Deals on vacations and trips to Chittenden

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Chittenden flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $905, price is now $714 per person
$714
per person
Jan 24 - Jan 27
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,685, price is now $1,209 per person
$1,209
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,732, price is now $1,356 per person
$1,356
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services and a virtual front desk are also provided.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $933, price is now $739 per person
$739
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
This resort features a restaurant, an indoor pool, and a bar/lounge. There's an outdoor tennis court on site, and a fireplace in the lobby and a picnic area are also provided.
Hidden Kingdom in Plymouth

Hidden Kingdom in Plymouth

2 out of 5
Save 100% on your flight
Price was $3,296, price is now $2,652 per person
$2,652
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Rutland (RUT)
This vacation home features laundry facilities. Take advantage of the free self parking.

Top Chittenden hotels deals

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 out of 5
195 Mountain Top Road Chittenden VT
Free Cancellation
Reserve now, pay when you stay
$325 nightly
The price is $354 total per night
$354 total
Dec 14 - Dec 15
Total with taxes and fees
This resort features a private beach, ski-in/ski-out access, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
On private beach
Pool
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Free Cancellation
Reserve now, pay when you stay
$261 nightly
The price is $288 total per night
$288 total
Dec 22 - Dec 23
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Free Cancellation
Reserve now, pay when you stay
$188 nightly
The price is $206 total per night
$206 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.
Hot Tub
Pet friendly
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$379 nightly
The price is $417 total per night
$417 total
Dec 15 - Dec 16
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
Pool
Hot Tub
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $176 total per night
$176 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $174 total per night
$174 total
Dec 18 - Dec 19
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Pet friendly
Parking included
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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.

Popular places to visit

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

Frequently asked questions

How much are vacation packages to Chittenden?
With Travelocity vacation packages, you can be living it up in Chittenden for as low as $714. Hotels, flights and adventures — we've got you covered. You'll save loads just by combining your bookings together. And with everything taken care of before you even set off, you can sit back, relax and enjoy the adventure.
How long should my Chittenden vacation be?
Typically, 4 nights is what many visitors book for their Chittenden trip. That's an useful guide, but there's so much more to uncover if you allow yourself a couple of extra days.
Where can I get the best vacation package deals for Chittenden?
You can snap up fantastic Chittenden package deals with Travelocity. Choose from as many as 400 airlines and 1,000,000 properties worldwide and turn your travel dreams into a reality.
Why should I purchase my Chittenden vacation package with Travelocity?
You'll not only enjoy big savings, but you'll also have access to our round-the-clock support, excellent service and a Price Match Guarantee. Explore every nook-and-cranny across the globe, uncover hidden treasures and make lifelong memories — we'll take care of the important details.
Can I save on my Chittenden car rental if I bundle it with a hotel or flight?
With a Chittenden vacation package, you can combine your flight, hotel and car bookings and save a ton. When you're ready to uncover the best of this impressive region, why not head to The Egg? This famous attraction is 85 mi from Chittenden. With a rental car, you'll be there soon enough.
Which airport is best for Chittenden?
For plenty of travelers, a stay in Chittenden means hopping off the plane at Burlington Intl. Airport (BTV). This bustling airport is situated 50 mi north of the downtown area. You could also fly into Lebanon Municipal Airport (LEB) (35 mi away from central Chittenden) or Rutland Southern Vermont Regional Airport (RUT) (14 mi away from central Chittenden).
What is there to do in Chittenden?
Lefferts Pond is one of the amazing sights that make Chittenden such a tourist hot spot. But allow yourself enough time to explore its lesser-known attractions too. This is sometimes where the best vacation memories are made.
Where should I stay when visiting Chittenden?
The The Mountain Top Inn & Resort is recommended by many visitors. Book now to avoid missing out.

Photos of local treasures

Browse Chittenden vacation photos for more inspiration