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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was CA $782, price is now CA $697 per person
CA $697
per person
Nov 7 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.4/10 Exceptional! (809 reviews)
Room was clean and comfortable with lovely back deck overlooking the lake.

Reviewed on Aug. 12, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was CA $2,290, price is now CA $1,971 per person
CA $1,971
per person
Oct 8 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
For the price it's not to bad, slightly dated interior in need of a facelift, but would go back based on the price.

Reviewed on Aug. 10, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was CA $1,806, price is now CA $1,640 per person
CA $1,640
per person
Oct 8 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul. 23, 2025

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was CA $1,762, price is now CA $1,606 per person
CA $1,606
per person
Oct 8 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
9/10 Wonderful! (39 reviews)
We were able to have our amall dog with us.

Reviewed on Jul. 20, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was CA $1,569, price is now CA $1,440 per person
CA $1,440
per person
Oct 10 - Oct 14
found 12 hours ago
Roundtrip flight included
Saskatoon (YXE) to Rutland (RUT)
6.4/10 (1,004 reviews)
Clean and comfortable. Good value for what you get. Would stay again.

Reviewed on Aug. 18, 2025

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
The price is CA $449 per night from Aug 20 to Aug 21
CA $449
CA $489 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (86 reviews)
"The long view barn house was beautiful and well appointed."

Reviewed on Mar. 17, 2025

The Mountain Top Inn & Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $564 per night from Sep 1 to Sep 2
CA $564
CA $682 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul. 30, 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
The price is CA $211 per night from Aug 27 to Aug 28
CA $211
CA $246 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (803 reviews)
Get away to Vermont
"Nice get away spit in the country. Very clean and bed was comfortable. Fire pits were lite each night to sit out and enjoy. Short walk into town for shopping and eating. A market across the road was very convenient."

Reviewed on Aug. 14, 2025

The Shire Woodstock
See all 1,847 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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Frequently asked questions

How much does a Chittenden vacation package cost?
Offering excellent value package deals from CA $697 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.