Chittenden Vacation Packages 2026 from $809

Chittenden flight + hotel vacation packages

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

The Mountain Inn at Killington

$809

per person

Aug 13 - Aug 17

found 19 hours ago

Roundtrip non-stop flight included

Columbia (CAE) 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.

Four Columns Inn

$977

per person

Aug 13 - Aug 17

found 19 hours ago

Roundtrip non-stop flight included

Columbia (CAE) to Rutland (RUT)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A garden and a picnic area are also provided.

Killington Mountain Lodge, Tapestry Collection by Hilton

$821

per person

Aug 13 - Aug 17

found 19 hours ago

Roundtrip non-stop flight included

Columbia (CAE) to Rutland (RUT)

This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self parking, a terrace, and a lobby fireplace are also offered.

Castle Hill Resort And Spa

$1,084

per person

Aug 13 - Aug 17

found 18 hours ago

Roundtrip non-stop flight included

Columbia (CAE) to Rutland (RUT)

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and concierge services.

Emrose Luxury Cabins

$981

per person

Aug 13 - Aug 17

found 19 hours ago

Roundtrip non-stop flight included

Columbia (CAE) to Rutland (RUT)

This hotel's 8 hot tubs and sauna are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, barbecue grills, and wedding services are also on offer.

Top Chittenden hotels deals

The Mountain Top Inn & Resort

195 Mountain Top Road Chittenden VT

Free Cancellation

Reserve now, pay when you stay

$276 nightly

$301 total

Jun 8 - Jun 9

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

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$143 total

Jun 14 - Jun 15

Total with taxes and fees

Hot Tub

Pet friendly

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$469 nightly

$516 total

Jun 9 - Jun 10

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

Middlebury Inn

14 Court Square Middlebury VT

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$180 total

Jul 5 - Jul 6

Total with taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A business center, a terrace, and a lobby fireplace are also on offer.

Spa

Parking included

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$135 total

Jul 2 - Jul 3

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities are also on offer.

Pet friendly

Parking included

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$172 total

Jun 7 - Jun 8

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

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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.

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 $809. 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.