Chittenden Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chittenden

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 8.518.900 ₫ per night from 11 Aug to 12 Aug
8.518.900 ₫
10.678.507 ₫ total
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (86 reviews)
"The long view barn house was beautiful and well appointed."

Reviewed on 17 Mar 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 10.720.708 ₫ per night from 2 Sept to 3 Sept
10.720.708 ₫
12.946.107 ₫ total
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (530 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 30 Jul 2025

Woodstock Inn & Resort
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is 3.990.496 ₫ per night from 10 Aug to 11 Aug
3.990.496 ₫
4.389.546 ₫ total
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"This inn was great! I loved all the historical pieces that are shown around the inn. It is close enough to be able to walk to all the little shops and cafes in town. The staff were wonderful and super friendly. The food in the restaurant was amazing!"

Reviewed on 5 Aug 2025

Middlebury Inn
See all 1,859 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.

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 does a Chittenden holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Chittenden costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Chittenden?
Plan your trip for the off-peak season and you're likely to score cheap Chittenden holiday packages. Keep in mind that school holiday periods and major festivals and events can have an impact on prices, so do a little research before booking.
How many days is enough for Chittenden?
With a well-planned schedule, you can easily visit the top Chittenden sights in a few days. But if you prefer to discover hidden spots or take day trips, consider booking your Chittenden holiday for longer.
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 holiday package as soon as possible.
Is it cheaper to book a Chittenden holiday as a package?
Expedia holiday 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 personalised Chittenden holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Chittenden?

  1. Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the available activities will also help you decide when to escape to Chittenden.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to set aside for your trip to Chittenden. Then, select a hotel that works with your budget, whether that's an affordable stay or a high-end retreat.
  3. Decide how long to go away for: Now that you're up to speed on Chittenden, you can work out the ideal length of your break. Put together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your accommodation and airfare: Once you've settled on your dates and duration, lock in the ideal Chittenden holiday package for you.