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Essex Vacation Rentals

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Our top choices for Essex vacation rentals

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (222 reviews)
"Amazing stay, quiet, relaxing, will definitely do it again"
United States
Kelvin
The price is CA $192
CA $286 total
includes taxes & fees
Dec 13 - Dec 14
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is CA $440
CA $502 total
includes taxes & fees
Nov 20 - Nov 21
North Fork Resort

3. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $274
CA $471 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums

4. Groton Home < 1 Mi to Beach on Long Island Sound!

Groton Home < 1 Mi to Beach on Long Island Sound!
3.0 star property
Groton
The price is CA $563
CA $1,149 total
includes taxes & fees
Nov 22 - Nov 23
Groton Home < 1 Mi to Beach on Long Island Sound!
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.
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Top Essex Hotel Reviews

Find out more about Essex

Everything you need to know about Essex vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Essex vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Essex vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Essex vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Essex. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Essex vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Essex vacation rentals we have selected for you start as low as CA $286 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Essex rentals

At Expedia, we put the best Essex vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Essex rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Essex vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Essex. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there vacation rentals in Essex?

Yes, there are vacation rentals in Essex close to Essex Steam Train, or you can go with a more remote option if you're looking for a relaxing stay. Our travelers say Essex has a good selection of bars. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best vacation home rentals in Essex?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental near Essex is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Essex?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Essex stay.

What’s there to see and do in Essex?

Family-friendly attractions include Essex Steam Train and Sweet Martha's, whereas Connecticut River is a spot to enjoy the outdoors. Essex Island Marina and Essex Library are other places to visit while you're in town.

What’s a vacation rental in Essex like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Essex. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for families.