Chittenden Vacations from $714

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Your Chittenden Vacation

The exciting city of Chittenden is calling your name. Delve into everything from its highlights to its hidden gems with a Chittenden vacation package that's custom made for you. Make your trip to Chittenden even more fun and exciting by going sightseeing. Appalachian Trail Adventures, Green Mountain National Golf Course and New England Maple Museum are some of the big attractions worth exploring. A few clicks is all it takes to create your perfect Chittenden vacation on Expedia.

The Latest Chittenden vacation packages

Price found within the past 48 hours. Click for updated prices.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $905, price is now $714 per person
$714
per person
Jan 24 - Jan 27
found 10 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9.2/10 Wonderful! (941 reviews)
Great place to stay!

Reviewed on Dec 2, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,685, price is now $1,209 per person
$1,209
per person
Feb 12 - Feb 15
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
No reviews
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,732, price is now $1,356 per person
$1,356
per person
Feb 12 - Feb 15
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
No reviews
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $933, price is now $739 per person
$739
per person
Feb 12 - Feb 15
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
9/10 Wonderful! (774 reviews)
Clean room, very nice staff, everything was excellent!

Reviewed on Dec 11, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,240, price is now $998 per person
$998
per person
Feb 12 - Feb 15
found 14 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared.

Reviewed on Nov 30, 2025

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Discover the most popular places to visit in Chittenden

Lefferts Pond

Explore the lovely green spaces of Lefferts Pond and enjoy the ski slopes in Chittenden. Discover the mountain views while you're in the area.

Lefferts Pond

Chittenden Hotel Deals

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
$325 nightly
The price is $354 total per night from Dec 12 to Dec 13
$354 total
Dec 12 - Dec 13
Total with taxes and fees
9/10 Wonderful! (95 reviews)
Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave.

Reviewed on Nov 19, 2025

The Mountain Top Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
$261 nightly
The price is $288 total per night from Dec 14 to Dec 15
$288 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (956 reviews)
We had a great weekend stay. Staff was great. We had a nice clean room, the continental breakfast had a great selection and the restaurant was really nice, food was delicious and so very convenient. We really enjoyed sitting by the fire in the lounge type room. And although we didnt bring our dog ...

Reviewed on Dec 5, 2025

The Mountain Inn at 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
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $206 total per night from Dec 14 to Dec 15
$206 total
Dec 14 - Dec 15
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
Clean room and bathroom. Alex at the desk was very helpful and nice.

Reviewed on Dec 5, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,921 properties in Chittenden
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.

Find the Best Chittenden Vacation Packages

Chittenden Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
1,250
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Pico Mountain at Killington Ski Resort, Killington Peak and Killington Adventure Center

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Frequently asked questions

How much does a Chittenden vacation package cost?
Offering great value package deals from $714 on Expedia, you'll be pleasantly surprised at how much a vacation to Chittenden costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chittenden?
You're likely to find lower prices and greater availability in April, May and June. Explore our cheap Chittenden vacation packages and you could score some excellent off-season deals.
How many days is enough for Chittenden?
Usually, a handful of days is enough to tick off the major sights during your Chittenden vacation. But if you prefer to have more time to rest or go on day trips, consider extending your itinerary.
How to find the best Chittenden package deals?
Use Expedia's handy filters to help you find some of the best Chittenden package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Chittenden package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chittenden vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Chittenden vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Chittenden?
If you're considering an impromptu Chittenden adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Chittenden vacation packages?
Your Chittenden break is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to allow you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.