Chittenden Vacations from $728

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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.
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
Price was $752, price is now $728 per person
$728
per person
Sep 30 - Oct 2
found 9 hours ago
Roundtrip flight included
Los Angeles (QLA) to Rutland (RUT)
8/10 Very Good! (1,003 reviews)
Comfortable and convenient. Good value for the money.

Reviewed on Aug 22, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $989, price is now $917 per person
$917
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, even just donuts.

Reviewed on Aug 22, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $786, price is now $743 per person
$743
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $891, price is now $859 per person
$859
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
9.2/10 Wonderful! (869 reviews)
The hotel is very nice, very friendly, beautiful views specially from the room with balcony. Game room is awesome and the breakfast was delicious. Will come back again.

Reviewed on Aug 20, 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $1,011, price is now $978 per person
$978
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
9/10 Wonderful! (47 reviews)
We booked a non-smoking room. Showed up and the place ABSOLUTELY reaked of smoke. The smell was caked into everything including bedding. It was like they were smoking 10 packs plus a day and didn’t leave. Lamps and cabinets were broken as well. Cleaners also showed up at 6am blasting music, which was well before the 11am check out of the property. owners of the property did communicate well and that was much appreciated. However after this stay we are still feeling sub par out this place.

Reviewed on Aug 4, 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 Aug 24 to Aug 25
$354 total
Aug 24 - Aug 25
Total with taxes and fees
9/10 Wonderful! (87 reviews)
"The long view barn house was beautiful and well appointed."

Reviewed on Mar 17, 2025

The Mountain Top Inn & Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night from Sep 1 to Sep 2
$494 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Woodstock Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $139 total per night from Aug 24 to Aug 25
$139 total
Aug 24 - Aug 25
Total with taxes and fees
9/10 Wonderful! (872 reviews)
"The hotel is very nice, very friendly, beautiful views specially from the room with balcony. Game room is awesome and the breakfast was delicious. Will come back again."

Reviewed on Aug 20, 2025

The Mountain Inn at Killington
See all 1,852 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.

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Frequently asked questions

How much does a Chittenden vacation package cost?
Offering great value package deals from $728 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.