Chittenden Vacations from $505

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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.
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
Price was $559, price is now $505 per person
$505
per person
Jan 20 - Jan 22
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
8.8/10 Excellent! (1,002 reviews)
I liked the suite, very rustic and clean

Reviewed on Oct 23, 2025

Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Save 100% on your flight
Price was $5,032, price is now $4,096 per person
$4,096
per person
Dec 28 - Jan 1
found 13 hours ago
Roundtrip flight included
Baltimore (BWI) to Rutland (RUT)
No reviews
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $618, price is now $538 per person
$538
per person
Jan 20 - Jan 22
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9.2/10 Wonderful! (941 reviews)
The front desk staff are patient and enthusiastic.

Reviewed on Nov 24, 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 $906, price is now $812 per person
$812
per person
Jan 20 - Jan 22
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9/10 Wonderful! (53 reviews)
Arrived after dark. Didn’t know where to park. Very secluded. Outside light would not stay lit. Upstairs needs attention.

Reviewed on Oct 27, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $757, price is now $688 per person
$688
per person
Jan 20 - Jan 22
found 3 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
$295 nightly
The price is $322 total per night from Nov 29 to Nov 30
$322 total
Nov 29 - Nov 30
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
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (551 reviews)
Clean room, Awesome staff and always a good vibe.

Reviewed on Nov 17, 2025

Woodstock Inn & Resort
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
$116 nightly
The price is $128 total per night from Dec 10 to Dec 11
$128 total
Dec 10 - Dec 11
Total with taxes and fees
8/10 Very Good! (1,008 reviews)
The breakfast menu was a highlight. It was very exciting to see that there were waffle makers. Parking definitely felt safe, but it was not very easy. The room was clean. The staff was super friendly and helpful. There are snacks in the lobby. They have bubblers for regular water and lemon water ...

Reviewed on Nov 21, 2025

Comfort Inn Rutland - Killington
See all 1,899 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 $505 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.