Vacation rentals in Essex County

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Top-rated vacation rentals in Essex County

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Guest favorite

French doors open into a cozy living area where a sectional sofa is visible. A small green table with a bouquet of flowers sits in front, while sunlight illuminates the space. Outside, garden views reveal lounge chairs and vibrant flowers.

Guesthouse in Gloucester

4.97 out of 5 average rating, 287 reviews

Annisquam Village Bunny Cottage

This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 minutes from Lighthouse Beach, Cambridge Beach and Talise Restaurant. Bunny Cottage has beautiful gardens, is surrounded by water on 3 sides, and has peek-a-boo views of Wingaersheek Beach from the bedroom window. The house is charming, with top notch amenities, like, heated floors, air conditioning (indoor/outdoor living). Mass Dept. of Revenue Certificate Number: #C0022781070

Top guest favorite

The open kitchen features a large island with seating for several guests. A cozy living area is visible, with a comfortable seating arrangement and large windows allowing natural light and ocean views. Warm wood flooring complements the airy atmosphere.

Apartment in Rockport

4.99 out of 5 average rating, 140 reviews

4 Bed 2.5 Bath Water view Downtown with Parking

Your family and friends will be close to everything when you stay at this centrally-located home. Steps to the Ocean and walk into historic Bearskin Neck. Enjoy panoramic coastal views from the family room, kitchen and master bedroom. Deck space to enjoy outdoor dining, glass of wine, or a morning cup of coffee. Everything to do in Rockport is a short walk from this downtown home. Restaurants and coffee shops, Art Galleries, shopping and the town beaches are steps away. Parking spots included.

Top guest favorite

A charming guest suite is visible amidst a well-kept yard, characterized by a blend of unique architectural elements. The structure features multiple windows and a welcoming entrance. Surrounding greenery and trees provide a sense of tranquility, enhancing the inviting outdoor space.

Guest suite in Beverly

5 out of 5 average rating, 128 reviews

Peaceful, 1888 Mediterranean Manor by the Beach

Architectural charm in this newly renovated, eco-friendly guest suite, could be a destination in itself with a granite kitchen, open living/dining, large yard, patio, private outdoor fireplace and fountain, and brick courtyard. A block away are beaches, lighthouse, playgrounds and a seaside park. Beverly has historic theatres, top-notch dining, cafes and microbrews. Boston is conveniently 30 mins away; other attractions like museums, castles, trails, water sports and whale watching are nearby.

Guest favorite

The charming exterior of an antique colonial-style home is displayed, featuring a yellow facade with dark green shutters. Flower boxes adorn the windows, filled with colorful blooms. A welcoming front entry is accentuated by steps leading up to the door, with a neatly landscaped garden visible.

Home in Salem

4.9 out of 5 average rating, 343 reviews

Henry Derby House

This antique home is perfect for families or wedding parties traveling together looking to explore downtown Salem. Experience the charm of Salem's McIntire district in the home originally built for tailor Henry Derby in 1838. This 7 bedroom 4 bathroom colonial style home will give you the feel of old Salem with some modern amenities in the updated kitchen and baths. The house is centrally located in walking distance to all of Salem's attractions as well as the T, but also off the beaten path.

Top guest favorite

The exterior of a historic brick home features a symmetrical facade with dark shutters and five windows. Two American flags hang from the center, above a welcoming entrance framed by decorative planters. Lush greenery complements the vibrant red brick, enhancing the building's classic appearance.

Guest suite in Salem

4.99 out of 5 average rating, 827 reviews

The Mason Suite of Salem

*We have THE BEST location in all of Salem! Take a look at our reviews!* The Mason Suite is a boutique lodging experience with all the comforts of home! Built in 1844 and nestled among Salem's most prized architecture, the Suite is just steps from the Witch Museum, bustle of the pedestrian mall, and Salem Common! Recently renovated from top to bottom! You'll be surrounded by fine furnishings, culture and history! The location is 10/10! We strive to provide you with the ideal Salem experience!

Top guest favorite

The exterior of the historic John Brewer house is shown, featuring a red wooden façade with multiple windows and flower boxes. An American flag is displayed prominently, and decorative elements like corn husks and seasonal flowers enhance the welcoming appearance. Sidewalks and roadways are visible in the foreground.

Apartment in Ipswich

4.99 out of 5 average rating, 175 reviews

Charming 2 Bedroom Apartment in Historic Ipswich.

In the heart of historic downtown Ipswich, the John Brewer house has been a family home since 1680! This fully renovated apartment features many modern amenities, like hi-speed internet, 50" and 55" televisions with streaming channels. There is parking for two cars, and we are a short walk to Market Street, the commuter rail to Boston, a large park for children, and many fantastic local restaurants. Drive to Boston or Maine in 45 mins; Salem or Gloucester in 30 mins; Crane Beach in 10 mins!

Guest favorite

An expansive view of the ocean showcases rolling waves under a partially cloudy sky. A deck is visible, outfitted with outdoor seating, surrounded by lush greenery and coastal vegetation, creating a serene outdoor space.

Apartment in Gloucester

4.86 out of 5 average rating, 121 reviews

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Top guest favorite

A well-lit sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light fills the room from multiple windows, complemented by a cozy seating nook and shelving that adds a charming touch to the serene atmosphere.

Apartment in Salem

4.98 out of 5 average rating, 411 reviews

Winter Island Retreat

Effective 4/1/23, NON Owner occupied listings have a 3% impact fee that is charged on the total expenses associated with the rental. Winter Island Retreat is a OWNER OCCUPIED listing that is the place; For total relaxation. Watch the sunrise and experience the Atlantic Ocean. Enjoy your favorite beverage while rocking in an Adirondack chair on the patio. Inhale the smell of the ocean breeze and fragrant sea roses. Winter Island Retreat is an experience like no other in the Witch City.

Top guest favorite

The living room is defined by vibrant purple walls and rich hardwood flooring. A large light blue sofa is accompanied by a red armchair and a central round table draped in a deep purple cloth. Colorful textiles and decorative accents add charm to the space.

Apartment in Salem

4.95 out of 5 average rating, 339 reviews

The Creaky Cauldron-Wizards and Witches Welcome!

Welcome to The Creaky Cauldron--an enchanting escape inspired by the world of witches and wizards--located in the heart of Salem! We have put a lot of love into creating a truly special and unique experience for visitors to the Witch City who love magic and Salem as much as we do. Each room has been carefully themed after a magical house or subject to give our guests an immersive experience. Each of our 7 rooms also reflects each of the 7 books in our favorite magical fantasy series.

Top guest favorite

A vibrant bedroom is presented, featuring a gold sun mural on a purple wall. An ornate headboard supports a spacious bed adorned with an orange and colorful patterned blanket. Decorative artwork and artifacts add character, while a unique lamp provides soft lighting.

Apartment in Salem

4.97 out of 5 average rating, 213 reviews

The Ghoul’s Attic-For 90s Witches and Wannabes

No ghoulies or ghosties here--just a unique and magical escape inspired by everyone's favorite school of magic--located upstairs at The Creaky Cauldron B&B in the heart of Salem! We have put a lot of love into creating a truly special and unique experience for visitors to the Witch City who love magic and Salem as much as we do. Each room has been carefully themed after a magical house and/or subject to give our guests an immersive experience in the world of witchcraft and wizardry.

Guest favorite

The exterior of the apartment is framed by lush greenery, showcasing a well-maintained lawn. A winding pathway leads to a red door framed by a white porch. Surrounding flowers add color amidst the soft shade of nearby trees, creating a serene atmosphere.

Apartment in Beverly

4.94 out of 5 average rating, 711 reviews

Beverly Farms Apartment “Homeport”

"Homeport" - A nautical themed apartment, nestled in the small coastal village of Beverly Farms. The village has cafes, restaurants, beaches and is nearby “Witch City” Salem MA. Homeport has a private entrance, den, two bedrooms, 1.5 baths with essential amenities and guest parking. The local area is famous for beaches, museums, galleries, eateries and many historic attractions. Explore the North Shore or take a commuter train to explore Boston, saving time and expense of driving.

Superhost

The spacious room features a king-sized bed with soft bedding and decorative pillows. Natural wood accents support a pitched ceiling, while a chandelier provides ambient lighting. A cozy gas fireplace and a flat-screen TV are visible. Large windows allow natural light and views of the surroundings.

Farm stay in North Andover

4.95 out of 5 average rating, 268 reviews

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!