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Featured Holiday Homes in Chittenden

Valley View Retreat is a tastefully decorated home.

Valley View Retreat is a tastefully decorated home.

Killington
With a stay at this vacation home in Killington, you'll be within a 10-minute drive of Pico Mountain at Killington Ski Resort and Killington Resort.
Valley View Retreat is a tastefully decorated home.
Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views

2 out of 5
Killington
With a stay at this vacation home in Killington, you'll be a 1-minute drive from Killington Resort and 6 minutes from Pico Mountain at Killington Ski ...
Walk to Pickle Barrel & Jax. Hot tub & Views
Killington, Vermont Ski House w/ Hot Tub and Sauna

Killington, Vermont Ski House w/ Hot Tub and Sauna

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, within a 10-minute drive of Pico Mountain at Killington Ski Resort and Killington ...
Killington, Vermont Ski House w/ Hot Tub and Sauna
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BruinsDen - Ski On Ski Off (Home Stretch Trail)

BruinsDen - Ski On Ski Off (Home Stretch Trail)

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 4-minute drive from Skye Peak Express ...
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Killington
With a stay at this vacation home in Killington, you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Plymouth
With a stay at this vacation home in Plymouth, you'll be within a 10-minute drive of Skyeship Express Gondola Stage I and Calvin Coolidge Homestead.
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, a 2-minute drive from Killington Resort and 8 minutes from Pico Mountain at Killington ...
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, within a 10-minute drive of Killington Resort and Pico Mountain at Killington ...
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

Killington
With a stay at this vacation home in Killington, you'll be a 1-minute drive from Killington Resort and 6 minutes from Skyeship Express Gondola Stage II.
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chittenden Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chittenden vacation homes are the perfect way for you to wing it.

Holiday houses in Chittenden let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chittenden in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chittenden adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chittenden with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chittenden vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chittenden Holiday Homes essential information

Accommodation
521 Holiday Homes
Lowest Price
AU$236
Highest Price
AU$568
Popular accommodation
Valley View Retreat is a tastefully decorated home., Walk to Pickle Barrel & Jax. Hot tub & Views, Killington, Vermont Ski House w/ Hot Tub and Sauna, BruinsDen - Ski On Ski Off (Home Stretch Trail), Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!, Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!, Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

Top trending hotels in Chittenden

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 out of 5
195 Mountain Top Road, Chittenden, VT
Fully refundableReserve now, pay when you stay
The price is AU$568 per night from 19 Jan to 20 Jan
AU$568
includes taxes & fees
19 Jan - 20 Jan
When you stay at The Mountain Top Inn & Resort in Chittenden, you'll be on a lake and steps from Green Mountain National Forest.
The Mountain Top Inn & Resort
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
The price is AU$236 per night from 12 Jan to 13 Jan
AU$236
includes taxes & fees
12 Jan - 13 Jan
With a stay at Comfort Inn Rutland - Killington in Rutland, you'll be 0.6 mi (1 km) from Rutland Regional Medical Center and 9.8 mi (15.7 km) from Pico Mountain ...
Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
The price is AU$349 per night from 14 Jan to 15 Jan
AU$349
includes taxes & fees
14 Jan - 15 Jan
With a stay at Killington Mountain Lodge, Tapestry Collection by Hilton in Killington, you'll be next to a golf course, just steps from Killington Resort and ...
Killington Mountain Lodge, Tapestry Collection by Hilton
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Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$237 per night from 9 Jan to 10 Jan
AU$237
includes taxes & fees
9 Jan - 10 Jan
When you stay at Days Inn by Wyndham Rutland/Killington Area in Rutland, you'll be near ski lifts, within a 5-minute drive of Vermont State Fairgrounds and Rutland ...
Days Inn by Wyndham Rutland/Killington Area
Don't see what you're looking for?
See all available properties in Chittenden
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.