationFamilyBiking

4.97 out of 5 average rating, 108 reviews

The Overlook - Views | Hot Tub | Fire Pits | Games

Escape to stunning mountain views at The Overlook. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

ValueLocationAccess

A two-story house is set amidst greenery, featuring a welcoming red door and a balcony with chairs. An American flag decorates the front, while gardening tools and vibrant flowers are arranged along the lower level. A grassy area surrounds the property.

4.92 out of 5 average rating, 204 reviews

Close to Mountain and easy walk to restaurants!

We have full weeks available upon request at a substantial discount. Killington Mtn is 1.4 miles away, so the Sports Park is an easy drive. The area offers skiing, snowboarding, tubing, hiking, biking, kayaking, ATVing, PLUS two excellent golf courses nearby. Restaurants and shops are walking distance. The house is casual and comfortable, located on a quiet dirt road with nice views of the valley from the upstairs and deck. There is a HOT TUB and SAUNA and linens included.

LocationValueCleanliness

4.95 out of 5 average rating, 129 reviews

A two-story chalet features a striking facade with dark wood framing and cream-colored walls. Snow covers the roof and ground, enhancing the winter ambiance. Yellow window shutters and stacked firewood are visible in front, providing a cozy, rustic touch to the scenic setting.

Chalet in Plymouth

Ledges Unit: Skyeship Gondola 2 miles w/ HOT TUB

The Ledges Unit is a recently updated home away from home just 2 miles from Killington’s Skyship Gondola. It is only 15 minutes from Killington’s main base area and 20 minutes to Okemo. The Ledges is a 2 story chalet in a 4 unit building. View sister listings by clicking my Host profile picture below. The 1st floor has a kitchen, living room with a large stone mantel and wood stove, dining room, and full bathroom. The 2nd floor has 4 bedrooms and bathroom.

LocationValueCleanliness