Discover Your Perfect Essex Vacation Homes

Why Choose Rent By Owner for your Essex Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Essex

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here can enhance your experience, as this destination offers distinct advantages during different seasons in Essex, Connecticut, USA.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences warm weather that is ideal for outdoor activities and exploring the scenic coastline.

Average Temperature Daytime: around 75°F to 85°F - Nighttime: about 60°F to 65°F
autumn
Fall (September to November)

Early fall offers pleasant temperatures and vibrant foliage, making it a popular time for visitors seeking picturesque views and comfortable weather.

Average Temperature Daytime: approximately 70°F to 75°F - Nighttime: around 50°F to 55°F

Off-Season Highlights

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Late Winter (January to February)

This period sees fewer visitors, with cooler temperatures that are perfect for those who enjoy peaceful escapes and cozy accommodations.

Average Temperature Daytime: roughly 40°F to 45°F - Nighttime: about 25°F to 30°F
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Early Spring (March to April)

Before the full bloom of spring, the region offers quieter surroundings and moderate weather suitable for exploring without the crowds.

Average Temperature Daytime: around 50°F to 55°F - Nighttime: approximately 35°F to 40°F

Weekly Weather Forecast for Essex

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or deck perfect for relaxing and entertaining in the fresh air.
  • Take advantage of spacious yards ideal for outdoor activities or family gatherings.
  • Make use of a barbecue grill to host cookouts while soaking up the regional sunshine.
  • Relax by a cozy outdoor fire pit on cooler evenings, creating a warm and inviting atmosphere.
  • Explore well-maintained gardens or landscaped areas that showcase the area's natural beauty.
  • Utilize outdoor dining spaces to enjoy meals with scenic views of the surrounding region.
  • Access to nearby water features such as docks or waterfronts for fishing, boating, or sightseeing.
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Family Activities

  • Essex River Museum: Explore maritime history through interactive exhibits and engaging displays that the whole family can enjoy here in the region.
  • Deep River Landing: Spend a relaxing day by the water, kayaking, picnicking, or simply unwinding along the scenic shoreline of this popular spot.
  • Essex Steam Train & Riverboat: Experience a nostalgic journey aboard historic steam engines combined with a river cruise, offering memorable adventures for families visiting here.
  • Connecticut River Estuary Kayaking: Discover the local natural beauty with guided kayaking tours along the estuary, perfect for outdoor enthusiasts in this area.
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Adult Activities

  • Essex River Cruises: Experience the scenic beauty of the area’s waterways with a relaxing cruise that offers stunning views and insight into the region's maritime heritage.
  • Connecticut River Museum: Discover the history and ecology of the Connecticut River through engaging exhibits and interactive displays, perfect for gaining a deeper understanding of this vital waterway.
  • Old Saybrook Country Club: Enjoy a round of golf at this picturesque course, offering a challenging game amid lush surroundings in the nearby region.
  • Essex Steam Train & Riverboat: Embark on a nostalgic journey aboard historic trains and riverboats that provide a unique sightseeing adventure along the scenic Connecticut River.

Essex Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local waterways: Take advantage of the area's scenic river and harbor settings to enjoy boating, kayaking, or simply relaxing by the water during your stay.
  • Discover regional dining options: Savor fresh seafood and regional specialties at nearby eateries that highlight the culinary character of this charming destination.
  • Visit nearby cultural sites: Immerse yourself in the region’s history and art scene by exploring local museums or historical landmarks close to your vacation rental.
  • Plan outdoor adventures: Make the most of the area's natural beauty with activities like hiking, walking tours, or picnics in scenic parks surrounding this destination.

Transportation Options

  • Essex Station: This historic train station offers convenient rail connections to major cities, making travel to and from the area straightforward and comfortable.
  • Shuttle Services: Local shuttle services provide easy access within Essex and to nearby attractions, ensuring you can explore the region without hassle.
  • Car Rentals: Renting a car is a flexible option to navigate the scenic coastal region and reach your preferred vacation rentals with ease.
  • Public Transit: Bus services connect Essex to surrounding towns and transportation hubs, offering an affordable and practical way to travel here.»

Local Customs Options

  • Clambake Traditions: Participating in local clambakes is a cherished custom that reflects the region's maritime heritage and offers a unique culinary experience here.
  • Seaside Festivals: Attending seasonal festivals along the coast allows you to immerse yourself in the area's maritime culture and community spirit.
  • Historical Boat Tours: Engaging in guided boat tours provides insight into the area's rich nautical history and scenic waterways.
  • Heritage Preservation Events: Supporting local events focused on preserving historical landmarks helps you connect with the region’s proud past during your stay.

Frequently Asked Questions About Essex?

1. What are the top vacation rentals in Essex?

There are a lot of options in Essex. If you plan on staying in the Essex area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Essex:

2. How many Rentbyowner vacation rentals are available in Essex?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 17 in the Essex area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Essex. 

3. What is the cancellation policy for vacation rentals in Essex, Connecticut?

Cancellation policies vary depending on the property listing. You should review the specific terms outlined on the booking page or contact the property owner directly to understand the cancellation timeframe and any applicable fees.

4. Are there any hidden fees I should be aware of when booking a vacation rental in this region?

Additional fees such as cleaning charges, service fees, or taxes may apply and are detailed during the booking process. To ensure transparency, read the full listing description and terms before confirming your reservation.

5. How do I find the most suitable vacation rental in Essex, Connecticut, for my stay?

Use search filters to narrow down options based on your preferred amenities, size, and budget. Always review the property details, photos, and guest reviews to make an informed decision suited to your needs.

6. What should I know about checking in and checking out at a vacation rental here?

Check-in and check-out procedures vary by property. Details are typically provided in the listing or sent after booking. Contact the property owner if you have specific questions about arrival times or key pickup instructions.

7. Is it safe to book a vacation rental in this destination during peak seasons?

Booking through reputable listings with verified reviews and direct communication with owners enhances safety. Ensure you read all property policies and reach out with any concerns before finalizing your reservation.