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Essex Vacation Rentals

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Essex vacation rentals

Exterior

1. Dexter Victorian Homestead- Brand NEW Remodel April 2026. VERY Clean & Cozy

Dexter Victorian Homestead- Brand NEW Remodel April 2026. VERY Clean & Cozy
Dexter
8.0 out of 10, Very Good, (36 reviews)
"This was very convenient for our group - thank you!"
United States
Kathryn T.
$202 nightly
The price is $217
Sep 7 - Sep 8
Total with taxes and fees
Dexter Victorian Homestead- Brand NEW Remodel April 2026. VERY Clean & Cozy
Lobby

2. King Bed|Non-Smoking

King Bed|Non-Smoking
Malden MO
10.0 out of 10, Exceptional, (273 reviews)
"Appreciated how close this spot is to local attractions, made exploring so much easier than staying further away!"
United States
Anonymous traveler
$85 nightly
The price is $93
Sep 16 - Sep 17
Total with taxes and fees
King Bed|Non-Smoking
Private kitchen

3. The Cutie Patootie on Helen- Cute, Cozy, Comfortable - 3 BR Home in Dexter, MO

The Cutie Patootie on Helen- Cute, Cozy, Comfortable - 3 BR Home in Dexter, MO
Dexter
$150 nightly
The price is $161
Sep 7 - Sep 8
Total with taxes and fees
The Cutie Patootie on Helen- Cute, Cozy, Comfortable - 3 BR Home in Dexter, MO
Room

4. 2 Queen Beds|Non-Smoking

2 Queen Beds|Non-Smoking
Malden MO
10.0 out of 10, Exceptional, (187 reviews)
"Quick access from Takaroa Airport makes this an ideal stopover if you're traveling further!"
United States
Anonymous traveler
$94 nightly
The price is $103
Sep 16 - Sep 17
Total with taxes and fees
2 Queen Beds|Non-Smoking
Exterior

5. Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!

Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!
New Madrid
10.0 out of 10, Exceptional, (1 review)
"The host was very quick to respond and so great to work with for on our stay. "
United States
Jessica S.
$343 nightly
The price is $369
Sep 10 - Sep 11
Total with taxes and fees
Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!
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

Hampton Inn Sikeston

Hampton Inn Sikeston

10/10 Excellent
"This property was fantastic the moment we walked in the door. Been on the road for hrs and needed to stop. There was a room available at a great price. We were greeted by Brittany. She was so friendly and accommodating. She gave us complimentary water to take to our room. The room was so clean and fresh. The beds super comfortable. Thank you so much Brittany and staff for the warm welcome. We will always try to stay at a Hampton in the future! Thanks from Texas!"
Jennifer 1-night trip
Posted 5 hours ago
Hampton Inn Sikeston

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Essex in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $93 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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, we offer vacation rentals close to popular points of interest in Essex, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Essex?

Dexter Victorian Homestead- Brand NEW Remodel April 2026. VERY Clean & Cozy: This vacation home rental near Essex offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What’s there to see and do in Essex?

Explore the area and family-friendly sights such as Dexter Welcome Center Depot and Museum, or get out into nature at a spot like Central Park. Sikeston Depot Museum and The Heritage House are a couple of places you'll find in the larger area.

What’s a vacation rental in Essex like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Essex. Vacation rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.