Chittenden Vacations from $797

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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.
Golden Stage Inn B&B

Golden Stage Inn B&B

$797
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
10/10 Exceptional! (45 reviews)
Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!

Reviewed on Jul 6, 2026

Mountain Green Resort

Mountain Green Resort

$1,610
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

The Suites at Killington Center

The Suites at Killington Center

$1,473
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
No reviews
The Vermont Inn

The Vermont Inn

$1,274
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Rutland (RUT)
9.2/10 Wonderful! (431 reviews)
The place needs a little help. The room was cute but one of the sinks needed cleaning and there was No coffee creamer and the place needs tlc. A little disappointed but I get it

Reviewed on Aug 8, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

$1,076
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9/10 Wonderful! (865 reviews)
There was a lot to love about Holiday Inn Club Vacations Mount Ascutney, especially for a larger family or group. Our three-bedroom villa was BY FAR the largest accommodation of our trip and surprisingly affordable. We had tons of room to spread out, a decent-sized kitchen for cooking, and FREE laundry—a huge win during a long road trip! The villa kitchen was helpful but pretty minimally stocked. Cooking utensils and cutting boards were lacking, so bring some basics if you plan to cook. Grills are available, but you’ll need charcoal. I’d recommend buying it and any groceries before arriving because the onsite marketplace is expensive. The biggest disappointment was the pool, which is closed through 2027. Traveling with kids, that was a major bummer and definitely something families should know before booking. The location is incredibly beautiful, tucked away on a Vermont mountainside, but it is truly in the middle of nowhere. Come prepared! Overall, the incredible amount of space and affordability made it work really well for our group. It wasn’t our favorite stay of the trip, but the value for a three-bedroom villa was hard to beat.

Reviewed on Aug 30, 2026

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Stay near popular Chittenden attractions

Lefferts Pond

Tucked within Vermont's Green Mountain National Forest, Lefferts Pond offers 55 acres of motorboat-free tranquility. Kayak while watching for moose, otters, and warblers in this peaceful wilderness retreat.
See properties

Chittenden Hotel Deals

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

195 Mountain Top Road Chittenden VT
$276 nightly
$301 total
Sep 2 - Sep 3
Total with taxes and fees
9/10 Wonderful! (122 reviews)
"Beautiful relaxed setting. Gorgeous views. Perfect combination of activities vs. simply relaxing. My only complaint was that the restaurant menu was somewhat limiting. It would have been nice to have more varied options and more vegetarian options for lunch vs. dinner"

Reviewed on Aug 26, 2026

The Mountain Top Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

47 Old Mill Rd Killington VT
$124 nightly
$136 total
Sep 2 - Sep 3
Total with taxes and fees
The Mountain Inn at Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green Woodstock VT
$388 nightly
$426 total
Sep 7 - Sep 8
Total with taxes and fees
Woodstock Inn & Resort
See all 1,957 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 $797 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.