Chittenden Vacation Packages

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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.

Top Chittenden Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Killington Haus

Killington Haus

2 out of 5
Price was CA $1,025, price is now CA $984 per person
CA $984
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9/10 Wonderful! (44 reviews)
Room were spotless , had actually what was advertised , it was self check in, everything was as expected!

Reviewed on Jul 1, 2026

The Landgrove

The Landgrove

3.5 out of 5
Price was CA $1,210, price is now CA $1,099 per person
CA $1,099
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
10/10 Exceptional! (1 review)
Tammy, the assistant inn keeper and restaurant manager was fantastic. She was attentive to every need. The restaurant staff was phenomenal as well highly recommend, it’s a little hidden gem off the beaten path. I will definitely return. Had a fabulous time.

Reviewed on Jun 27, 2026

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was CA $1,407, price is now CA $1,313 per person
CA $1,313
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9/10 Wonderful! (99 reviews)
The lock situation on the door to my cabin was concerning. The key was required to lock it from both the inside and the outside (presenting a hazard if I needed to escape quickly), and there was no deadbolt. There was another lock that had a keyhole on both the inside and outside, but my key did not work on it. As a single woman staying on the property entirely alone in the off season, I felt the need to barricade my door each night to ensure nobody could get in, since I couldn't deadbolt it.

Reviewed on Jun 18, 2026

The Vermont Inn

The Vermont Inn

3 out of 5
Price was CA $1,104, price is now CA $1,042 per person
CA $1,042
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9.2/10 Wonderful! (430 reviews)

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was CA $1,077, price is now CA $1,043 per person
CA $1,043
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
10/10 Exceptional! (1 review)

Ready to book your vacation to Chittenden?

 

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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
The price is CA $462 per night from Jul 8 to Jul 9
CA $462
CA $503 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (121 reviews)
"The room was spacious with beautiful view. Not much to do from activities perspective, beach was closed, kayak rentals were not open for the season. Breakfast was booked out due to Mothers Day weekend,"

Reviewed on Jun 26, 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
The price is CA $208 per night from Jul 12 to Jul 13
CA $208
CA $228 total
Jul 12 - Jul 13
includes taxes & fees
7.4/10 Good! (1,005 reviews)
"We had a great stay. The staff was nice and the property was awesome. The beds were super comfy and the rooms were clean.Close to everything."

Reviewed on Jul 5, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $659 per night from Jul 20 to Jul 21
CA $659
CA $787 total
Jul 20 - Jul 21
includes taxes & fees
9.4/10 Exceptional! (589 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 2026

Woodstock Inn & Resort
See all 1,953 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.
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Stay near popular Chittenden attractions

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.
See properties

Frequently asked questions

How much does a Chittenden vacation package cost?
Offering excellent value package deals from CA $984 on Expedia, you'll be thrilled with how little a vacation to Chittenden costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chittenden?
Plan your getaway for the low season and you're likely to score cheap Chittenden vacation packages. Remember that school vacation periods and local festivals and events can impact prices, so do a little research before booking.
How many days is enough for Chittenden?
The ideal length of your Chittenden vacation depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to visit all the main sights and discover some hidden spots along the way.
How to find the best Chittenden package deals?
Use Expedia's handy filters to help you find some fabulous Chittenden package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Chittenden package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early 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, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Chittenden vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Chittenden?
If you're planning a spur-of-the-moment Chittenden adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Chittenden?

  1. Choose when to get away: Check your schedule and get packing. Your preferred time of year and the type of activities available will also help you decide when to vacation in Chittenden.
  2. Budget wisely: In addition to the cost of your accommodations, you'll need to factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Chittenden.
  3. Decide how many days away: Start by compiling a list of the attractions you'd like to get to in Chittenden. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose a Chittenden vacation package that brings all your bookings together.

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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.