Cheap Flights to Essex County (2026/2027)

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Best Essex County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Essex House and Tavern
2.0-star property

Essex House and Tavern

Oct 7 - Oct 10

3 night stay

Chicago (CHI) to Whitefield (HIE)

United • Roundtrip • Coach
Price was $618, price is now $530 per person
$530
per person
found 1 day ago
Island Pond Country Inn (Formerly the Lakefront Inn & Motel)
2.0-star property

Island Pond Country Inn (Formerly the Lakefront Inn & Motel)

Oct 1 - Oct 5

4 night stay

Dallas (DFW) to Whitefield (HIE)

United • Non-stop roundtrip • Coach
Price was $1,043, price is now $944 per person
$944
per person
found 1 day ago
The Inn at OxBow Acres
3.5-star property

The Inn at OxBow Acres

Sep 18 - Sep 21

3 night stay

New York (JFK) to Whitefield (HIE)

JetBlue Airways • Roundtrip • Coach
Price was $743, price is now $677 per person
$677
per person
found 19 hours ago
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Travelers ❤️ These Essex County 🏨

Island Pond Country Inn (Formerly the Lakefront Inn & Motel)

Island Pond Country Inn (Formerly the Lakefront Inn & Motel)

2 out of 5
127 Cross St Brighton VT
Stay at this motel in Brighton. Enjoy free WiFi, free parking, and housekeeping. Popular attractions Island Pond Historical Society Museum and Island Pond Public Library are located nearby.
Opens in a new windowIsland Pond Country Inn (Formerly the Lakefront Inn & Motel)
Essex House and Tavern

Essex House and Tavern

2 out of 5
138 Cross Street Island Pond VT
Stay at this hotel in Brighton. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Island Pond Historical Society Museum and Island Pond Public Library are located nearby.
9/10 Wonderful! (24 reviews)
"Decent little hotel. Town was a bit weird. Yellow deli had great food but you should read about what it is before you go!"

Reviewed on Sep 3, 2026

Opens in a new windowEssex House and Tavern
Omni Mount Washington Resort & Spa

Omni Mount Washington Resort & Spa

4 out of 5
310 Mt Washington Hotel Rd Bretton Woods NH
Book a stay at this luxury resort in Bretton Woods. Enjoy free WiFi, a full-service spa, and 9 restaurants. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Bretton Woods Ski Area and Mount Washington Cog Railway are located nearby.
Opens in a new windowOmni Mount Washington Resort & Spa
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Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
101 Mountain View Rd Whitefield NH
Book a stay at this spa hotel in Whitefield. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Santa's Village and Weathervane Theatre are located nearby.
8.8/10 Excellent! (1,001 reviews)
"Beautiful resort. Lovely grounds and landscaping. Some of the area were closed off. Pool area was nice but there was no food or drinks nearby. The building next to the pool area was mostly shutdown."

Reviewed on Sep 9, 2026

Opens in a new windowMountain View Grand Resort & Spa
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.

Frequently asked questions

How much is the cheapest flight to Essex County?
To give you an idea of fares, the cheapest roundtrip flight to Essex County was in the last seven days. An excellent way to snap up a good deal is to be flexible with your dates. This price was available on Travelocity for flights to Essex County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Essex County?
There are airline companies that fly to Essex County. If you're planning a trip to Warner's Grant, choose American Airlines. This popular carrier operates roughly 342 flights per month to Essex County's primary city.
What is the cheapest month to fly to Essex County?
Based on Travelocity's direct return flight demand between January and December last year, is the cheapest time to jet off to Essex County. Keep an eye out for flights during this month and bag yourself a terrific bargain today.
How can I check my flight status to Essex County?
"Trips" will clue you in when it comes to details about your flight to Essex County. Our handy portal lets you organize everything in the one place, from checking the status of your flight to making changes to your booking. Click on Trips at the top right of the Travelocity homepage and then create a free account in seconds. Alternatively, download the Travelocity app and access your itinerary while you're on the move. Whether you have the family flying with you or you're a solitary wanderer, all your travel plans are at your fingertips.
How do I find the best deals on flights to Essex County?
Be flexible with your dates and there's a good chance you'll find a sensational deal. When searching for flights on Travelocity, click the "Flexible dates" feature at the top of the page to see all the prices for surrounding days. Also try to book well in advance and avoid peak periods. In the last seven days, the lowest price for a roundtrip flight to Essex County was . This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Essex County with Travelocity?
Where to begin! With cheap flights to Essex County, accommodations and activities, you'll find all you need to create your ideal trip with Travelocity. Reserve your cheap family flights and take advantage of our round-the-clock customer support and Price Match Guarantee if you need. Our goal is to offer stress-free travel every time you book with us so that you can spend less time worrying and more time having fun with your travel buddies.
What are the most popular flight routes to Essex County?
Whether you're thinking about a short trip or a lengthy vacation, we can help you book your perfect flight to Essex County. The top flight routes to this destination include:

  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 949 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Portland Intl. Jetport Airport (PWM) - 676 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Portland Intl. Jetport Airport (PWM) - 645 flights a month.

How much is a flight to Essex County on average?
Airfares for roundtrip flights to Essex County were priced between and in the last seven days. As soon as you see an incredible deal, lock it in and get ready to take off on your next epic adventure with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Essex County?
To get an idea of the average duration of a direct flight to Essex County, cast your eyes over these in-demand routes:

  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 20 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Portland Intl. Jetport Airport (PWM) - 2 hours and 21 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 32 minutes

What can I expect on a flight to Essex County?
This will mostly depend on where you're taking off from and which airline you're flying with. You're likely to find all kinds of flights to Essex County, from business fares to cheap flights for family vacations. On long-haul flights, your carrier will typically offer meals and drinks, a range of entertainment programs as well as games to keep the kids happy.