Holiday houses in Essex

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Top-rated holiday rentals in Essex

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Top Guest favourite

A sunset over the lake creates a vibrant display of pinks and purples reflected in the calm waters. The surrounding trees frame the scene, enhancing the tranquility of the natural landscape.

Cottage in Essex

Lakefront cottage for a fun, relaxing getaway.

Enjoy a cozy stay in a lake front cottage. Located in Essex, on chebacco lake, this 3 bedroom, 1.5 bathroom home has everything you could need. Fully stocked kitchen, comfortable living space with wifi and a large TV, and a comfy couch overlooking the lake. We have a external monitor with a keyboard and mouse to set up a workstation if needed. A large deck and seasonal dock to hang out on. Close to the ocean if you get tired of the lake. It's an excellent home base on Boston's North Shore.

4.96 out of 5 average rating, 130 reviews

Top Guest favourite

Apartment in Rockport

4 Bed Water View w/ 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.

4.99 out of 5 average rating, 175 reviews

Top Guest favourite

The contemporary tree house stands prominently against a clear blue sky, featuring expansive floor-to-ceiling windows that invite natural light. A vibrant blue staircase leads to the entrance. Lush greenery and carefully arranged landscaping enhance the modern design, creating a harmonious connection with nature.

Villa in Manchester-by-the-Sea

Secluded 20 Acre 10BR ultra contemporary Retreat

Family gatherings and family reunions. Make those family memories at this ultra contemporary take on a tree house. Original design based off the iconic Farnsworth house, updated with 10 Bed rooms of individual climate control atop of 20 acres of wildlife. Designer kitchen for the professional chef. Privacy that most movie stars long for. 5 min to beaches 10 min to Gloucester 20 min to historic Salem 45 min to Boston. Pesticide free landscaping Great location for family gatherings and reunions

4.97 out of 5 average rating, 75 reviews

Top Guest favourite

A welcoming living room features two grey sofas and a matching armchair, adorned with decorative pillows. A large area rug covers the hardwood floor, adding comfort. Natural light floods in through multiple windows, while a vibrant piece of artwork adds a touch of color to the space.

Townhouse in Essex

Cape Ann Gem close to Salem and beaches

Large beautifully restored and renovated 1888 colonial home with deep historical roots in Essex, on beautiful Cape Ann. This all 1 level completely renovated space offers 3 bedrooms, (with possible use of a 4th) full bathroom & loaded kitchen, original hardwood floors & details throughout. You'll be comfortable and at home able to enjoy all that beautiful Cape Ann has to offer - 15 minutes of SALEM. Conveniently location on the North Shore, easy access to SALEM, and IPSWICH for sure. WELCOME!

4.96 out of 5 average rating, 93 reviews

Top Guest favourite

A serene landscape showcases a sprawling marsh at sunset, with vibrant hues in the sky. Tall grasses and slender trees frame the scene, while a gentle waterway meanders through the lush greenery, providing a tranquil backdrop.

Condo in Essex

Marshside one-bedroom with stunning view

Convenient and sparkling clean, this fully furnished apartment is minutes from everything Cape Ann has to offer, but you might choose to stay put and enjoy the scenery instead! Enjoy the stunning marsh view with deer, hawks, osprey, and more, or head out to enjoy Cape Ann's other treasures. Located just off Rt. 133 in Essex, we're a short walk from the Essex County Greenbelt headquarters, a slightly longer walk from Conomo Point, and an easy drive to clam shacks, antiques, beaches, and more.

5.0 out of 5 average rating, 57 reviews

Guest favourite

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

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.

4.86 out of 5 average rating, 138 reviews

Top Guest favourite

A framed artwork features the silhouette of a raven against a shimmering gold background. The ornate frame adds a touch of elegance, enhancing the gothic decor of the space.

Condo in Salem

The Raven!

Looking for the quintessential Salem stay? Look no further! The main bedroom is designed to get you in the Salem spirit, with its dark gothic decor. Take a reading break in the adjacent room, outfitted to look like a Victorian British library. A spacious living room, dining room, kitchen, and full bath complete this lovely property. Enjoy parking in a driveway in the typically-packed city. We are just a quick and enjoyable 12-minute walk to Essex street and all that downtown has to offer!

4.96 out of 5 average rating, 124 reviews

Top Guest favourite

Apartment in Rockport

Oceanfront Retreat w/ Deck & Parking

• Private deck with ocean view • Parking • Steps to Front Beach • Walk to Bearskin Neck • Pet friendly • 15-minute walk to commuter rail • Contemporary art gallery on site Beautifully renovated, light-filled top-floor apartment on the water in historic downtown Rockport. Enjoy a private ocean-view deck, one dedicated parking space, and seasonal private access to Front Beach. One of three guest apartments at The Pearl, located just behind Thalassa, our contemporary art gallery.

4.99 out of 5 average rating, 93 reviews

Top Guest favourite

The living area is illuminated by natural light through the glass doors, showcasing a leather couch and a wooden coffee table. A chair and a modest decorative plant enhance the space, while sheer curtains softly diffuse the sunlight.

Apartment in Essex

R. Hill Tree Top Studio!

Minutes from the coast along a wooded road, this property greets you with nature and art. With a tree top view filtering amazing sunsets you feel away from it all. This property is a place to create. Home of a metal sculptor, art is woven into a lifestyle of art and nature. The nearby studio is an amazing place that welcomes visitors. Wake to the wonderful trees and landscape this property has, while staying in our newly renovated, thoughtfully designed & styled space.

5.0 out of 5 average rating, 85 reviews

Top Guest favourite

Apartment in Essex

Winter Rates ! Friendship Acres Barn Apartment B

Save up to 50% with winter rates Historic Barn conversion. Quiet peaceful country setting but within walking distance to town, restaurants and the Essex River. Best seafood around. Enjoy boating, kayaking, SUP or take a Essex River Cruise. An easy few minutes to historic Gloucester. Crane Beach is just a few minutes away. Experience the breathtaking coastline of Cape Ann. Hiking, history , whale watching and sightseeing. A short train ride to Boston and Salem

4.98 out of 5 average rating, 97 reviews

Top Guest favourite

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

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, no kitchenette, 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.

4.94 out of 5 average rating, 741 reviews

Top Guest favourite

A historic Colonial home is depicted with dark wooden siding and multiple windows. The structure features a central door, surrounded by evenly spaced windows on the front facade. Trees and greenery are visible in the surrounding yard, under a bright blue sky.

Home in Gloucester

William Haskell House First Period Colonial Home

A First Period Colonial American experience in beautiful Gloucester, Massachusetts! As you step through the threshold of this sensitively restored 1680 residence, you are transported to an earlier time—immersed in the history of the home and the area. This listing reserves all four rooms in the house: Parlor Chamber, North Ell, the Spinning Room and The Gambrell Bedroom. As well as access to the kitchen and lounge area that has a television.

5.0 out of 5 average rating, 37 reviews