Chittenden Vacations from $628

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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.
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $760, price is now $628 per person
$628
per person
Jul 13 - Jul 17
found 12 hours ago
Roundtrip flight included
Orlando (ORL) to Rutland (RUT)
9/10 Wonderful! (1,001 reviews)
Wonderful staff and very charming inn!

Reviewed on Jun 4, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,035, price is now $890 per person
$890
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Very nice bed with comfortable mattress

Reviewed on Jun 9, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $793, price is now $688 per person
$688
per person
Jul 13 - Jul 17
found 12 hours ago
Roundtrip flight included
Orlando (ORL) to Rutland (RUT)
9.4/10 Exceptional! (936 reviews)
Everything at Bomoseen Lodge is very good. Convenient bar/ restaurant on the grounds. Lake is beautiful and fishing is great. Only complaint i could mention is the continental breakfast/ coffee doesn't open until 7:30am, so if your fishing early a.m., you miss out. Been staying here for years and it always opened earlier. Other than that, everything was great!

Reviewed on Jun 12, 2026

Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $868, price is now $765 per person
$765
per person
Jul 13 - Jul 17
found 12 hours ago
Roundtrip flight included
Orlando (ORL) to Rutland (RUT)
9/10 Wonderful! (118 reviews)
This was our second time staying here and it never disappoints! I booked this trip during our kids' spring break for a quick getaway and to use the amazing heated outdoor pool. It's a great location convenient to all the amazing sites Vermont has to offer. Would love to go back again in the fall!

Reviewed on Apr 19, 2026

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
Price was $1,028, price is now $910 per person
$910
per person
Sep 3 - Sep 7
found 22 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Rutland (RUT)
8.8/10 Excellent! (1,001 reviews)
Room was ok and the breakfast was ok. Nowhere handy for dinner. Ok for an overnight stop on route. Would find somewhere different next time.

Reviewed on Jun 10, 2026

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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
$269 nightly
The price is $293 total per night from Jun 24 to Jun 25
$293 total
Jun 24 - Jun 25
Total with taxes and fees
9/10 Wonderful! (120 reviews)
"Beautiful setting and views, perfect venue for events. Personable staff were superb. The event dinners were excellent. Many activities are available. Cons: Room decor was tired. The food menu choices are limited. Breakfast buffet for $20 is the only choice and food was not good both days we ate there. ..."

Reviewed on May 27, 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
$117 nightly
The price is $129 total per night from Jul 5 to Jul 6
$129 total
Jul 5 - Jul 6
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Very nice bed with comfortable mattress"

Reviewed on Jun 9, 2026

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

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$509 nightly
The price is $560 total per night from Jun 28 to Jun 29
$560 total
Jun 28 - Jun 29
Total with taxes and fees
9.4/10 Exceptional! (583 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Woodstock Inn & Resort
See all 1,966 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 $628 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.