Essex Vacations from $404

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Your Essex Vacation

From its highlights to its hidden gems, this city is best explored with a Essex vacation package. Book a hotel in Essex Village, which is good for walking, hiking and views. Like to venture out and explore? Essex Steam Train, Gillette Castle State Park and Goose Island are just a few of the top places to visit during your trip to Essex. Expedia will help you escape the everyday. Tailor your vacation to Essex to suit your travel style, whatever that may be!

The Latest Essex vacation packages

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

$404
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.4/10 Very Good! (1,133 reviews)
Convenient location close to the airport. Staff friendly and kind providing good service. Room with appliances, and all you need from a kitchen. Quiet, clean, and comfy.

Reviewed on Sep 29, 2026

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

$459
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (1,003 reviews)
The room was clean, comfortable bed and our needs were met. The kids enjoyed the pool located downstairs

Reviewed on Sep 29, 2026

Inn at Middletown

Inn at Middletown

Washington Street Historic District
$998
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
9/10 Wonderful! (651 reviews)
Great hotel! Had a lot of character to it. Staff were great and the tavern at the property was great too.

Reviewed on Sep 26, 2026

The Cromwell Inn

The Cromwell Inn

$434
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
7.2/10 Good! (17 reviews)
We were very pleased with this hotel. Great price. They are in the process of remodeling the hotel and our room was vey nice & updated. They staff was friendly & helpful. The breakfast was a bit disappointing as small selection. We had to leave a $100 cash deposit which was promptly returned to us when checking out. Overall this was a nice stay.

Reviewed on Sep 29, 2026

Courtyard by Marriott Hartford Cromwell

Courtyard by Marriott Hartford Cromwell

$581
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (761 reviews)
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Stay near popular Essex attractions

A steam locomotive with the number 40 on its front, traveling on a railway track.
Photo by Bill Dillard

Essex Steam Train

8.4/10 (165 reviews)
Travel back in time aboard the Essex Steam Train's 1920s Pullman coaches through the Connecticut River Valley. This journey combines vintage rail travel with a scenic riverboat cruise.
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The Beverly Public Library with a grand entrance, steps, and a clear blue sky.

Essex Library

7.6/10 (21 reviews)
The Essex Library serves as a vibrant community hub with diverse collections and educational programs for all ages. Browse the local history section or attend author talks and cultural events.
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A historic building with a balcony and a sign reading "Connecticut River Museum".
Photo by Bill Dillard

Connecticut River Museum

10.0/10 (3 reviews)
Explore maritime heritage in this riverside museum in an 1878 Steamboat Dock building. Climb aboard the Turtle submarine replica or take a seasonal river cruise to experience Connecticut's aquatic history firsthand.
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Pratt House

Built in 1803, the Pratt House showcases classic Colonial architecture with its stone foundation and wooden siding. Admire the exterior and gardens before exploring the charming shops and galleries of Essex Village.
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Hattitudes

Enjoy an outing to Hattitudes during your stay in Essex Village. While you're in the area, stroll along the beautiful beaches.
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Sweet Martha's

Enjoy an outing to Sweet Martha's during your stay in Essex Village. While you're in the area, stroll along the beautiful beaches.
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Essex Hotel Deals

Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

269 North Frontage Road New London CT
Fully refundableReserve now, pay when you stay
$100 nightly
$115 total
Oct 1 - Oct 2
Total with taxes and fees
6/10 (1,007 reviews)
"This was kind of an interesting property with lots of attached and detached buildings making up the total. All of the outer doors looked like they had new electric locks installed but the new mechanisms left huge unfilled holes in the door frames. While the pool was open, the lights were off, and ..."

Reviewed on Sep 27, 2026

Regency Inn & Suites New London, Mystic
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$78 nightly
$90 total
Oct 7 - Oct 8
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex
Mystic Marriott Hotel and Spa

Mystic Marriott Hotel and Spa

625 North Rd Groton CT
$167 nightly
$192 total
Oct 18 - Oct 19
Total with taxes and fees
Mystic Marriott Hotel and Spa
See all 1,462 properties in Essex
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 Essex Vacation Packages

Things to do near Essex

Essex, Connecticut, offers a charming mix of outdoor and romantic activities perfect for a scenic getaway. Enjoy a round of golf at local courses, explore recreational areas, or relax at nearby resorts. Don't miss the iconic Essex Steam Train and the Essex County Holiday House Tour for a taste of local history. For family fun, head to amusement parks or Adventure Island, and take part in guided house tours to soak in the area's unique charm.

Shopping

In Essex, visit the Essex Plaza Shopping Center, just 1 mile away, for a family-friendly atmosphere. The Essex Saybrook Antique Village Shopping Center, located 3 miles away, offers unique finds. If you're up for a drive, the Clinton Crossing Premium Outlets, 9 miles from Essex, features numerous brand-name stores.

Recreation

Enjoy a refreshing swim at Ocean Beach Park, where family-friendly vibes and outdoor sports await just 16 miles away. Experience culture and romance at the Ivoryton Playhouse, located 3 miles from Essex, or hit the greens at Cedar Ridge Golf Course for a perfect day outdoors, only 9 miles away.

Adventure

At Stay and Play LLC, located 5 miles from Essex, enjoy an exciting arcadeAdventureZone filled with family-friendly games. For thrill-seekers, head to Waterford Speedbowl, 12 miles away, where you can experience exhilarating motorRacing action. Kids Quest, an arcadeAdventureZone 18 miles from Essex, offers fun for the whole family.

Nightlife

In Essex, Connecticut, enjoy a cozy nightlife featuring local bars and restaurants like The Griswold Inn and The Essex Steam Train. Experience live music and vibrant atmospheres along Main Street, where friendly locals create an inviting ambiance perfect for winding down after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Essex

Essex, Connecticut, is a charming destination perfect for outdoor and romantic getaways. Visitors can explore scenic spots like the Essex River, the quaint Essex Village, and the fascinating Essex Shipbuilding Museum. With attractions that include beautiful beaches, historic houses, and nearby state parks, Essex offers a delightful mix of adventure and relaxation, making it an ideal destination for those seeking a picturesque escape.

  • Essex Steam Train: Experience the charm of a bygone era on the Essex Steam Train, where you can ride vintage steam locomotives through beautiful Connecticut scenery. Explore the railway museum and immerse yourself in the rich cultural history of rail travel in America.
  • Essex Island Marina: Dive into outdoor adventures at Essex Island Marina, offering access to picturesque beaches and water activities. Rent a kayak, go fishing, or simply relax by the water while soaking in the vibrant atmosphere of this stunning marina.
  • Gillette Castle State Park: Just a short drive from Essex, Gillette Castle State Park features breathtaking views and hiking trails. Explore the unique castle built by actor William Gillette, surrounded by scenic landscapes perfect for outdoor enthusiasts.

Best time to go to Essex

The best time to visit Essex is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowSlightly Low
February32.4°F (0.2°C)Light RainMostly SunnySlightly LowAverage
March38.5°F (3.6°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnyAverageSlightly High
July73.8°F (23.2°C)Light RainMostly SunnySlightly HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
September66.2°F (19.0°C)Light RainMostly SunnySlightly HighAverage
October56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
November45.5°F (7.5°C)Light RainMostly SunnyAverageAverage
December37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Essex

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Essex.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Essex Essential Information

Language
English
Currency
U.S dollars
Population
2,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Harveys Beach, Goodspeed Opera House and Devils Hopyard State Park

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Frequently asked questions

How much does an Essex vacation package cost?
You'll find cheap prices from $404 on Expedia for your Essex getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Essex costs.
What are the cheapest months to go to Essex?
You're likely to find reduced prices and better availability in December, January and February. Check out our cheap Essex vacation packages and you could land some great off-season discounts.
How many days is enough for Essex?
To fully enjoy your Essex vacation, we recommend staying for 2 days. Divide your time between discovering Essex Island Marina, Pratt House and other leading sights, on top of experiencing neighborhoods like Old Saybrook Center and Lyme. If you've got some spare time, include a day trip in your Essex vacation itinerary.
Is it worth booking a vacation package to Essex?
It's no wonder an Essex vacation is on the must-do list of many travelers. Popular attractions like Essex Steam Train are just the beginning of what you can explore here.
How to find the best Essex package deals?
Finding a cheap Essex package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, add a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Essex package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Essex vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Essex getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Essex?
If you have your Essex vacation dates confirmed, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Essex vacation packages?
Your Essex break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you extra 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 are no late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.