Chittenden Vacations from $459

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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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $622, price is now $459 per person
$459
per person
Jan 16 - Jan 19
found 1 hour ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9/10 Wonderful! (774 reviews)
Very welcoming, spacious, clean. Perfect for a family of 4.

Reviewed on Nov 18, 2025

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Save 100% on your flight
Price was $850, price is now $671 per person
$671
per person
Jan 16 - Jan 19
found 1 hour ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9/10 Wonderful! (1,000 reviews)
Beautiful Inn. Pretty, clean and well maintained. Close to Woodstock. Vt and shops. Highly recommend

Reviewed on Sep 30, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,242, price is now $1,019 per person
$1,019
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,679, price is now $1,403 per person
$1,403
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
No reviews
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,669, price is now $1,405 per person
$1,405
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
No reviews
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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 6 to Dec 7
$354 total
Dec 6 - Dec 7
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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$379 nightly
The price is $417 total per night from Dec 16 to Dec 17
$417 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (552 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on Nov 26, 2025

Woodstock 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 Dec 9 to Dec 10
$161 total
Dec 9 - Dec 10
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
If you want to travel to Killington with your pup, this is a great spot to stay! Right next to a golf course and other open space for dogs to run. Super friendly staff (Tahoe got lots of treats from the front desk). Great location. Good breakfast. Nice outdoor hot tub for a soak after hitting the ...

Reviewed on Dec 1, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,903 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 $459 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.