Discover Your Ideal Essex County Vacation Rental to Make the Most of Your Massachusetts Getaway
Discover Your Perfect Essex County Vacation Homes
Best Vacation Homes in Essex County
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Essex County Luxury Rentals
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Essex County Pet Friendly Vacation Rentals
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Essex County Large Vacation Homes
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Why Choose Rent By Owner for your Essex County Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Essex County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, allowing you to enjoy the area's natural beauty and local charm at its best during your stay in Essex County, Massachusetts.
Peak Season Highlights
June to August
During the warm summer months, you can enjoy the bustling atmosphere and vibrant local events that make this destination lively and inviting.
September to October
Autumn brings colorful foliage and pleasant weather, making it an ideal time to explore outdoor activities and scenic views in the region.
Off-Season Highlights
November to February
The cooler winter months see fewer visitors, offering a peaceful retreat and the chance to enjoy cozy accommodations with fewer crowds.
March to May
Spring begins to awaken the area, but early season still features quieter streets and lower prices, perfect for those seeking tranquility.
Weekly Weather Forecast for Essex County
How to Book Your Essex County Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Essex County
Common Vacation Rentals Amenities
What amenities can you expect?
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 outdoor dining with a private patio or deck overlooking scenic views.
- Take advantage of a spacious backyard perfect for relaxing or outdoor activities.
- Make the most of a lovely garden area to unwind amidst lush greenery.
- Benefit from access to a fire pit ideal for cozy evenings under the stars.
- Utilize a private swimming pool to cool off during warm summer days.
- Explore nearby walking trails or nature paths directly from your rental property.
- Relax in a comfortable outdoor lounge area designed for enjoying the fresh air and sunshine.
Top Attractions Around Essex County
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities and cultural experiences just moments from your vacation rental, making it easy to explore the natural beauty and rich history that define Essex County, Massachusetts.

Family Activities
- Beach Time at Crane Beach: Spend a day relaxing and exploring the pristine sands and gentle waves of Crane Beach, a perfect spot for families to enjoy seaside activities in this scenic area.
- Museum of Fine Arts, Essex County: Engage with interactive exhibits and family-friendly programs that make exploring art and history enjoyable for visitors of all ages here in the region.
- Boat Tours and Cruises: Discover the beautiful waterways surrounding the coast through guided boat tours, offering a fun and educational experience for the whole family.
- Francis W. Parker Memorial Zoo: Visit this charming zoo where children can observe local wildlife and learn about conservation efforts within the area’s natural environment.
Adult Activities
- Boating and Sailing on Salem Harbor: Experience the thrill of exploring the scenic waters of Essex County by renting a boat or joining a sailing tour in this picturesque area.
- Wine Tasting at Local Vineyards: Discover the region’s renowned vineyards offering wine tastings and tours, perfect for relaxing and enjoying the local flavors.
- Historical Tours in Salem: Dive into the area's rich history with guided walking tours through historic Salem streets and landmarks that bring the past to life.
- Fishing Excursions in Coastal Waters: Engage in fishing trips along the coast, where you can enjoy the region’s abundant marine life and scenic views from a chartered vessel.
Other Places to Stay in Essex County, MA
Essex County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take the time to discover the area's hidden gems and popular sites to enrich your stay in Essex County, Massachusetts.
- Choose the Right Accommodation: Select a vacation rental that offers comfort and convenience, ideally located near the region's key points of interest.
- Plan Ahead for Outdoor Activities: Make the most of your visit by scheduling outdoor adventures that showcase the natural beauty of this destination.
- Experience Regional Cuisine: Savor local flavors at nearby eateries or prepare fresh ingredients in your vacation rental to enjoy authentic regional dishes.
Transportation Options
- Wildlife Sightseeing Cruises: You can explore the scenic waterways of Essex County through guided cruises that highlight the region's natural beauty and maritime heritage.
- Regional Bus Services: Public bus options offer convenient transportation across local towns, making it easy for you to visit various attractions within this area.
- Amtrak Train Service: The nearby train stations connect you to major cities and provide a comfortable way to reach the region without the hassle of driving.
- Private Car Rentals: Renting a car gives you the flexibility to discover hidden gems and explore the picturesque coast and countryside at your own pace here.
Local Customs Options
- Clam & Oyster Festivals: Participating in local clam and oyster festivals offers a taste of this area's rich maritime heritage while enjoying fresh seafood experiences.
- Sailing and Maritime Traditions: Embracing the region’s seafaring history, you might observe or partake in sailing events that are deeply rooted in here’s coastal culture.
- Historical Preservation Practices: Respect for historic sites and traditions is evident as communities preserve their colonial-era architecture and maritime museums.
- Local Seafood Cuisine: Savoring traditional seafood dishes reflects the area's culinary customs, emphasizing locally caught fish and shellfish specialties.
Frequently Asked Questions About Essex County?
1. What are the top vacation rentals in Essex County?
There are a lot of options in Essex County. If you plan on staying in the Essex County 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 County:
- Leslie's Retreat: Spacious home ideally located to everything
- Good Harbor Beach House - walk to beach, close to restaurants and shopping!
- 4 Bedroom LUX House/with Pool Next Door
- Artist's Studio turned Guest House Sleeps up to 3
- 'We can't wait to return to Four Winds'
- PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet
- PERIWINKLE COTTAGE #1 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet
- WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC
- Sweeping Harbor Views, Private Deck, Historic District, Walk To Everything!
- Marblehead. Cottage on Whittier, new construction
2. How many vacation rentals have private pools in Essex County?
There are 26 vacation rentals with private pools near Essex County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Essex County are best for families?
If you are looking for a family-friendly vacation home in Essex County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Essex County:
4. How many Rentbyowner vacation rentals are available in Essex County?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 1824 in the Essex County 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 County.
Essex County Top Rated Vacation Rentals
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