Chittenden Vacations from $1,194

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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.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,567, price is now $1,194 per person
$1,194
per person
Dec 20 - Dec 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
9/10 Wonderful! (57 reviews)
Thought of homesteading! It was a terrific little place and I could see staying a week. Fun. Clean. Pretty! I want one!

Reviewed on Oct 31, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,598, price is now $1,390 per person
$1,390
per person
Dec 20 - Dec 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
9.2/10 Wonderful! (410 reviews)
Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again.

Reviewed on Oct 23, 2025

Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $2,045, price is now $1,791 per person
$1,791
per person
Dec 20 - Dec 27
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
9.4/10 Exceptional! (628 reviews)
Hotel decor | Continental breakfast

Reviewed on Oct 25, 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
$295 nightly
The price is $322 total per night from Nov 5 to Nov 6
$322 total
Nov 5 - Nov 6
Total with taxes and fees
9/10 Wonderful! (93 reviews)
The inn is spectacular and the staff is great. The o Lu bad thing is that you can hear everything, including walking, in rooms above and next to yours in the inn. It would be great if the hotel made more of an effort to make guests aware of this so people can have a more restful stay.

Reviewed on Oct 10, 2025

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
$130 nightly
The price is $143 total per night from Nov 16 to Nov 17
$143 total
Nov 16 - Nov 17
Total with taxes and fees
7.2/10 Good! (1,001 reviews)
very nice place

Reviewed on Oct 22, 2025

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
$110 nightly
The price is $121 total per night from Nov 5 to Nov 6
$121 total
Nov 5 - Nov 6
Total with taxes and fees
8/10 Very Good! (1,013 reviews)
Quiet and low key.

Reviewed on Nov 2, 2025

Comfort Inn Rutland - Killington
See all 1,876 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 $1,194 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.