Chittenden Vacations from $532

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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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $635, price is now $532 per person
$532
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Syracuse (SYR) to Rutland (RUT)
9.4/10 Exceptional! (930 reviews)
Beautiful and comfortable room with a fantastic view of the lake. The free use of canoes and kayaks onsite was a pleasant surprise!

Reviewed on May 25, 2026

Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Price was $715, price is now $566 per person
$566
per person
Jun 27 - Jun 30
found 5 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
10/10 Exceptional! (44 reviews)
We stayed for the weekend and went skiing at Okemo. It was a 10 min drive away. The staff was very accommodating, welcoming and friendly. The food provided was delicious. We will definitely be back!

Reviewed on Mar 8, 2026

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $739, price is now $621 per person
$621
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
No reviews
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $933, price is now $784 per person
$784
per person
Aug 1 - Aug 6
found 13 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Rutland (RUT)
9.2/10 Wonderful! (1,006 reviews)
We had a fantastic time at the Mountain Inn. I was there for a 100 mile race and the staff went above and beyond to ensure I had everything I needed to be successful. They even went to the trouble to make me my own breakfast to go! We will absolutely be back to see JP and Bodie!

Reviewed on May 24, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $993, price is now $837 per person
$837
per person
Aug 1 - Aug 6
found 13 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Rutland (RUT)
8.8/10 Excellent! (1,005 reviews)
Another great stay. The hot pool is rad. It is super mega to have the bar and restaurant on-site! Staff are always friendly and helpful.

Reviewed on Apr 27, 2026

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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
$276 nightly
The price is $301 total per night from Jun 1 to Jun 2
$301 total
Jun 1 - Jun 2
Total with taxes and fees
9/10 Wonderful! (119 reviews)
"The grounds are beautiful. The room was lovely. We did have an issue with the thermostat and controlling the temperature. Our greatest issue was the fact that even with the resort Wi-Fi connected and the password put in, the service was so poor that the phone wouldn’t work from one second to the ..."

Reviewed on May 15, 2026

The Mountain Top Inn & Resort
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
$147 nightly
The price is $161 total per night from Jun 11 to Jun 12
$161 total
Jun 11 - Jun 12
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Place is beautiful well kept rooms are clean nice sized. My only “complaint” was hot tub area which is fabulous opens at 10am, and we were leaving that day at 9. But that was a very minor inconvenience I will be back next year for sure!"

Reviewed on May 15, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from Jun 21 to Jun 22
$149 total
Jun 21 - Jun 22
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
"Free parking, clean room."

Reviewed on May 25, 2026

Comfort Inn Rutland - Killington
See all 1,969 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 $532 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.