Luxury Vacation Rentals for Families in Killington

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 8 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Killington

Chalet 91 at Killington

4 bedrooms•3.5 baths

New

Mountain Green 3A7

2 bedrooms•2 baths

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New

~$55 less than other sites

The Mountainside House

5 bedrooms•6.5 baths

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New

~$570 less than other sites

Fun In Fun Out Ski Home - Both

6 bedrooms•4 baths

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New

~$135 less than other sites

The Matterhorn House

4 bedrooms•3 baths

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New

~$155 less than other sites

Trailside Village 6

3 bedrooms•2 baths

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New

~$180 less than other sites

Peak Hill Home

3 bedrooms•2 baths

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New

~$75 less than other sites

Vistas 92

4 bedrooms•4.5 baths

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New

~$235 less than other sites

Welcome to family adventures in Killington

Bring everyone together in Wander’s luxury family vacation rentals in Killington, Vermont. Our handpicked mountain homes pair the polish of a five-star hotel with the space and privacy families need, so coordinating grandparents, toddlers, and teens feels effortless.

Expect multi-bedroom layouts, kid-friendly sleeping options, and generous living areas designed for downtime. With chef-ready kitchens, smart entertainment, ultra fast WiFi, pristine cleaning, and 24/7 concierge, home life runs smoothly. Many homes add decks, game nooks, or soothing hot tubs, giving every generation room to relax. Dedicated workspaces keep parents on schedule while kids spread out to play.

Available soon in Killington

The Mountainside House

5 bedrooms•6.5 baths

•

New

~$570 less than other sites

The Matterhorn House

4 bedrooms•3 baths

•

New

~$155 less than other sites

Vistas 92

4 bedrooms•4.5 baths

•

New

~$235 less than other sites

Featured family vacation rentals in Killington

The Mountainside House

5 bedrooms•6.5 baths

•

New

~$570 less than other sites

Vistas 92

4 bedrooms•4.5 baths

•

New

~$235 less than other sites

Highlights in Killington

Discover a mountain playground packed with family-friendly ski slopes, thrilling alpine coasters, and scenic, easy-to-explore nature trails.

Killington Adventure Center

Thundering Brook Falls Trail

Gifford Woods State Park

Kent Pond

Pico Mountain Ski Resort

President Calvin Coolidge State Historic Site

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Killington

Chalet 91 at Killington

4 bedrooms•3.5 baths

New

Mountain Green 3A7

2 bedrooms•2 baths

•

New

~$55 less than other sites

The Mountainside House

5 bedrooms•6.5 baths

•

New

~$570 less than other sites

Fun In Fun Out Ski Home - Both

6 bedrooms•4 baths

•

New

~$135 less than other sites

The Matterhorn House

4 bedrooms•3 baths

•

New

~$155 less than other sites

Trailside Village 6

3 bedrooms•2 baths

•

New

~$180 less than other sites

Peak Hill Home

3 bedrooms•2 baths

•

New

~$75 less than other sites

Vistas 92

4 bedrooms•4.5 baths

•

New

~$235 less than other sites

View all homes

Most popular amenities for family vacation rentals in Killington

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Private pool vacation rentals in Killington

Discover more family fun in Killington

Set in Vermont’s Green Mountains, Killington delivers four distinct seasons to share with the whole crew. Winter brings soft corduroy mornings and gentle learning zones, while summer reveals lift-served views, family-friendly trails, swimming spots, and misty waterfalls. When autumn arrives, ridge lines blaze with color for scenic drives and easy walks that wow without the crowds.

Beyond the main peak, explore nearby Pico, stroll boardwalk paths to cascades, and plan simple day trips to postcard towns like Woodstock and Quechee Gorge. Farm stands, markets, and local makers turn picnics into a treat. This is why Wander’s luxury family vacation rentals in Killington, Vermont are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Killington

Why should I book a Wander in Killington over other family vacation rentals?

Wander offers a level of consistency and quality you won’t find with most family vacation rentals.

Every home in Killington delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular family vacation rentals in Killington?

Some of our most popular family vacation rentals in Killington include Chalet 91 at Killington, Mountain Green 3A7, and The Mountainside House. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different family vacation rentals does Wander have available in Killington?

Wander offers 8 family vacation rentals in Killington, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s family vacation rentals in Killington?

You can check-in to Wander family vacation rentals in Killington after 4.00pm and check-out before 10.00am.

Do Wander’s family vacation rentals in Killington have WiFi access?

Yes. Every Wander home in Killington has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.